diff --git a/api/v1/clusterextension_types.go b/api/v1/clusterextension_types.go
index 7b0a39ef1..05f3a9364 100644
--- a/api/v1/clusterextension_types.go
+++ b/api/v1/clusterextension_types.go
@@ -436,16 +436,14 @@ type CRDUpgradeSafetyPreflightConfig struct {
 }
 
 const (
-	// TypeDeprecated is a rollup condition that is present when
-	// any of the deprecated conditions are present.
+	// Deprecation Condition Types
 	TypeDeprecated        = "Deprecated"
 	TypePackageDeprecated = "PackageDeprecated"
 	TypeChannelDeprecated = "ChannelDeprecated"
 	TypeBundleDeprecated  = "BundleDeprecated"
 
-	// None will not perform CRD upgrade safety checks.
-	CRDUpgradeSafetyEnforcementNone CRDUpgradeSafetyEnforcement = "None"
-	// Strict will enforce the CRD upgrade safety check and block the upgrade if the CRD would not pass the check.
+	// CRD Upgrade Safety Enforcement
+	CRDUpgradeSafetyEnforcementNone   CRDUpgradeSafetyEnforcement = "None"
 	CRDUpgradeSafetyEnforcementStrict CRDUpgradeSafetyEnforcement = "Strict"
 )
 
diff --git a/api/v1/clusterextensionrevision_types.go b/api/v1/clusterextensionrevision_types.go
index 0f41ab319..ed5ff5bae 100644
--- a/api/v1/clusterextensionrevision_types.go
+++ b/api/v1/clusterextensionrevision_types.go
@@ -25,17 +25,18 @@ const (
 	ClusterExtensionRevisionKind = "ClusterExtensionRevision"
 
 	// Condition Types
-	ClusterExtensionRevisionTypeAvailable   = "Available"
-	ClusterExtensionRevisionTypeProgressing = "Progressing"
-	ClusterExtensionRevisionTypeSucceeded   = "Succeeded"
+	ClusterExtensionRevisionTypeReady = "Ready"
 
 	// Condition Reasons
-	ClusterExtensionRevisionReasonArchived        = "Archived"
-	ClusterExtensionRevisionReasonBlocked         = "Blocked"
-	ClusterExtensionRevisionReasonProbeFailure    = "ProbeFailure"
-	ClusterExtensionRevisionReasonProbesSucceeded = "ProbesSucceeded"
-	ClusterExtensionRevisionReasonReconciling     = "Reconciling"
-	ClusterExtensionRevisionReasonRetrying        = "Retrying"
+	ClusterExtensionRevisionReasonReady                    = "Ready"
+	ClusterExtensionRevisionReasonReconciling              = "Reconciling"
+	ClusterExtensionRevisionReasonProbeFailure             = "ProbeFailure"
+	ClusterExtensionRevisionReasonValidationFailed         = "ValidationFailed"
+	ClusterExtensionRevisionReasonObjectCollision          = "ObjectCollision"
+	ClusterExtensionRevisionReasonProgressDeadlineExceeded = "ProgressDeadlineExceeded"
+	ClusterExtensionRevisionReasonArchived                 = "Archived"
+	ClusterExtensionRevisionReasonRollingOut               = "RollingOut"
+	ClusterExtensionRevisionReasonTransitioning            = "Transitioning"
 )
 
 // ClusterExtensionRevisionSpec defines the desired state of ClusterExtensionRevision.
@@ -87,17 +88,6 @@ type ClusterExtensionRevisionSpec struct {
 	// +listMapKey=name
 	// +optional
 	Phases []ClusterExtensionRevisionPhase `json:"phases,omitempty"`
-
-	// progressDeadlineMinutes is an optional field that defines the maximum period
-	// of time in minutes after which an installation should be considered failed and
-	// require manual intervention. This functionality is disabled when no value
-	// is provided. The minimum period is 10 minutes, and the maximum is 720 minutes (12 hours).
-	//
-	// +kubebuilder:validation:Minimum:=10
-	// +kubebuilder:validation:Maximum:=720
-	// +optional
-	// <opcon:experimental>
-	ProgressDeadlineMinutes int32 `json:"progressDeadlineMinutes,omitempty"`
 }
 
 // ClusterExtensionRevisionLifecycleState specifies the lifecycle state of the ClusterExtensionRevision.
@@ -184,39 +174,106 @@ const (
 	CollisionProtectionNone CollisionProtection = "None"
 )
 
+// ClusterExtensionRevisionPhaseState represents the state of a phase during rollout.
+type ClusterExtensionRevisionPhaseState string
+
+const (
+	// ClusterExtensionRevisionPhaseStateApplied indicates all objects in the phase have been successfully applied.
+	ClusterExtensionRevisionPhaseStateApplied ClusterExtensionRevisionPhaseState = "Applied"
+	// ClusterExtensionRevisionPhaseStateProgressing indicates the phase is actively being reconciled and probes are being evaluated.
+	ClusterExtensionRevisionPhaseStateProgressing ClusterExtensionRevisionPhaseState = "Progressing"
+	// ClusterExtensionRevisionPhaseStateFailed indicates the phase has failed due to validation errors or collisions.
+	ClusterExtensionRevisionPhaseStateFailed ClusterExtensionRevisionPhaseState = "Failed"
+	// ClusterExtensionRevisionPhaseStatePending indicates the phase is waiting for previous phases to complete.
+	ClusterExtensionRevisionPhaseStatePending ClusterExtensionRevisionPhaseState = "Pending"
+	// ClusterExtensionRevisionPhaseStateTransitioning indicates objects in the phase are transitioning to a newer revision.
+	ClusterExtensionRevisionPhaseStateTransitioning ClusterExtensionRevisionPhaseState = "Transitioning"
+)
+
+// ClusterExtensionRevisionProbeFailure describes a failing probe for an object in a phase.
+type ClusterExtensionRevisionProbeFailure struct {
+	// kind is the Kind of the object failing probes.
+	// +required
+	Kind string `json:"kind"`
+
+	// name is the name of the object failing probes.
+	// +required
+	Name string `json:"name"`
+
+	// namespace is the namespace of the object failing probes.
+	// Empty for cluster-scoped objects.
+	// +optional
+	Namespace string `json:"namespace,omitempty"`
+
+	// message contains the joined probe failure messages.
+	// +required
+	Message string `json:"message"`
+}
+
+// ClusterExtensionRevisionPhaseStatus describes the status of a single phase.
+type ClusterExtensionRevisionPhaseStatus struct {
+	// name is the name of the phase.
+	// +required
+	Name string `json:"name"`
+
+	// state represents the current state of the phase.
+	// +required
+	// +kubebuilder:validation:Enum=Applied;Progressing;Failed;Pending;Transitioning
+	State ClusterExtensionRevisionPhaseState `json:"state"`
+
+	// message provides additional context about the phase state.
+	// This may include error messages for failed phases.
+	// +optional
+	Message string `json:"message,omitempty"`
+
+	// lastTransitionTime is the last time the phase state changed.
+	// This only updates when the state, message, or failingProbes change.
+	// +required
+	LastTransitionTime metav1.Time `json:"lastTransitionTime"`
+
+	// failingProbes lists objects in this phase that are failing their readiness probes.
+	// Only populated when state is Progressing and probes are failing.
+	// +optional
+	// +listType=atomic
+	FailingProbes []ClusterExtensionRevisionProbeFailure `json:"failingProbes,omitempty"`
+}
+
 // ClusterExtensionRevisionStatus defines the observed state of a ClusterExtensionRevision.
 type ClusterExtensionRevisionStatus struct {
 	// conditions is an optional list of status conditions describing the state of the
 	// ClusterExtensionRevision.
 	//
-	// The Progressing condition represents whether the revision is actively rolling out:
-	//   - When status is True and reason is RollingOut, the ClusterExtensionRevision rollout is actively making progress and is in transition.
-	//   - When status is True and reason is Retrying, the ClusterExtensionRevision has encountered an error that could be resolved on subsequent reconciliation attempts.
-	//   - When status is True and reason is Succeeded, the ClusterExtensionRevision has reached the desired state.
-	//   - When status is False and reason is Blocked, the ClusterExtensionRevision has encountered an error that requires manual intervention for recovery.
+	// The Ready condition represents whether the revision has been successfully rolled out and is ready:
+	//   - When status is True and reason is Ready, all ClusterExtensionRevision resources have been applied and all progression probes are successful.
+	//   - When status is False and reason is RollingOut, the ClusterExtensionRevision rollout is actively making progress and objects are being applied.
+	//   - When status is False and reason is Reconciling, the ClusterExtensionRevision is being reconciled or retrying after an error.
+	//   - When status is False and reason is ProbeFailure, one or more objects are failing their readiness probes.
+	//   - When status is False and reason is ValidationFailed, the revision failed preflight validation checks.
+	//   - When status is False and reason is ObjectCollision, the revision encountered object ownership collisions.
+	//   - When status is False and reason is ProgressDeadlineExceeded, the revision has not completed within the specified progress deadline.
+	//   - When status is False and reason is Transitioning, the revision's objects are being transitioned to a newer revision.
 	//   - When status is False and reason is Archived, the ClusterExtensionRevision is archived and not being actively reconciled.
 	//
-	// The Available condition represents whether the revision has been successfully rolled out and is available:
-	//   - When status is True and reason is ProbesSucceeded, the ClusterExtensionRevision has been successfully rolled out and all objects pass their readiness probes.
-	//   - When status is False and reason is ProbeFailure, one or more objects are failing their readiness probes during rollout.
-	//   - When status is Unknown and reason is Reconciling, the ClusterExtensionRevision has encountered an error that prevented it from observing the probes.
-	//   - When status is Unknown and reason is Archived, the ClusterExtensionRevision has been archived and its objects have been torn down.
-	//   - When status is Unknown and reason is Migrated, the ClusterExtensionRevision was migrated from an existing release and object status probe results have not yet been observed.
-	//
-	// The Succeeded condition represents whether the revision has successfully completed its rollout:
-	//   - When status is True and reason is Succeeded, the ClusterExtensionRevision has successfully completed its rollout. This condition is set once and persists even if the revision later becomes unavailable.
-	//
 	// +listType=map
 	// +listMapKey=type
 	// +optional
 	Conditions []metav1.Condition `json:"conditions,omitempty"`
+
+	// phaseStatuses provides detailed status information for each phase in the revision.
+	// Each phase status includes the phase name, current state, any error messages,
+	// and details about failing probes if applicable.
+	//
+	// +listType=map
+	// +listMapKey=name
+	// +optional
+	PhaseStatuses []ClusterExtensionRevisionPhaseStatus `json:"phaseStatuses,omitempty"`
 }
 
 // +kubebuilder:object:root=true
 // +kubebuilder:resource:scope=Cluster
 // +kubebuilder:subresource:status
-// +kubebuilder:printcolumn:name="Available",type=string,JSONPath=`.status.conditions[?(@.type=='Available')].status`
-// +kubebuilder:printcolumn:name="Progressing",type=string,JSONPath=`.status.conditions[?(@.type=='Progressing')].status`
+// +kubebuilder:printcolumn:name="Ready",type=string,JSONPath=`.status.conditions[?(@.type=='Ready')].status`
+// +kubebuilder:printcolumn:name="Reason",type=string,JSONPath=`.status.conditions[?(@.type=='Ready')].reason`
 // +kubebuilder:printcolumn:name=Age,type=date,JSONPath=`.metadata.creationTimestamp`
 
 // ClusterExtensionRevision represents an immutable snapshot of Kubernetes objects
diff --git a/api/v1/validation_test.go b/api/v1/validation_test.go
index bbd755c3c..583dfe7af 100644
--- a/api/v1/validation_test.go
+++ b/api/v1/validation_test.go
@@ -88,52 +88,6 @@ func TestValidate(t *testing.T) {
 			},
 			want: want{valid: true},
 		},
-		"ClusterExtensionRevision: invalid progress deadline < 10": {
-			args: args{
-				object: ClusterExtensionRevisionSpec{
-					ProgressDeadlineMinutes: 9,
-				},
-			},
-			want: want{valid: false},
-		},
-		"ClusterExtensionRevision: valid progress deadline = 10": {
-			args: args{
-				object: ClusterExtensionRevisionSpec{
-					ProgressDeadlineMinutes: 10,
-				},
-			},
-			want: want{valid: true},
-		},
-		"ClusterExtensionRevision: valid progress deadline = 360": {
-			args: args{
-				object: ClusterExtensionRevisionSpec{
-					ProgressDeadlineMinutes: 360,
-				},
-			},
-			want: want{valid: true},
-		},
-		"ClusterExtensionRevision: valid progress deadline = 720": {
-			args: args{
-				object: ClusterExtensionRevisionSpec{
-					ProgressDeadlineMinutes: 720,
-				},
-			},
-			want: want{valid: true},
-		},
-		"ClusterExtensionRevision: invalid progress deadline > 720": {
-			args: args{
-				object: ClusterExtensionRevisionSpec{
-					ProgressDeadlineMinutes: 721,
-				},
-			},
-			want: want{valid: false},
-		},
-		"ClusterExtensionRevision: no progress deadline set": {
-			args: args{
-				object: ClusterExtensionRevisionSpec{},
-			},
-			want: want{valid: true},
-		},
 	} {
 		t.Run(name, func(t *testing.T) {
 			var obj client.Object
diff --git a/api/v1/zz_generated.deepcopy.go b/api/v1/zz_generated.deepcopy.go
index 0c5c67c16..50da78698 100644
--- a/api/v1/zz_generated.deepcopy.go
+++ b/api/v1/zz_generated.deepcopy.go
@@ -436,6 +436,42 @@ func (in *ClusterExtensionRevisionPhase) DeepCopy() *ClusterExtensionRevisionPha
 	return out
 }
 
+// DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
+func (in *ClusterExtensionRevisionPhaseStatus) DeepCopyInto(out *ClusterExtensionRevisionPhaseStatus) {
+	*out = *in
+	in.LastTransitionTime.DeepCopyInto(&out.LastTransitionTime)
+	if in.FailingProbes != nil {
+		in, out := &in.FailingProbes, &out.FailingProbes
+		*out = make([]ClusterExtensionRevisionProbeFailure, len(*in))
+		copy(*out, *in)
+	}
+}
+
+// DeepCopy is an autogenerated deepcopy function, copying the receiver, creating a new ClusterExtensionRevisionPhaseStatus.
+func (in *ClusterExtensionRevisionPhaseStatus) DeepCopy() *ClusterExtensionRevisionPhaseStatus {
+	if in == nil {
+		return nil
+	}
+	out := new(ClusterExtensionRevisionPhaseStatus)
+	in.DeepCopyInto(out)
+	return out
+}
+
+// DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
+func (in *ClusterExtensionRevisionProbeFailure) DeepCopyInto(out *ClusterExtensionRevisionProbeFailure) {
+	*out = *in
+}
+
+// DeepCopy is an autogenerated deepcopy function, copying the receiver, creating a new ClusterExtensionRevisionProbeFailure.
+func (in *ClusterExtensionRevisionProbeFailure) DeepCopy() *ClusterExtensionRevisionProbeFailure {
+	if in == nil {
+		return nil
+	}
+	out := new(ClusterExtensionRevisionProbeFailure)
+	in.DeepCopyInto(out)
+	return out
+}
+
 // DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
 func (in *ClusterExtensionRevisionSpec) DeepCopyInto(out *ClusterExtensionRevisionSpec) {
 	*out = *in
@@ -468,6 +504,13 @@ func (in *ClusterExtensionRevisionStatus) DeepCopyInto(out *ClusterExtensionRevi
 			(*in)[i].DeepCopyInto(&(*out)[i])
 		}
 	}
+	if in.PhaseStatuses != nil {
+		in, out := &in.PhaseStatuses, &out.PhaseStatuses
+		*out = make([]ClusterExtensionRevisionPhaseStatus, len(*in))
+		for i := range *in {
+			(*in)[i].DeepCopyInto(&(*out)[i])
+		}
+	}
 }
 
 // DeepCopy is an autogenerated deepcopy function, copying the receiver, creating a new ClusterExtensionRevisionStatus.
diff --git a/cmd/operator-controller/main.go b/cmd/operator-controller/main.go
index dd0bc98f6..3e99cecd1 100644
--- a/cmd/operator-controller/main.go
+++ b/cmd/operator-controller/main.go
@@ -632,6 +632,7 @@ func (c *boxcutterReconcilerConfigurator) Configure(ceReconciler *controllers.Cl
 		controllers.ResolveBundle(c.resolver, c.mgr.GetClient()),
 		controllers.UnpackBundle(c.imagePuller, c.imageCache),
 		controllers.ApplyBundleWithBoxcutter(appl.Apply),
+		controllers.CheckProgressDeadline(&ceReconciler.ProgressDeadlineCheckInFlight),
 	}
 
 	baseDiscoveryClient, err := discovery.NewDiscoveryClientForConfig(c.mgr.GetConfig())
@@ -751,6 +752,7 @@ func (c *helmReconcilerConfigurator) Configure(ceReconciler *controllers.Cluster
 		controllers.ResolveBundle(c.resolver, c.mgr.GetClient()),
 		controllers.UnpackBundle(c.imagePuller, c.imageCache),
 		controllers.ApplyBundle(appl),
+		controllers.CheckProgressDeadline(&ceReconciler.ProgressDeadlineCheckInFlight),
 	}
 
 	return nil
diff --git a/helm/olmv1/base/operator-controller/crd/experimental/olm.operatorframework.io_clusterextensionrevisions.yaml b/helm/olmv1/base/operator-controller/crd/experimental/olm.operatorframework.io_clusterextensionrevisions.yaml
index 31e267b30..73ecf1847 100644
--- a/helm/olmv1/base/operator-controller/crd/experimental/olm.operatorframework.io_clusterextensionrevisions.yaml
+++ b/helm/olmv1/base/operator-controller/crd/experimental/olm.operatorframework.io_clusterextensionrevisions.yaml
@@ -16,11 +16,11 @@ spec:
   scope: Cluster
   versions:
   - additionalPrinterColumns:
-    - jsonPath: .status.conditions[?(@.type=='Available')].status
-      name: Available
+    - jsonPath: .status.conditions[?(@.type=='Ready')].status
+      name: Ready
       type: string
-    - jsonPath: .status.conditions[?(@.type=='Progressing')].status
-      name: Progressing
+    - jsonPath: .status.conditions[?(@.type=='Ready')].reason
+      name: Reason
       type: string
     - jsonPath: .metadata.creationTimestamp
       name: Age
@@ -166,16 +166,6 @@ spec:
                 x-kubernetes-validations:
                 - message: phases is immutable
                   rule: self == oldSelf || oldSelf.size() == 0
-              progressDeadlineMinutes:
-                description: |-
-                  progressDeadlineMinutes is an optional field that defines the maximum period
-                  of time in minutes after which an installation should be considered failed and
-                  require manual intervention. This functionality is disabled when no value
-                  is provided. The minimum period is 10 minutes, and the maximum is 720 minutes (12 hours).
-                format: int32
-                maximum: 720
-                minimum: 10
-                type: integer
               revision:
                 description: |-
                   revision is a required, immutable sequence number representing a specific revision
@@ -202,22 +192,16 @@ spec:
                   conditions is an optional list of status conditions describing the state of the
                   ClusterExtensionRevision.
 
-                  The Progressing condition represents whether the revision is actively rolling out:
-                    - When status is True and reason is RollingOut, the ClusterExtensionRevision rollout is actively making progress and is in transition.
-                    - When status is True and reason is Retrying, the ClusterExtensionRevision has encountered an error that could be resolved on subsequent reconciliation attempts.
-                    - When status is True and reason is Succeeded, the ClusterExtensionRevision has reached the desired state.
-                    - When status is False and reason is Blocked, the ClusterExtensionRevision has encountered an error that requires manual intervention for recovery.
+                  The Ready condition represents whether the revision has been successfully rolled out and is ready:
+                    - When status is True and reason is Ready, all ClusterExtensionRevision resources have been applied and all progression probes are successful.
+                    - When status is False and reason is RollingOut, the ClusterExtensionRevision rollout is actively making progress and objects are being applied.
+                    - When status is False and reason is Reconciling, the ClusterExtensionRevision is being reconciled or retrying after an error.
+                    - When status is False and reason is ProbeFailure, one or more objects are failing their readiness probes.
+                    - When status is False and reason is ValidationFailed, the revision failed preflight validation checks.
+                    - When status is False and reason is ObjectCollision, the revision encountered object ownership collisions.
+                    - When status is False and reason is ProgressDeadlineExceeded, the revision has not completed within the specified progress deadline.
+                    - When status is False and reason is Transitioning, the revision's objects are being transitioned to a newer revision.
                     - When status is False and reason is Archived, the ClusterExtensionRevision is archived and not being actively reconciled.
-
-                  The Available condition represents whether the revision has been successfully rolled out and is available:
-                    - When status is True and reason is ProbesSucceeded, the ClusterExtensionRevision has been successfully rolled out and all objects pass their readiness probes.
-                    - When status is False and reason is ProbeFailure, one or more objects are failing their readiness probes during rollout.
-                    - When status is Unknown and reason is Reconciling, the ClusterExtensionRevision has encountered an error that prevented it from observing the probes.
-                    - When status is Unknown and reason is Archived, the ClusterExtensionRevision has been archived and its objects have been torn down.
-                    - When status is Unknown and reason is Migrated, the ClusterExtensionRevision was migrated from an existing release and object status probe results have not yet been observed.
-
-                  The Succeeded condition represents whether the revision has successfully completed its rollout:
-                    - When status is True and reason is Succeeded, the ClusterExtensionRevision has successfully completed its rollout. This condition is set once and persists even if the revision later becomes unavailable.
                 items:
                   description: Condition contains details for one aspect of the current
                     state of this API Resource.
@@ -276,6 +260,77 @@ spec:
                 x-kubernetes-list-map-keys:
                 - type
                 x-kubernetes-list-type: map
+              phaseStatuses:
+                description: |-
+                  phaseStatuses provides detailed status information for each phase in the revision.
+                  Each phase status includes the phase name, current state, any error messages,
+                  and details about failing probes if applicable.
+                items:
+                  description: ClusterExtensionRevisionPhaseStatus describes the status
+                    of a single phase.
+                  properties:
+                    failingProbes:
+                      description: |-
+                        failingProbes lists objects in this phase that are failing their readiness probes.
+                        Only populated when state is Progressing and probes are failing.
+                      items:
+                        description: ClusterExtensionRevisionProbeFailure describes
+                          a failing probe for an object in a phase.
+                        properties:
+                          kind:
+                            description: kind is the Kind of the object failing probes.
+                            type: string
+                          message:
+                            description: message contains the joined probe failure
+                              messages.
+                            type: string
+                          name:
+                            description: name is the name of the object failing probes.
+                            type: string
+                          namespace:
+                            description: |-
+                              namespace is the namespace of the object failing probes.
+                              Empty for cluster-scoped objects.
+                            type: string
+                        required:
+                        - kind
+                        - message
+                        - name
+                        type: object
+                      type: array
+                      x-kubernetes-list-type: atomic
+                    lastTransitionTime:
+                      description: |-
+                        lastTransitionTime is the last time the phase state changed.
+                        This only updates when the state, message, or failingProbes change.
+                      format: date-time
+                      type: string
+                    message:
+                      description: |-
+                        message provides additional context about the phase state.
+                        This may include error messages for failed phases.
+                      type: string
+                    name:
+                      description: name is the name of the phase.
+                      type: string
+                    state:
+                      description: state represents the current state of the phase.
+                      enum:
+                      - Applied
+                      - Progressing
+                      - Failed
+                      - Pending
+                      - Transitioning
+                      type: string
+                  required:
+                  - lastTransitionTime
+                  - name
+                  - state
+                  type: object
+                type: array
+                x-kubernetes-list-map-keys:
+                - name
+                x-kubernetes-list-type: map
             type: object
         type: object
     served: true
diff --git a/internal/operator-controller/applier/boxcutter.go b/internal/operator-controller/applier/boxcutter.go
index 5f10716c7..016fde897 100644
--- a/internal/operator-controller/applier/boxcutter.go
+++ b/internal/operator-controller/applier/boxcutter.go
@@ -222,9 +222,6 @@ func (r *SimpleRevisionGenerator) buildClusterExtensionRevision(
 			Phases:         PhaseSort(objects),
 		},
 	}
-	if p := ext.Spec.ProgressDeadlineMinutes; p > 0 {
-		cer.Spec.ProgressDeadlineMinutes = p
-	}
 	return cer
 }
 
@@ -337,8 +334,8 @@ func (m *BoxcutterStorageMigrator) ensureMigratedRevisionStatus(ctx context.Cont
 		if revisions[i].Spec.Revision != 1 {
 			continue
 		}
-		// Skip if already succeeded - status is already set correctly.
-		if meta.IsStatusConditionTrue(revisions[i].Status.Conditions, ocv1.ClusterExtensionRevisionTypeSucceeded) {
+		// Skip if already ready - status is already set correctly.
+		if meta.IsStatusConditionTrue(revisions[i].Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady) {
 			return nil
 		}
 		// Ensure revision 1 status is set correctly, including for previously migrated
@@ -377,7 +374,7 @@ func (m *BoxcutterStorageMigrator) findLatestDeployedRelease(ac helmclient.Actio
 	return latestDeployed, nil
 }
 
-// ensureRevisionStatus ensures the revision has the Succeeded status condition set.
+// ensureRevisionStatus ensures the revision has the Ready status condition set.
 // Returns nil if the status is already set or after successfully setting it.
 // Only sets status on revisions that were actually migrated from Helm (marked with MigratedFromHelmKey label).
 func (m *BoxcutterStorageMigrator) ensureRevisionStatus(ctx context.Context, rev *ocv1.ClusterExtensionRevision) error {
@@ -387,23 +384,23 @@ func (m *BoxcutterStorageMigrator) ensureRevisionStatus(ctx context.Context, rev
 	}
 
 	// Only set status if this revision was actually migrated from Helm.
-	// This prevents us from incorrectly marking normal Boxcutter revision 1 as succeeded
+	// This prevents us from incorrectly marking normal Boxcutter revision 1 as ready
 	// when it's still in progress.
 	if rev.Labels[labels.MigratedFromHelmKey] != "true" {
 		return nil
 	}
 
-	// Check if status is already set to Succeeded=True
-	if meta.IsStatusConditionTrue(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeSucceeded) {
+	// Check if status is already set to Ready=True
+	if meta.IsStatusConditionTrue(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady) {
 		return nil
 	}
 
-	// Set the Succeeded status condition
+	// Set the Ready status condition
 	meta.SetStatusCondition(&rev.Status.Conditions, metav1.Condition{
-		Type:               ocv1.ClusterExtensionRevisionTypeSucceeded,
+		Type:               ocv1.ClusterExtensionRevisionTypeReady,
 		Status:             metav1.ConditionTrue,
-		Reason:             ocv1.ReasonSucceeded,
-		Message:            "Revision succeeded - migrated from Helm release",
+		Reason:             ocv1.ClusterExtensionRevisionReasonReady,
+		Message:            "Revision ready - migrated from Helm release",
 		ObservedGeneration: rev.GetGeneration(),
 	})
 
diff --git a/internal/operator-controller/applier/boxcutter_test.go b/internal/operator-controller/applier/boxcutter_test.go
index f7c1298ce..ac31adc6e 100644
--- a/internal/operator-controller/applier/boxcutter_test.go
+++ b/internal/operator-controller/applier/boxcutter_test.go
@@ -27,7 +27,6 @@ import (
 	"k8s.io/apiserver/pkg/authentication/user"
 	"k8s.io/apiserver/pkg/authorization/authorizer"
 	k8scheme "k8s.io/client-go/kubernetes/scheme"
-	"k8s.io/utils/ptr"
 	"sigs.k8s.io/controller-runtime/pkg/client"
 	"sigs.k8s.io/controller-runtime/pkg/client/fake"
 	"sigs.k8s.io/controller-runtime/pkg/client/interceptor"
@@ -425,65 +424,6 @@ func Test_SimpleRevisionGenerator_AppliesObjectLabelsAndRevisionAnnotations(t *t
 	require.Equal(t, revAnnotations, rev.Annotations)
 }
 
-func Test_SimpleRevisionGenerator_PropagatesProgressDeadlineMinutes(t *testing.T) {
-	r := &FakeManifestProvider{
-		GetFn: func(b fs.FS, e *ocv1.ClusterExtension) ([]client.Object, error) {
-			return []client.Object{}, nil
-		},
-	}
-
-	b := applier.SimpleRevisionGenerator{
-		Scheme:           k8scheme.Scheme,
-		ManifestProvider: r,
-	}
-
-	type args struct {
-		progressDeadlineMinutes *int32
-	}
-	type want struct {
-		progressDeadlineMinutes int32
-	}
-	type testCase struct {
-		args args
-		want want
-	}
-	for name, tc := range map[string]testCase{
-		"propagates when set": {
-			args: args{
-				progressDeadlineMinutes: ptr.To(int32(10)),
-			},
-			want: want{
-				progressDeadlineMinutes: 10,
-			},
-		},
-		"do not propagate when unset": {
-			want: want{
-				progressDeadlineMinutes: 0,
-			},
-		},
-	} {
-		ext := &ocv1.ClusterExtension{
-			ObjectMeta: metav1.ObjectMeta{
-				Name: "test-extension",
-			},
-			Spec: ocv1.ClusterExtensionSpec{
-				Namespace:      "test-namespace",
-				ServiceAccount: ocv1.ServiceAccountReference{Name: "test-sa"},
-			},
-		}
-		empty := map[string]string{}
-		t.Run(name, func(t *testing.T) {
-			if pd := tc.args.progressDeadlineMinutes; pd != nil {
-				ext.Spec.ProgressDeadlineMinutes = *pd
-			}
-
-			rev, err := b.GenerateRevision(t.Context(), dummyBundle, ext, empty, empty)
-			require.NoError(t, err)
-			require.Equal(t, tc.want.progressDeadlineMinutes, rev.Spec.ProgressDeadlineMinutes)
-		})
-	}
-}
-
 func Test_SimpleRevisionGenerator_Failure(t *testing.T) {
 	r := &FakeManifestProvider{
 		GetFn: func(b fs.FS, e *ocv1.ClusterExtension) ([]client.Object, error) {
@@ -1352,7 +1292,7 @@ func TestBoxcutterStorageMigrator(t *testing.T) {
 
 		client.AssertExpectations(t)
 
-		// Verify the migrated revision has Succeeded=True status with Succeeded reason and a migration message
+		// Verify the migrated revision has Ready=True status with Succeeded reason and a migration message
 		statusWriter := client.Status().(*statusWriterMock)
 		require.True(t, statusWriter.updateCalled, "Status().Update() should be called during migration")
 		require.NotNil(t, statusWriter.updatedObj, "Updated object should not be nil")
@@ -1360,12 +1300,12 @@ func TestBoxcutterStorageMigrator(t *testing.T) {
 		rev, ok := statusWriter.updatedObj.(*ocv1.ClusterExtensionRevision)
 		require.True(t, ok, "Updated object should be a ClusterExtensionRevision")
 
-		succeededCond := apimeta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeSucceeded)
-		require.NotNil(t, succeededCond, "Succeeded condition should be set")
-		assert.Equal(t, metav1.ConditionTrue, succeededCond.Status, "Succeeded condition should be True")
-		assert.Equal(t, ocv1.ReasonSucceeded, succeededCond.Reason, "Reason should be Succeeded")
-		assert.Equal(t, "Revision succeeded - migrated from Helm release", succeededCond.Message, "Message should indicate Helm migration")
-		assert.Equal(t, int64(1), succeededCond.ObservedGeneration, "ObservedGeneration should match revision generation")
+		readyCond := apimeta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
+		require.NotNil(t, readyCond, "Ready condition should be set")
+		assert.Equal(t, metav1.ConditionTrue, readyCond.Status, "Ready condition should be True")
+		assert.Equal(t, ocv1.ClusterExtensionRevisionReasonReady, readyCond.Reason, "Reason should be Succeeded")
+		assert.Equal(t, "Revision ready - migrated from Helm release", readyCond.Message, "Message should indicate Helm migration")
+		assert.Equal(t, int64(1), readyCond.ObservedGeneration, "ObservedGeneration should match revision generation")
 	})
 
 	t.Run("does not create revision when revisions exist", func(t *testing.T) {
@@ -1400,9 +1340,9 @@ func TestBoxcutterStorageMigrator(t *testing.T) {
 			Status: ocv1.ClusterExtensionRevisionStatus{
 				Conditions: []metav1.Condition{
 					{
-						Type:   ocv1.ClusterExtensionRevisionTypeSucceeded,
+						Type:   ocv1.ClusterExtensionRevisionTypeReady,
 						Status: metav1.ConditionTrue,
-						Reason: ocv1.ReasonSucceeded,
+						Reason: ocv1.ClusterExtensionRevisionReasonReady,
 					},
 				},
 			},
@@ -1483,10 +1423,10 @@ func TestBoxcutterStorageMigrator(t *testing.T) {
 		rev, ok := statusWriter.updatedObj.(*ocv1.ClusterExtensionRevision)
 		require.True(t, ok, "Updated object should be a ClusterExtensionRevision")
 
-		succeededCond := apimeta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeSucceeded)
-		require.NotNil(t, succeededCond, "Succeeded condition should be set")
-		assert.Equal(t, metav1.ConditionTrue, succeededCond.Status, "Succeeded condition should be True")
-		assert.Equal(t, ocv1.ReasonSucceeded, succeededCond.Reason, "Reason should be Succeeded")
+		readyCond := apimeta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
+		require.NotNil(t, readyCond, "Ready condition should be set")
+		assert.Equal(t, metav1.ConditionTrue, readyCond.Status, "Ready condition should be True")
+		assert.Equal(t, ocv1.ClusterExtensionRevisionReasonReady, readyCond.Reason, "Reason should be Succeeded")
 	})
 
 	t.Run("updates status from False to True for migrated revision", func(t *testing.T) {
@@ -1507,8 +1447,8 @@ func TestBoxcutterStorageMigrator(t *testing.T) {
 			ObjectMeta: metav1.ObjectMeta{Name: "test123"},
 		}
 
-		// Migrated revision with Succeeded=False (e.g., from a previous failed status update attempt)
-		// This simulates a revision whose Succeeded condition should be corrected from False to True during migration.
+		// Migrated revision with Ready=False (e.g., from a previous failed status update attempt)
+		// This simulates a revision whose Ready condition should be corrected from False to True during migration.
 		existingRev := ocv1.ClusterExtensionRevision{
 			ObjectMeta: metav1.ObjectMeta{
 				Name:       "test-revision",
@@ -1523,7 +1463,7 @@ func TestBoxcutterStorageMigrator(t *testing.T) {
 			Status: ocv1.ClusterExtensionRevisionStatus{
 				Conditions: []metav1.Condition{
 					{
-						Type:   ocv1.ClusterExtensionRevisionTypeSucceeded,
+						Type:   ocv1.ClusterExtensionRevisionTypeReady,
 						Status: metav1.ConditionFalse, // Important: False, not missing
 						Reason: "InProgress",
 					},
@@ -1560,10 +1500,10 @@ func TestBoxcutterStorageMigrator(t *testing.T) {
 		rev, ok := statusWriter.updatedObj.(*ocv1.ClusterExtensionRevision)
 		require.True(t, ok, "Updated object should be a ClusterExtensionRevision")
 
-		succeededCond := apimeta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeSucceeded)
-		require.NotNil(t, succeededCond, "Succeeded condition should be set")
-		assert.Equal(t, metav1.ConditionTrue, succeededCond.Status, "Succeeded condition should be updated to True")
-		assert.Equal(t, ocv1.ReasonSucceeded, succeededCond.Reason, "Reason should be Succeeded")
+		readyCond := apimeta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
+		require.NotNil(t, readyCond, "Ready condition should be set")
+		assert.Equal(t, metav1.ConditionTrue, readyCond.Status, "Ready condition should be updated to True")
+		assert.Equal(t, ocv1.ClusterExtensionRevisionReasonReady, readyCond.Reason, "Reason should be Succeeded")
 	})
 
 	t.Run("does not set status on non-migrated revision 1", func(t *testing.T) {
@@ -1707,7 +1647,7 @@ func TestBoxcutterStorageMigrator(t *testing.T) {
 		assert.Equal(t, 2, brb.helmReleaseUsed.Version, "Should use version 2 (deployed), not version 3 (failed)")
 		assert.Equal(t, release.StatusDeployed, brb.helmReleaseUsed.Info.Status, "Should use deployed release")
 
-		// Verify the migrated revision has Succeeded=True status
+		// Verify the migrated revision has Ready=True status
 		statusWriter := client.Status().(*statusWriterMock)
 		require.True(t, statusWriter.updateCalled, "Status().Update() should be called during migration")
 		require.NotNil(t, statusWriter.updatedObj, "Updated object should not be nil")
@@ -1715,9 +1655,9 @@ func TestBoxcutterStorageMigrator(t *testing.T) {
 		rev, ok := statusWriter.updatedObj.(*ocv1.ClusterExtensionRevision)
 		require.True(t, ok, "Updated object should be a ClusterExtensionRevision")
 
-		succeededCond := apimeta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeSucceeded)
-		require.NotNil(t, succeededCond, "Succeeded condition should be set")
-		assert.Equal(t, metav1.ConditionTrue, succeededCond.Status, "Succeeded condition should be True")
+		readyCond := apimeta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
+		require.NotNil(t, readyCond, "Ready condition should be set")
+		assert.Equal(t, metav1.ConditionTrue, readyCond.Status, "Ready condition should be True")
 	})
 
 	t.Run("does not create revision when helm release is not deployed and no deployed history", func(t *testing.T) {
diff --git a/internal/operator-controller/controllers/boxcutter_reconcile_steps.go b/internal/operator-controller/controllers/boxcutter_reconcile_steps.go
index dfb5dad14..cea7f924a 100644
--- a/internal/operator-controller/controllers/boxcutter_reconcile_steps.go
+++ b/internal/operator-controller/controllers/boxcutter_reconcile_steps.go
@@ -23,8 +23,10 @@ import (
 	"fmt"
 	"io/fs"
 	"slices"
+	"strconv"
 
 	apimeta "k8s.io/apimachinery/pkg/api/meta"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	ctrl "sigs.k8s.io/controller-runtime"
 	"sigs.k8s.io/controller-runtime/pkg/client"
 	"sigs.k8s.io/controller-runtime/pkg/log"
@@ -38,7 +40,7 @@ type BoxcutterRevisionStatesGetter struct {
 	Reader client.Reader
 }
 
-func (d *BoxcutterRevisionStatesGetter) GetRevisionStates(ctx context.Context, ext *ocv1.ClusterExtension) (*RevisionStates, error) {
+func (d *BoxcutterRevisionStatesGetter) GetRevisionStates(ctx context.Context, ext *ocv1.ClusterExtension) (RevisionStates, error) {
 	// TODO: boxcutter applier has a nearly identical bit of code for listing and sorting revisions
 	//   only difference here is that it sorts in reverse order to start iterating with the most
 	//   recent revisions. We should consolidate to avoid code duplication.
@@ -52,7 +54,7 @@ func (d *BoxcutterRevisionStatesGetter) GetRevisionStates(ctx context.Context, e
 		return cmp.Compare(a.Spec.Revision, b.Spec.Revision)
 	})
 
-	rs := &RevisionStates{}
+	var rs RevisionStates
 	for _, rev := range existingRevisionList.Items {
 		if rev.Spec.LifecycleState == ocv1.ClusterExtensionRevisionLifecycleStateArchived {
 			continue
@@ -61,22 +63,32 @@ func (d *BoxcutterRevisionStatesGetter) GetRevisionStates(ctx context.Context, e
 		// TODO: the setting of these annotations (happens in boxcutter applier when we pass in "revisionAnnotations")
 		//   is fairly decoupled from this code where we get the annotations back out. We may want to co-locate
 		//   the set/get logic a bit better to make it more maintainable and less likely to get out of sync.
+		state := RevisionStateRollingOut
+		if apimeta.IsStatusConditionTrue(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady) {
+			state = RevisionStateInstalled
+		}
+
+		generation := int64(0)
+		if genStr, ok := rev.Annotations[labels.ClusterExtensionGenerationKey]; ok {
+			if gen, err := strconv.ParseInt(genStr, 10, 64); err == nil {
+				generation = gen
+			}
+		}
+
 		rm := &RevisionMetadata{
-			RevisionName: rev.Name,
-			Package:      rev.Annotations[labels.PackageNameKey],
-			Image:        rev.Annotations[labels.BundleReferenceKey],
-			Conditions:   rev.Status.Conditions,
+			RevisionName:               rev.Name,
+			Package:                    rev.Annotations[labels.PackageNameKey],
+			Image:                      rev.Annotations[labels.BundleReferenceKey],
+			State:                      state,
+			ClusterExtensionGeneration: generation,
+			Conditions:                 rev.Status.Conditions,
 			BundleMetadata: ocv1.BundleMetadata{
 				Name:    rev.Annotations[labels.BundleNameKey],
 				Version: rev.Annotations[labels.BundleVersionKey],
 			},
 		}
 
-		if apimeta.IsStatusConditionTrue(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeSucceeded) {
-			rs.Installed = rm
-		} else {
-			rs.RollingOut = append(rs.RollingOut, rm)
-		}
+		rs = append(rs, rm)
 	}
 
 	return rs, nil
@@ -100,10 +112,11 @@ func ApplyBundleWithBoxcutter(apply func(ctx context.Context, contentFS fs.FS, e
 	return func(ctx context.Context, state *reconcileState, ext *ocv1.ClusterExtension) (*ctrl.Result, error) {
 		l := log.FromContext(ctx)
 		revisionAnnotations := map[string]string{
-			labels.BundleNameKey:      state.resolvedRevisionMetadata.Name,
-			labels.PackageNameKey:     state.resolvedRevisionMetadata.Package,
-			labels.BundleVersionKey:   state.resolvedRevisionMetadata.Version,
-			labels.BundleReferenceKey: state.resolvedRevisionMetadata.Image,
+			labels.BundleNameKey:                 state.resolvedRevisionMetadata.Name,
+			labels.PackageNameKey:                state.resolvedRevisionMetadata.Package,
+			labels.BundleVersionKey:              state.resolvedRevisionMetadata.Version,
+			labels.BundleReferenceKey:            state.resolvedRevisionMetadata.Image,
+			labels.ClusterExtensionGenerationKey: fmt.Sprintf("%d", ext.GetGeneration()),
 		}
 		objLbls := map[string]string{
 			labels.OwnerKindKey: ocv1.ClusterExtensionKind,
@@ -126,38 +139,49 @@ func ApplyBundleWithBoxcutter(apply func(ctx context.Context, contentFS fs.FS, e
 		}
 
 		ext.Status.ActiveRevisions = []ocv1.RevisionStatus{}
-		// Mirror Available/Progressing conditions from the installed revision
-		if i := state.revisionStates.Installed; i != nil {
-			for _, cndType := range []string{ocv1.ClusterExtensionRevisionTypeAvailable, ocv1.ClusterExtensionRevisionTypeProgressing} {
-				if cnd := apimeta.FindStatusCondition(i.Conditions, cndType); cnd != nil {
-					cnd.ObservedGeneration = ext.GetGeneration()
-					apimeta.SetStatusCondition(&ext.Status.Conditions, *cnd)
-				}
+		// Mirror Ready condition from the installed revision
+		if i := state.revisionStates.Installed(); i != nil {
+			if cnd := apimeta.FindStatusCondition(i.Conditions, ocv1.ClusterExtensionRevisionTypeReady); cnd != nil {
+				cnd.ObservedGeneration = ext.GetGeneration()
+				apimeta.SetStatusCondition(&ext.Status.Conditions, *cnd)
 			}
 			ext.Status.Install = &ocv1.ClusterExtensionInstallStatus{
 				Bundle: i.BundleMetadata,
 			}
 			ext.Status.ActiveRevisions = []ocv1.RevisionStatus{{Name: i.RevisionName}}
 		}
-		for idx, r := range state.revisionStates.RollingOut {
+		for idx, r := range state.revisionStates.RollingOut() {
 			rs := ocv1.RevisionStatus{Name: r.RevisionName}
-			for _, cndType := range []string{ocv1.ClusterExtensionRevisionTypeAvailable, ocv1.ClusterExtensionRevisionTypeProgressing} {
-				if cnd := apimeta.FindStatusCondition(r.Conditions, cndType); cnd != nil {
-					cnd.ObservedGeneration = ext.GetGeneration()
-					apimeta.SetStatusCondition(&rs.Conditions, *cnd)
-				}
+			if cnd := apimeta.FindStatusCondition(r.Conditions, ocv1.ClusterExtensionRevisionTypeReady); cnd != nil {
+				cnd.ObservedGeneration = ext.GetGeneration()
+				apimeta.SetStatusCondition(&rs.Conditions, *cnd)
 			}
-			// Mirror Progressing condition from the latest active revision
-			if idx == len(state.revisionStates.RollingOut)-1 {
-				if pcnd := apimeta.FindStatusCondition(r.Conditions, ocv1.ClusterExtensionRevisionTypeProgressing); pcnd != nil {
-					pcnd.ObservedGeneration = ext.GetGeneration()
-					apimeta.SetStatusCondition(&ext.Status.Conditions, *pcnd)
+			// Mirror Ready condition from the latest active revision
+			if idx == len(state.revisionStates.RollingOut())-1 {
+				if rcnd := apimeta.FindStatusCondition(r.Conditions, ocv1.ClusterExtensionRevisionTypeReady); rcnd != nil {
+					rcnd.ObservedGeneration = ext.GetGeneration()
+					apimeta.SetStatusCondition(&ext.Status.Conditions, *rcnd)
 				}
 			}
 			ext.Status.ActiveRevisions = append(ext.Status.ActiveRevisions, rs)
 		}
 
 		setInstalledStatusFromRevisionStates(ext, state.revisionStates)
+
+		// Set Progressing condition based on revision states
+		// If there's an installed revision and no rolling revisions, we've reached the desired state
+		if state.revisionStates.Installed() != nil && len(state.revisionStates.RollingOut()) == 0 {
+			setStatusProgressing(ext, nil)
+		} else {
+			// There are rolling revisions, so we're still progressing
+			SetStatusCondition(&ext.Status.Conditions, metav1.Condition{
+				Type:               ocv1.TypeProgressing,
+				Status:             metav1.ConditionTrue,
+				Reason:             ocv1.ReasonRollingOut,
+				Message:            "Rolling out new revision",
+				ObservedGeneration: ext.GetGeneration(),
+			})
+		}
 		return nil, nil
 	}
 }
diff --git a/internal/operator-controller/controllers/boxcutter_reconcile_steps_apply_test.go b/internal/operator-controller/controllers/boxcutter_reconcile_steps_apply_test.go
index 78adb7009..ece84e1fb 100644
--- a/internal/operator-controller/controllers/boxcutter_reconcile_steps_apply_test.go
+++ b/internal/operator-controller/controllers/boxcutter_reconcile_steps_apply_test.go
@@ -31,7 +31,7 @@ import (
 func TestApplyBundleWithBoxcutter(t *testing.T) {
 	type args struct {
 		activeRevisions []ocv1.RevisionStatus
-		revisionStates  *RevisionStates
+		revisionStates  RevisionStates
 	}
 	type want struct {
 		activeRevisions []ocv1.RevisionStatus
@@ -48,16 +48,18 @@ func TestApplyBundleWithBoxcutter(t *testing.T) {
 				activeRevisions: []ocv1.RevisionStatus{
 					{Name: "ce-1"},
 				},
-				revisionStates: &RevisionStates{
-					Installed: &RevisionMetadata{
+				revisionStates: RevisionStates{
+					{
 						RevisionName: "ce-1",
+						State:        RevisionStateInstalled,
 						BundleMetadata: ocv1.BundleMetadata{
 							Name:    "test-bundle",
 							Version: "1.0.0",
 						},
 					},
-					RollingOut: []*RevisionMetadata{
-						{RevisionName: "ce-2"},
+					{
+						RevisionName: "ce-2",
+						State:        RevisionStateRollingOut,
 					},
 				},
 			},
@@ -74,9 +76,10 @@ func TestApplyBundleWithBoxcutter(t *testing.T) {
 				activeRevisions: []ocv1.RevisionStatus{
 					{Name: "ce-1"},
 				},
-				revisionStates: &RevisionStates{
-					Installed: &RevisionMetadata{
+				revisionStates: RevisionStates{
+					{
 						RevisionName: "ce-2",
+						State:        RevisionStateInstalled,
 						BundleMetadata: ocv1.BundleMetadata{
 							Name:    "test-bundle",
 							Version: "1.0.1",
@@ -96,9 +99,10 @@ func TestApplyBundleWithBoxcutter(t *testing.T) {
 				activeRevisions: []ocv1.RevisionStatus{
 					{Name: "ce-1"},
 				},
-				revisionStates: &RevisionStates{
-					RollingOut: []*RevisionMetadata{
-						{RevisionName: "ce-1"},
+				revisionStates: RevisionStates{
+					{
+						RevisionName: "ce-1",
+						State:        RevisionStateRollingOut,
 					},
 				},
 			},
diff --git a/internal/operator-controller/controllers/clusterextension_controller.go b/internal/operator-controller/controllers/clusterextension_controller.go
index a3fcf48f3..ee9c9ff70 100644
--- a/internal/operator-controller/controllers/clusterextension_controller.go
+++ b/internal/operator-controller/controllers/clusterextension_controller.go
@@ -22,7 +22,9 @@ import (
 	"fmt"
 	"io/fs"
 	"slices"
+	"strconv"
 	"strings"
+	"sync"
 
 	"github.com/go-logr/logr"
 	"helm.sh/helm/v3/pkg/release"
@@ -60,7 +62,7 @@ const (
 )
 
 type reconcileState struct {
-	revisionStates           *RevisionStates
+	revisionStates           RevisionStates
 	resolvedRevisionMetadata *RevisionMetadata
 	imageFS                  fs.FS
 }
@@ -100,6 +102,9 @@ func (steps *ReconcileSteps) Reconcile(ctx context.Context, ext *ocv1.ClusterExt
 type ClusterExtensionReconciler struct {
 	client.Client
 	ReconcileSteps ReconcileSteps
+	// ProgressDeadlineCheckInFlight tracks if we have queued up the reconciliation that detects eventual progress deadline issues
+	// key is ClusterExtension UID, value is boolean
+	ProgressDeadlineCheckInFlight sync.Map
 }
 
 type StorageMigrator interface {
@@ -114,7 +119,7 @@ type Applier interface {
 }
 
 type RevisionStatesGetter interface {
-	GetRevisionStates(ctx context.Context, ext *ocv1.ClusterExtension) (*RevisionStates, error)
+	GetRevisionStates(ctx context.Context, ext *ocv1.ClusterExtension) (RevisionStates, error)
 }
 
 // The operator controller needs to watch all the bundle objects and reconcile accordingly. Though not ideal, but these permissions are required.
@@ -496,24 +501,61 @@ func clusterExtensionRequestsForCatalog(c client.Reader, logger logr.Logger) crh
 	}
 }
 
+type RevisionState string
+
+const (
+	RevisionStateInstalled  RevisionState = "Installed"
+	RevisionStateRollingOut RevisionState = "RollingOut"
+)
+
 type RevisionMetadata struct {
-	RevisionName string
-	Package      string
-	Image        string
+	RevisionName               string
+	Package                    string
+	Image                      string
+	State                      RevisionState
+	ClusterExtensionGeneration int64
 	ocv1.BundleMetadata
 	Conditions []metav1.Condition
 }
 
-type RevisionStates struct {
-	Installed  *RevisionMetadata
-	RollingOut []*RevisionMetadata
+// RevisionStates is a sorted list of active revision metadata, sorted ascending by revision number.
+// The last element is the most recent revision.
+type RevisionStates []*RevisionMetadata
+
+// Installed returns the installed revision metadata, or nil if none exists.
+func (rs RevisionStates) Installed() *RevisionMetadata {
+	for _, r := range rs {
+		if r.State == RevisionStateInstalled {
+			return r
+		}
+	}
+	return nil
+}
+
+// RollingOut returns all revisions that are currently rolling out.
+func (rs RevisionStates) RollingOut() []*RevisionMetadata {
+	var rolling []*RevisionMetadata
+	for _, r := range rs {
+		if r.State == RevisionStateRollingOut {
+			rolling = append(rolling, r)
+		}
+	}
+	return rolling
+}
+
+// Latest returns the most recent revision, or nil if there are no revisions.
+func (rs RevisionStates) Latest() *RevisionMetadata {
+	if len(rs) == 0 {
+		return nil
+	}
+	return rs[len(rs)-1]
 }
 
 type HelmRevisionStatesGetter struct {
 	helmclient.ActionClientGetter
 }
 
-func (d *HelmRevisionStatesGetter) GetRevisionStates(ctx context.Context, ext *ocv1.ClusterExtension) (*RevisionStates, error) {
+func (d *HelmRevisionStatesGetter) GetRevisionStates(ctx context.Context, ext *ocv1.ClusterExtension) (RevisionStates, error) {
 	cl, err := d.ActionClientFor(ctx, ext)
 	if err != nil {
 		return nil, err
@@ -523,7 +565,8 @@ func (d *HelmRevisionStatesGetter) GetRevisionStates(ctx context.Context, ext *o
 	if err != nil && !errors.Is(err, driver.ErrReleaseNotFound) {
 		return nil, err
 	}
-	rs := &RevisionStates{}
+
+	var rs RevisionStates
 	if len(relhis) == 0 {
 		return rs, nil
 	}
@@ -532,14 +575,23 @@ func (d *HelmRevisionStatesGetter) GetRevisionStates(ctx context.Context, ext *o
 	// But we need to look for the most-recent _Deployed_ release
 	for _, rel := range relhis {
 		if rel.Info != nil && rel.Info.Status == release.StatusDeployed {
-			rs.Installed = &RevisionMetadata{
-				Package: rel.Labels[labels.PackageNameKey],
-				Image:   rel.Labels[labels.BundleReferenceKey],
+			generation := int64(0)
+			if genStr, ok := rel.Labels[labels.ClusterExtensionGenerationKey]; ok {
+				if gen, err := strconv.ParseInt(genStr, 10, 64); err == nil {
+					generation = gen
+				}
+			}
+
+			rs = RevisionStates{&RevisionMetadata{
+				Package:                    rel.Labels[labels.PackageNameKey],
+				Image:                      rel.Labels[labels.BundleReferenceKey],
+				State:                      RevisionStateInstalled,
+				ClusterExtensionGeneration: generation,
 				BundleMetadata: ocv1.BundleMetadata{
 					Name:    rel.Labels[labels.BundleNameKey],
 					Version: rel.Labels[labels.BundleVersionKey],
 				},
-			}
+			}}
 			break
 		}
 	}
diff --git a/internal/operator-controller/controllers/clusterextension_controller_test.go b/internal/operator-controller/controllers/clusterextension_controller_test.go
index 28d766ace..c5a0296b5 100644
--- a/internal/operator-controller/controllers/clusterextension_controller_test.go
+++ b/internal/operator-controller/controllers/clusterextension_controller_test.go
@@ -280,9 +280,10 @@ func TestClusterExtensionUpgradeShowsInstalledBundleDeprecation(t *testing.T) {
 				}, nil
 		})
 		d.RevisionStatesGetter = &MockRevisionStatesGetter{
-			RevisionStates: &controllers.RevisionStates{
-				Installed: &controllers.RevisionMetadata{
+			RevisionStates: controllers.RevisionStates{
+				{
 					Package: pkgName,
+					State:   controllers.RevisionStateInstalled,
 					BundleMetadata: ocv1.BundleMetadata{
 						Name:    installedBundleName, // v1.0.0 installed
 						Version: "1.0.0",
@@ -365,9 +366,10 @@ func TestClusterExtensionResolutionFailsWithoutCatalogDeprecationData(t *testing
 		})
 
 		d.RevisionStatesGetter = &MockRevisionStatesGetter{
-			RevisionStates: &controllers.RevisionStates{
-				Installed: &controllers.RevisionMetadata{
+			RevisionStates: controllers.RevisionStates{
+				{
 					Package: pkgName,
+					State:   controllers.RevisionStateInstalled,
 					BundleMetadata: ocv1.BundleMetadata{
 						Name:    installedBundleName,
 						Version: "1.0.0",
@@ -681,8 +683,11 @@ func TestClusterExtensionBoxcutterApplierFailsDoesNotLeakDeprecationErrors(t *te
 		// Boxcutter keeps a rolling revision when apply fails. We mirror that state so the test uses
 		// the same inputs the runtime would see.
 		d.RevisionStatesGetter = &MockRevisionStatesGetter{
-			RevisionStates: &controllers.RevisionStates{
-				RollingOut: []*controllers.RevisionMetadata{{}},
+			RevisionStates: controllers.RevisionStates{
+				{
+					State:                      controllers.RevisionStateRollingOut,
+					ClusterExtensionGeneration: 1, // Match the ClusterExtension generation
+				},
 			},
 		}
 		d.Resolver = resolve.Func(func(ctx context.Context, ext *ocv1.ClusterExtension, installedBundle *ocv1.BundleMetadata) (*declcfg.Bundle, *bundle.VersionRelease, *declcfg.Deprecation, error) {
@@ -843,8 +848,9 @@ func TestClusterExtensionApplierFailsWithBundleInstalled(t *testing.T) {
 		})
 
 		d.RevisionStatesGetter = &MockRevisionStatesGetter{
-			RevisionStates: &controllers.RevisionStates{
-				Installed: &controllers.RevisionMetadata{
+			RevisionStates: controllers.RevisionStates{
+				{
+					State:          controllers.RevisionStateInstalled,
 					BundleMetadata: ocv1.BundleMetadata{Name: "prometheus.v1.0.0", Version: "1.0.0"},
 					Image:          "quay.io/operatorhubio/prometheus@fake1.0.0",
 				},
@@ -1181,8 +1187,9 @@ func TestClusterExtensionDeleteFinalizerFails(t *testing.T) {
 			installCompleted: true,
 		}
 		d.RevisionStatesGetter = &MockRevisionStatesGetter{
-			RevisionStates: &controllers.RevisionStates{
-				Installed: &controllers.RevisionMetadata{
+			RevisionStates: controllers.RevisionStates{
+				{
+					State:          controllers.RevisionStateInstalled,
 					BundleMetadata: ocv1.BundleMetadata{Name: "prometheus.v1.0.0", Version: "1.0.0"},
 					Image:          "quay.io/operatorhubio/prometheus@fake1.0.0",
 				},
@@ -2380,6 +2387,7 @@ func TestGetInstalledBundleHistory(t *testing.T) {
 			},
 			nil,
 			&controllers.RevisionMetadata{
+				State: controllers.RevisionStateInstalled,
 				BundleMetadata: ocv1.BundleMetadata{
 					Name:    "test-ext",
 					Version: "1.0",
@@ -2415,6 +2423,7 @@ func TestGetInstalledBundleHistory(t *testing.T) {
 			},
 			nil,
 			&controllers.RevisionMetadata{
+				State: controllers.RevisionStateInstalled,
 				BundleMetadata: ocv1.BundleMetadata{
 					Name:    "test-ext",
 					Version: "1.0",
@@ -2433,8 +2442,8 @@ func TestGetInstalledBundleHistory(t *testing.T) {
 			require.Nil(t, md)
 		} else {
 			require.NoError(t, err)
-			require.Equal(t, tst.expectedInstalled, md.Installed)
-			require.Nil(t, md.RollingOut)
+			require.Equal(t, tst.expectedInstalled, md.Installed())
+			require.Empty(t, md.RollingOut())
 		}
 	}
 }
@@ -2467,9 +2476,10 @@ func TestResolutionFallbackToInstalledBundle(t *testing.T) {
 			}
 			d.ImagePuller = &imageutil.MockPuller{ImageFS: fstest.MapFS{}}
 			d.RevisionStatesGetter = &MockRevisionStatesGetter{
-				RevisionStates: &controllers.RevisionStates{
-					Installed: &controllers.RevisionMetadata{
+				RevisionStates: controllers.RevisionStates{
+					{
 						Package:        "test-pkg",
+						State:          controllers.RevisionStateInstalled,
 						BundleMetadata: ocv1.BundleMetadata{Name: "test.1.0.0", Version: "1.0.0"},
 						Image:          "test-image:1.0.0",
 					},
@@ -2553,8 +2563,9 @@ func TestResolutionFallbackToInstalledBundle(t *testing.T) {
 				return nil, nil, nil, fmt.Errorf("catalog unavailable")
 			})
 			d.RevisionStatesGetter = &MockRevisionStatesGetter{
-				RevisionStates: &controllers.RevisionStates{
-					Installed: &controllers.RevisionMetadata{
+				RevisionStates: controllers.RevisionStates{
+					{
+						State:          controllers.RevisionStateInstalled,
 						BundleMetadata: ocv1.BundleMetadata{Name: "test.1.0.0", Version: "1.0.0"},
 					},
 				},
@@ -2624,9 +2635,10 @@ func TestResolutionFallbackToInstalledBundle(t *testing.T) {
 				}, &v, &declcfg.Deprecation{}, nil
 			})
 			d.RevisionStatesGetter = &MockRevisionStatesGetter{
-				RevisionStates: &controllers.RevisionStates{
-					Installed: &controllers.RevisionMetadata{
+				RevisionStates: controllers.RevisionStates{
+					{
 						Package:        "test-pkg",
+						State:          controllers.RevisionStateInstalled,
 						BundleMetadata: ocv1.BundleMetadata{Name: "test.1.0.0", Version: "1.0.0"},
 						Image:          "test-image:1.0.0",
 					},
@@ -2711,9 +2723,10 @@ func TestResolutionFallbackToInstalledBundle(t *testing.T) {
 				return nil, nil, nil, fmt.Errorf("transient catalog issue: cache stale")
 			})
 			d.RevisionStatesGetter = &MockRevisionStatesGetter{
-				RevisionStates: &controllers.RevisionStates{
-					Installed: &controllers.RevisionMetadata{
+				RevisionStates: controllers.RevisionStates{
+					{
 						Package:        "test-pkg",
+						State:          controllers.RevisionStateInstalled,
 						BundleMetadata: ocv1.BundleMetadata{Name: "test.1.0.0", Version: "1.0.0"},
 						Image:          "test-image:1.0.0",
 					},
diff --git a/internal/operator-controller/controllers/clusterextension_reconcile_steps.go b/internal/operator-controller/controllers/clusterextension_reconcile_steps.go
index 16d691f8b..bf1b25705 100644
--- a/internal/operator-controller/controllers/clusterextension_reconcile_steps.go
+++ b/internal/operator-controller/controllers/clusterextension_reconcile_steps.go
@@ -20,6 +20,8 @@ import (
 	"context"
 	"errors"
 	"fmt"
+	"sync"
+	"time"
 
 	apimeta "k8s.io/apimachinery/pkg/api/meta"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
@@ -95,31 +97,40 @@ func RetrieveRevisionStates(r RevisionStatesGetter) ReconcileStepFunc {
 func ResolveBundle(r resolve.Resolver, c client.Client) ReconcileStepFunc {
 	return func(ctx context.Context, state *reconcileState, ext *ocv1.ClusterExtension) (*ctrl.Result, error) {
 		l := log.FromContext(ctx)
-
-		// If already rolling out, use existing revision and set deprecation to Unknown (no catalog check)
-		if len(state.revisionStates.RollingOut) > 0 {
-			installedBundleName := ""
-			if state.revisionStates.Installed != nil {
-				installedBundleName = state.revisionStates.Installed.Name
+		l.Info("resolving bundle")
+
+		// If the latest revision is already rolling out for the current generation, skip resolution
+		// This prevents re-resolving when a revision is already being deployed for the current spec
+		if latest := state.revisionStates.Latest(); latest != nil {
+			if latest.State == RevisionStateRollingOut && latest.ClusterExtensionGeneration == ext.GetGeneration() {
+				l.Info("skipping resolver - latest revision already rolling out for current generation",
+					"revisionName", latest.RevisionName,
+					"generation", ext.GetGeneration())
+				installedBundleName := ""
+				if state.revisionStates.Installed() != nil {
+					l.Info("installed bundle", "name", state.revisionStates.Installed().Name)
+					installedBundleName = state.revisionStates.Installed().Name
+				}
+				SetDeprecationStatus(ext, installedBundleName, nil, false)
+				state.resolvedRevisionMetadata = latest
+				return nil, nil
 			}
-			SetDeprecationStatus(ext, installedBundleName, nil, false)
-			state.resolvedRevisionMetadata = state.revisionStates.RollingOut[0]
-			return nil, nil
 		}
 
 		// Resolve a new bundle from the catalog
 		l.V(1).Info("resolving bundle")
 		var bm *ocv1.BundleMetadata
-		if state.revisionStates.Installed != nil {
-			bm = &state.revisionStates.Installed.BundleMetadata
+		if state.revisionStates.Installed() != nil {
+			l.Info("installed bundle", "name", state.revisionStates.Installed().Name)
+			bm = &state.revisionStates.Installed().BundleMetadata
 		}
 		resolvedBundle, resolvedBundleVersion, resolvedDeprecation, err := r.Resolve(ctx, ext, bm)
 
 		// Get the installed bundle name for deprecation status.
 		// BundleDeprecated should reflect what's currently running, not what we're trying to install.
 		installedBundleName := ""
-		if state.revisionStates.Installed != nil {
-			installedBundleName = state.revisionStates.Installed.Name
+		if state.revisionStates.Installed() != nil {
+			installedBundleName = state.revisionStates.Installed().Name
 		}
 
 		// Set deprecation status based on resolution results:
@@ -142,9 +153,11 @@ func ResolveBundle(r resolve.Resolver, c client.Client) ReconcileStepFunc {
 			return handleResolutionError(ctx, c, state, ext, err)
 		}
 
+		l.Info("resolved bundle", "name", resolvedBundle.Name, "version", resolvedBundleVersion.Version.String(), "deprecation", resolvedDeprecation)
 		state.resolvedRevisionMetadata = &RevisionMetadata{
-			Package: resolvedBundle.Package,
-			Image:   resolvedBundle.Image,
+			Package:                    resolvedBundle.Package,
+			Image:                      resolvedBundle.Image,
+			ClusterExtensionGeneration: ext.GetGeneration(),
 			// TODO: Right now, operator-controller only supports registry+v1 bundles and has no concept
 			//   of a "release" field. If/when we add a release field concept or a new bundle format
 			//   we need to re-evaluate use of `AsLegacyRegistryV1Version` so that we avoid propagating
@@ -172,7 +185,7 @@ func handleResolutionError(ctx context.Context, c client.Client, state *reconcil
 	l := log.FromContext(ctx)
 
 	// No installed bundle and resolution failed - cannot proceed
-	if state.revisionStates.Installed == nil {
+	if state.revisionStates.Installed() == nil {
 		msg := fmt.Sprintf("failed to resolve bundle: %v", err)
 		setStatusProgressing(ext, err)
 		setInstalledStatusFromRevisionStates(ext, state.revisionStates)
@@ -185,7 +198,7 @@ func handleResolutionError(ctx context.Context, c client.Client, state *reconcil
 	if ext.Spec.Source.Catalog != nil {
 		specVersion = ext.Spec.Source.Catalog.Version
 	}
-	installedVersion := state.revisionStates.Installed.Version
+	installedVersion := state.revisionStates.Installed().Version
 
 	// If spec requests a different version, we cannot fall back - must fail and retry
 	if specVersion != "" && specVersion != installedVersion {
@@ -246,11 +259,11 @@ func handleResolutionError(ctx context.Context, c client.Client, state *reconcil
 		"resolutionError", err.Error(),
 		"packageName", getPackageName(ext),
 		"catalogName", catalogName,
-		"installedBundle", state.revisionStates.Installed.Name,
-		"installedVersion", state.revisionStates.Installed.Version)
+		"installedBundle", state.revisionStates.Installed().Name,
+		"installedVersion", state.revisionStates.Installed().Version)
 	// Set installed status based on current revision states (needed before Apply runs)
 	setInstalledStatusFromRevisionStates(ext, state.revisionStates)
-	state.resolvedRevisionMetadata = state.revisionStates.Installed
+	state.resolvedRevisionMetadata = state.revisionStates.Installed()
 	// Return no error to allow Apply step to run and maintain resources.
 	// Apply will set Progressing=Succeeded when it completes successfully.
 	return nil, nil
@@ -326,9 +339,9 @@ func UnpackBundle(i imageutil.Puller, cache imageutil.Cache) ReconcileStepFunc {
 
 		// Check if resolved bundle matches installed bundle (no version change)
 		bundleUnchanged := state.revisionStates != nil &&
-			state.revisionStates.Installed != nil &&
-			state.resolvedRevisionMetadata.Name == state.revisionStates.Installed.Name &&
-			state.resolvedRevisionMetadata.Version == state.revisionStates.Installed.Version
+			state.revisionStates.Installed() != nil &&
+			state.resolvedRevisionMetadata.Name == state.revisionStates.Installed().Name &&
+			state.resolvedRevisionMetadata.Version == state.revisionStates.Installed().Version
 
 		if err != nil {
 			if bundleUnchanged {
@@ -363,10 +376,11 @@ func ApplyBundle(a Applier) ReconcileStepFunc {
 	return func(ctx context.Context, state *reconcileState, ext *ocv1.ClusterExtension) (*ctrl.Result, error) {
 		l := log.FromContext(ctx)
 		revisionAnnotations := map[string]string{
-			labels.BundleNameKey:      state.resolvedRevisionMetadata.Name,
-			labels.PackageNameKey:     state.resolvedRevisionMetadata.Package,
-			labels.BundleVersionKey:   state.resolvedRevisionMetadata.Version,
-			labels.BundleReferenceKey: state.resolvedRevisionMetadata.Image,
+			labels.BundleNameKey:                 state.resolvedRevisionMetadata.Name,
+			labels.PackageNameKey:                state.resolvedRevisionMetadata.Package,
+			labels.BundleVersionKey:              state.resolvedRevisionMetadata.Version,
+			labels.BundleReferenceKey:            state.resolvedRevisionMetadata.Image,
+			labels.ClusterExtensionGenerationKey: fmt.Sprintf("%d", ext.GetGeneration()),
 		}
 		objLbls := map[string]string{
 			labels.OwnerKindKey: ocv1.ClusterExtensionKind,
@@ -387,9 +401,13 @@ func ApplyBundle(a Applier) ReconcileStepFunc {
 
 		// Set installed status
 		if rolloutSucceeded {
-			state.revisionStates = &RevisionStates{Installed: state.resolvedRevisionMetadata}
-		} else if err == nil && state.revisionStates.Installed == nil && len(state.revisionStates.RollingOut) == 0 {
-			state.revisionStates = &RevisionStates{RollingOut: []*RevisionMetadata{state.resolvedRevisionMetadata}}
+			rm := state.resolvedRevisionMetadata
+			rm.State = RevisionStateInstalled
+			state.revisionStates = RevisionStates{rm}
+		} else if err == nil && state.revisionStates.Installed() == nil && len(state.revisionStates.RollingOut()) == 0 {
+			rm := state.resolvedRevisionMetadata
+			rm.State = RevisionStateRollingOut
+			state.revisionStates = RevisionStates{rm}
 		}
 		setInstalledStatusFromRevisionStates(ext, state.revisionStates)
 
@@ -412,3 +430,86 @@ func ApplyBundle(a Applier) ReconcileStepFunc {
 		return nil, nil
 	}
 }
+
+// CheckProgressDeadline checks if the ClusterExtension has exceeded its progress deadline.
+// It monitors the Progressing condition and active revision Ready conditions to detect:
+//  1. Retrying transient errors (Progressing=True, Reason=Retrying): bundle resolution, image pull, API errors
+//  2. Stuck rollouts (Progressing=True, Reason=RollingOut): revisions failing to reach Ready state
+//
+// When the deadline is exceeded, it sets Progressing=False with Reason=ProgressDeadlineExceeded
+// to mark the failure as terminal. It tracks deadline checks per ClusterExtension UID to avoid
+// scheduling redundant requeues.
+func CheckProgressDeadline(progressDeadlineCheckInFlight *sync.Map) ReconcileStepFunc {
+	return func(ctx context.Context, state *reconcileState, ext *ocv1.ClusterExtension) (*ctrl.Result, error) {
+		l := log.FromContext(ctx)
+
+		pd := ext.Spec.ProgressDeadlineMinutes
+		if pd <= 0 {
+			// No progress deadline configured, clear tracking and skip check
+			progressDeadlineCheckInFlight.Delete(ext.GetUID())
+			return nil, nil
+		}
+
+		cnd := apimeta.FindStatusCondition(ext.Status.Conditions, ocv1.TypeProgressing)
+		// Check progress deadline for:
+		// 1. Transient errors (Progressing=True with Reason=Retrying): bundle resolution, image pull, API errors, etc.
+		// 2. Stuck rollouts (Progressing=True with Reason=RollingOut): revisions that fail to reach Ready state
+		// Terminal errors (Progressing=False) like configuration validation failures are already terminal.
+		isStuckRetrying := cnd != nil && cnd.Status == metav1.ConditionTrue && cnd.Reason == ocv1.ReasonRetrying
+		isRollingOut := cnd != nil && cnd.Status == metav1.ConditionTrue && cnd.Reason == ocv1.ReasonRollingOut
+
+		var timeSinceLastTransition time.Duration
+		var isStuck bool
+
+		if isStuckRetrying {
+			// Retrying transient errors - use Progressing condition's LastTransitionTime
+			timeSinceLastTransition = time.Since(cnd.LastTransitionTime.Time)
+			isStuck = true
+		} else if isRollingOut {
+			// Rolling out - check if the latest active revision is stuck
+			// The latest revision is the one currently rolling out
+			if len(ext.Status.ActiveRevisions) > 0 {
+				latestRevStatus := ext.Status.ActiveRevisions[len(ext.Status.ActiveRevisions)-1]
+				readyCond := apimeta.FindStatusCondition(latestRevStatus.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
+				if readyCond != nil && readyCond.Status == metav1.ConditionFalse {
+					// Latest revision is not ready - check how long it's been stuck
+					timeSinceLastTransition = time.Since(readyCond.LastTransitionTime.Time)
+					isStuck = true
+				}
+			}
+		}
+
+		if !isStuck {
+			// Not stuck anymore (either progressing successfully, or already terminal),
+			// clear the deadline check tracking
+			progressDeadlineCheckInFlight.Delete(ext.GetUID())
+			return nil, nil
+		}
+
+		timeout := time.Duration(pd) * time.Minute
+
+		if timeSinceLastTransition > timeout {
+			// Progress deadline exceeded - set terminal condition
+			l.Info("progress deadline exceeded", "deadline", pd, "timeSinceLastTransition", timeSinceLastTransition)
+			SetStatusCondition(&ext.Status.Conditions, metav1.Condition{
+				Type:               ocv1.TypeProgressing,
+				Status:             metav1.ConditionFalse,
+				Reason:             ocv1.ReasonProgressDeadlineExceeded,
+				Message:            fmt.Sprintf("ClusterExtension has not progressed for %d minutes", pd),
+				ObservedGeneration: ext.GetGeneration(),
+			})
+			// Return nil error and empty result since this is now terminal (no retry needed)
+			return &ctrl.Result{}, nil
+		}
+
+		// Deadline not yet exceeded - schedule a requeue to check again later
+		// Only schedule if we haven't already scheduled one for this ClusterExtension
+		if _, found := progressDeadlineCheckInFlight.Load(ext.GetUID()); !found {
+			progressDeadlineCheckInFlight.Store(ext.GetUID(), true)
+			timeUntilDeadline := timeout - timeSinceLastTransition
+			return &ctrl.Result{RequeueAfter: timeUntilDeadline}, nil
+		}
+
+		return nil, nil
+	}
+}
diff --git a/internal/operator-controller/controllers/clusterextensionrevision_controller.go b/internal/operator-controller/controllers/clusterextensionrevision_controller.go
index 138bcd8eb..c99237bad 100644
--- a/internal/operator-controller/controllers/clusterextensionrevision_controller.go
+++ b/internal/operator-controller/controllers/clusterextensionrevision_controller.go
@@ -8,7 +8,6 @@ import (
 	"errors"
 	"fmt"
 	"strings"
-	"sync"
 	"time"
 
 	appsv1 "k8s.io/api/apps/v1"
@@ -48,9 +47,6 @@ type ClusterExtensionRevisionReconciler struct {
 	Client                client.Client
 	RevisionEngineFactory RevisionEngineFactory
 	TrackingCache         trackingCache
-	// track if we have queued up the reconciliation that detects eventual progress deadline issues
-	// keys is revision UUID, value is boolean
-	progressDeadlineCheckInFlight sync.Map
 }
 
 type trackingCache interface {
@@ -79,25 +75,6 @@ func (c *ClusterExtensionRevisionReconciler) Reconcile(ctx context.Context, req
 	reconciledRev := existingRev.DeepCopy()
 	res, reconcileErr := c.reconcile(ctx, reconciledRev)
 
-	if pd := existingRev.Spec.ProgressDeadlineMinutes; pd > 0 {
-		cnd := meta.FindStatusCondition(reconciledRev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeProgressing)
-		isStillProgressing := cnd != nil && cnd.Status == metav1.ConditionTrue && cnd.Reason != ocv1.ReasonSucceeded
-		succeeded := meta.IsStatusConditionTrue(reconciledRev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeSucceeded)
-		// check if we reached the progress deadline only if the revision is still progressing and has not succeeded yet
-		if isStillProgressing && !succeeded {
-			timeout := time.Duration(pd) * time.Minute
-			if time.Since(existingRev.CreationTimestamp.Time) > timeout {
-				// progress deadline reached, reset any errors and stop reconciling this revision
-				markAsNotProgressing(reconciledRev, ocv1.ReasonProgressDeadlineExceeded, fmt.Sprintf("Revision has not rolled out for %d minutes.", pd))
-				reconcileErr = nil
-				res = ctrl.Result{}
-			} else if _, found := c.progressDeadlineCheckInFlight.Load(existingRev.GetUID()); !found && reconcileErr == nil {
-				// if we haven't already queued up a reconcile to check for progress deadline, queue one up, but only once
-				c.progressDeadlineCheckInFlight.Store(existingRev.GetUID(), true)
-				res = ctrl.Result{RequeueAfter: timeout}
-			}
-		}
-	}
 	// Do checks before any Update()s, as Update() may modify the resource structure!
 	updateStatus := !equality.Semantic.DeepEqual(existingRev.Status, reconciledRev.Status)
 
@@ -169,6 +146,7 @@ func (c *ClusterExtensionRevisionReconciler) reconcile(ctx context.Context, rev
 		if rres != nil {
 			// Log detailed reconcile reports only in debug mode (V(1)) to reduce verbosity.
 			l.V(1).Info("reconcile report", "report", rres.String())
+			updatePhaseStatuses(rev, rres)
 		}
 		setRetryingConditions(rev, err.Error())
 		return ctrl.Result{}, fmt.Errorf("revision reconcile: %v", err)
@@ -178,14 +156,24 @@ func (c *ClusterExtensionRevisionReconciler) reconcile(ctx context.Context, rev
 	// TODO: report status, backoff?
 	if verr := rres.GetValidationError(); verr != nil {
 		l.Error(fmt.Errorf("%w", verr), "preflight validation failed, retrying after 10s")
-		setRetryingConditions(rev, fmt.Sprintf("revision validation error: %s", verr))
+		updatePhaseStatuses(rev, rres)
+		markAsNotReady(rev, ocv1.ClusterExtensionRevisionReasonValidationFailed, fmt.Sprintf("revision validation error: %s", verr))
 		return ctrl.Result{RequeueAfter: 10 * time.Second}, nil
 	}
 
 	for i, pres := range rres.GetPhases() {
+		phaseName := ""
+		if i < len(rev.Spec.Phases) {
+			phaseName = rev.Spec.Phases[i].Name
+		}
+		if phaseName == "" {
+			phaseName = fmt.Sprintf("%d", i)
+		}
+
 		if verr := pres.GetValidationError(); verr != nil {
-			l.Error(fmt.Errorf("%w", verr), "phase preflight validation failed, retrying after 10s", "phase", i)
-			setRetryingConditions(rev, fmt.Sprintf("phase %d validation error: %s", i, verr))
+			l.Error(fmt.Errorf("%w", verr), "phase preflight validation failed, retrying after 10s", "phase", phaseName)
+			updatePhaseStatuses(rev, rres)
+			markAsNotReady(rev, ocv1.ClusterExtensionRevisionReasonValidationFailed, fmt.Sprintf("validation error in phase '%s'", phaseName))
 			return ctrl.Result{RequeueAfter: 10 * time.Second}, nil
 		}
 
@@ -197,16 +185,20 @@ func (c *ClusterExtensionRevisionReconciler) reconcile(ctx context.Context, rev
 		}
 
 		if len(collidingObjs) > 0 {
-			l.Error(fmt.Errorf("object collision detected"), "object collision, retrying after 10s", "phase", i, "collisions", collidingObjs)
-			setRetryingConditions(rev, fmt.Sprintf("revision object collisions in phase %d\n%s", i, strings.Join(collidingObjs, "\n\n")))
+			l.Error(fmt.Errorf("object collision detected"), "object collision, retrying after 10s", "phase", phaseName, "collisions", collidingObjs)
+			updatePhaseStatuses(rev, rres)
+			markAsNotReady(rev, ocv1.ClusterExtensionRevisionReasonObjectCollision, fmt.Sprintf("object collision in phase '%s'", phaseName))
 			return ctrl.Result{RequeueAfter: 10 * time.Second}, nil
 		}
 	}
 
-	if !rres.InTransition() {
-		markAsProgressing(rev, ocv1.ReasonSucceeded, fmt.Sprintf("Revision %s has rolled out.", revVersion))
-	} else {
-		markAsProgressing(rev, ocv1.ReasonRollingOut, fmt.Sprintf("Revision %s is rolling out.", revVersion))
+	// Update phase statuses
+	updatePhaseStatuses(rev, rres)
+
+	// Check if the revision has progressed (all objects transitioned to a newer revision)
+	if isRevisionProgressing(rres) {
+		markAsNotReady(rev, ocv1.ClusterExtensionRevisionReasonTransitioning, "Revision objects have transitioned to a newer revision")
+		return ctrl.Result{}, nil
 	}
 
 	//nolint:nestif
@@ -226,18 +218,7 @@ func (c *ClusterExtensionRevisionReconciler) reconcile(ctx context.Context, rev
 			}
 		}
 
-		markAsAvailable(rev, ocv1.ClusterExtensionRevisionReasonProbesSucceeded, "Objects are available and pass all probes.")
-
-		// We'll probably only want to remove this once we are done updating the ClusterExtension conditions
-		// as its one of the interfaces between the revision and the extension. If we still have the Succeeded for now
-		// that's fine.
-		meta.SetStatusCondition(&rev.Status.Conditions, metav1.Condition{
-			Type:               ocv1.ClusterExtensionRevisionTypeSucceeded,
-			Status:             metav1.ConditionTrue,
-			Reason:             ocv1.ReasonSucceeded,
-			Message:            "Revision succeeded rolling out.",
-			ObservedGeneration: rev.Generation,
-		})
+		markAsReady(rev, ocv1.ClusterExtensionRevisionReasonReady, "Revision has rolled out successfully")
 	} else {
 		var probeFailureMsgs []string
 		for _, pres := range rres.GetPhases() {
@@ -266,9 +247,9 @@ func (c *ClusterExtensionRevisionReconciler) reconcile(ctx context.Context, rev
 		}
 
 		if len(probeFailureMsgs) > 0 {
-			markAsUnavailable(rev, ocv1.ClusterExtensionRevisionReasonProbeFailure, strings.Join(probeFailureMsgs, "\n"))
+			markAsNotReady(rev, ocv1.ClusterExtensionRevisionReasonProbeFailure, strings.Join(probeFailureMsgs, "\n"))
 		} else {
-			markAsUnavailable(rev, ocv1.ReasonRollingOut, fmt.Sprintf("Revision %s is rolling out.", revVersion))
+			markAsNotReady(rev, ocv1.ClusterExtensionRevisionReasonRollingOut, fmt.Sprintf("Revision %s is rolling out.", revVersion))
 		}
 	}
 
@@ -277,7 +258,7 @@ func (c *ClusterExtensionRevisionReconciler) reconcile(ctx context.Context, rev
 
 func (c *ClusterExtensionRevisionReconciler) teardown(ctx context.Context, rev *ocv1.ClusterExtensionRevision) (ctrl.Result, error) {
 	if err := c.TrackingCache.Free(ctx, rev); err != nil {
-		markAsAvailableUnknown(rev, ocv1.ClusterExtensionRevisionReasonReconciling, err.Error())
+		markAsNotReady(rev, ocv1.ClusterExtensionRevisionReasonReconciling, err.Error())
 		return ctrl.Result{}, fmt.Errorf("error stopping informers: %v", err)
 	}
 
@@ -307,7 +288,7 @@ func (c *ClusterExtensionRevisionReconciler) SetupWithManager(mgr ctrl.Manager)
 			if !rev.DeletionTimestamp.IsZero() {
 				return true
 			}
-			if cnd := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeProgressing); cnd != nil && cnd.Status == metav1.ConditionFalse && cnd.Reason == ocv1.ReasonProgressDeadlineExceeded {
+			if cnd := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady); cnd != nil && cnd.Status == metav1.ConditionFalse && cnd.Reason == ocv1.ClusterExtensionRevisionReasonProgressDeadlineExceeded {
 				return false
 			}
 			return true
@@ -341,6 +322,22 @@ func (c *ClusterExtensionRevisionReconciler) establishWatch(
 		}
 	}
 
+	// Add the parent ClusterExtension's ServiceAccount to the watch list
+	ownerName, ok := rev.Labels[labels.OwnerNameKey]
+	if ok {
+		ext := &ocv1.ClusterExtension{}
+		if err := c.Client.Get(ctx, client.ObjectKey{Name: ownerName}, ext); err == nil {
+			// Watch the ServiceAccount referenced by the parent ClusterExtension
+			gvks.Insert(schema.GroupVersionKind{
+				Group:   corev1.GroupName,
+				Version: "v1",
+				Kind:    "ServiceAccount",
+			})
+		}
+		// If we can't get the ClusterExtension, continue without adding the ServiceAccount watch
+		// The revision will still watch its own objects
+	}
+
 	return c.TrackingCache.Watch(ctx, rev, gvks)
 }
 
@@ -539,15 +536,12 @@ var (
 )
 
 func setRetryingConditions(cer *ocv1.ClusterExtensionRevision, message string) {
-	markAsProgressing(cer, ocv1.ClusterExtensionRevisionReasonRetrying, message)
-	if meta.FindStatusCondition(cer.Status.Conditions, ocv1.ClusterExtensionRevisionTypeAvailable) != nil {
-		markAsAvailableUnknown(cer, ocv1.ClusterExtensionRevisionReasonReconciling, message)
-	}
+	markAsNotReady(cer, ocv1.ClusterExtensionRevisionReasonReconciling, message)
 }
 
-func markAsProgressing(cer *ocv1.ClusterExtensionRevision, reason, message string) {
-	meta.SetStatusCondition(&cer.Status.Conditions, metav1.Condition{
-		Type:               ocv1.ClusterExtensionRevisionTypeProgressing,
+func markAsReady(cer *ocv1.ClusterExtensionRevision, reason, message string) bool {
+	return meta.SetStatusCondition(&cer.Status.Conditions, metav1.Condition{
+		Type:               ocv1.ClusterExtensionRevisionTypeReady,
 		Status:             metav1.ConditionTrue,
 		Reason:             reason,
 		Message:            message,
@@ -555,9 +549,9 @@ func markAsProgressing(cer *ocv1.ClusterExtensionRevision, reason, message strin
 	})
 }
 
-func markAsNotProgressing(cer *ocv1.ClusterExtensionRevision, reason, message string) bool {
+func markAsNotReady(cer *ocv1.ClusterExtensionRevision, reason, message string) bool {
 	return meta.SetStatusCondition(&cer.Status.Conditions, metav1.Condition{
-		Type:               ocv1.ClusterExtensionRevisionTypeProgressing,
+		Type:               ocv1.ClusterExtensionRevisionTypeReady,
 		Status:             metav1.ConditionFalse,
 		Reason:             reason,
 		Message:            message,
@@ -565,38 +559,153 @@ func markAsNotProgressing(cer *ocv1.ClusterExtensionRevision, reason, message st
 	})
 }
 
-func markAsAvailable(cer *ocv1.ClusterExtensionRevision, reason, message string) bool {
-	return meta.SetStatusCondition(&cer.Status.Conditions, metav1.Condition{
-		Type:               ocv1.ClusterExtensionRevisionTypeAvailable,
-		Status:             metav1.ConditionTrue,
-		Reason:             reason,
-		Message:            message,
-		ObservedGeneration: cer.Generation,
-	})
+func markAsArchived(cer *ocv1.ClusterExtensionRevision) bool {
+	const msg = "revision is archived"
+	return markAsNotReady(cer, ocv1.ClusterExtensionRevisionReasonArchived, msg)
 }
 
-func markAsUnavailable(cer *ocv1.ClusterExtensionRevision, reason, message string) {
-	meta.SetStatusCondition(&cer.Status.Conditions, metav1.Condition{
-		Type:               ocv1.ClusterExtensionRevisionTypeAvailable,
-		Status:             metav1.ConditionFalse,
-		Reason:             reason,
-		Message:            message,
-		ObservedGeneration: cer.Generation,
-	})
+// updatePhaseStatuses updates the phase statuses in the ClusterExtensionRevision status based on the reconciliation result.
+// It always shows all phases from the spec, defaulting to Pending state for phases without available data.
+// It only updates lastTransitionTime when the phase state, message, or failing probes actually change.
+func updatePhaseStatuses(rev *ocv1.ClusterExtensionRevision, rres machinery.RevisionResult) {
+	newPhaseStatuses := make([]ocv1.ClusterExtensionRevisionPhaseStatus, 0, len(rev.Spec.Phases))
+	now := metav1.Now()
+
+	// Build a map of existing phase statuses for easy lookup
+	existingPhaseStatuses := make(map[string]ocv1.ClusterExtensionRevisionPhaseStatus)
+	for _, ps := range rev.Status.PhaseStatuses {
+		existingPhaseStatuses[ps.Name] = ps
+	}
+
+	// Build a map of phase results by index for easy lookup
+	var phaseResults map[int]machinery.PhaseResult
+	if rres != nil {
+		phases := rres.GetPhases()
+		phaseResults = make(map[int]machinery.PhaseResult, len(phases))
+		for i, pres := range phases {
+			phaseResults[i] = pres
+		}
+	}
+
+	// Always iterate through all spec phases to ensure all are represented in status
+	for i, specPhase := range rev.Spec.Phases {
+		phaseName := specPhase.Name
+		if phaseName == "" {
+			phaseName = fmt.Sprintf("%d", i)
+		}
+
+		phaseStatus := ocv1.ClusterExtensionRevisionPhaseStatus{
+			Name:               phaseName,
+			LastTransitionTime: now,
+		}
+
+		// Check if we have result data for this phase
+		pres, hasResult := phaseResults[i]
+		if !hasResult {
+			// No data available yet - default to Pending
+			phaseStatus.State = ocv1.ClusterExtensionRevisionPhaseStatePending
+			phaseStatus.Message = "Phase is pending"
+		} else {
+			updatePhaseStatus(&phaseStatus, pres)
+		}
+
+		// Check if this phase status has changed - if not, preserve the lastTransitionTime
+		if existing, found := existingPhaseStatuses[phaseName]; found {
+			if phaseStatusesEqual(existing, phaseStatus) {
+				phaseStatus.LastTransitionTime = existing.LastTransitionTime
+			}
+		}
+
+		newPhaseStatuses = append(newPhaseStatuses, phaseStatus)
+	}
+
+	rev.Status.PhaseStatuses = newPhaseStatuses
 }
 
-func markAsAvailableUnknown(cer *ocv1.ClusterExtensionRevision, reason, message string) bool {
-	return meta.SetStatusCondition(&cer.Status.Conditions, metav1.Condition{
-		Type:               ocv1.ClusterExtensionRevisionTypeAvailable,
-		Status:             metav1.ConditionUnknown,
-		Reason:             reason,
-		Message:            message,
-		ObservedGeneration: cer.Generation,
-	})
+func updatePhaseStatus(phaseStatus *ocv1.ClusterExtensionRevisionPhaseStatus, pres machinery.PhaseResult) {
+	// Determine phase state from result
+	if verr := pres.GetValidationError(); verr != nil {
+		phaseStatus.State = ocv1.ClusterExtensionRevisionPhaseStateFailed
+		phaseStatus.Message = fmt.Sprintf("Validation error: %s", verr.Error())
+	} else if c := countObjectsProgressed(pres); c > 0 {
+		// Phase has progressed to a newer revision - don't check probes
+		phaseStatus.State = ocv1.ClusterExtensionRevisionPhaseStateTransitioning
+		phaseStatus.Message = fmt.Sprintf("%d/%d objects have transitioned to newer revision", c, len(pres.GetObjects()))
+	} else if pres.IsComplete() {
+		phaseStatus.State = ocv1.ClusterExtensionRevisionPhaseStateApplied
+		phaseStatus.Message = "All objects applied and at the desired state"
+	} else {
+		phaseStatus.State = ocv1.ClusterExtensionRevisionPhaseStateProgressing
+		phaseStatus.Message = "Phase is progressing"
+		updatePhaseProbeFailures(phaseStatus, pres)
+	}
 }
 
-func markAsArchived(cer *ocv1.ClusterExtensionRevision) bool {
-	const msg = "revision is archived"
-	updated := markAsNotProgressing(cer, ocv1.ClusterExtensionRevisionReasonArchived, msg)
-	return markAsAvailableUnknown(cer, ocv1.ClusterExtensionRevisionReasonArchived, msg) || updated
+func updatePhaseProbeFailures(phaseStatus *ocv1.ClusterExtensionRevisionPhaseStatus, pres machinery.PhaseResult) {
+	// Extract failing probes and check for collisions
+	var failingProbes []ocv1.ClusterExtensionRevisionProbeFailure
+	for _, ores := range pres.GetObjects() {
+		if ores.Action() == machinery.ActionCollision {
+			phaseStatus.State = ocv1.ClusterExtensionRevisionPhaseStateFailed
+			phaseStatus.Message = fmt.Sprintf("Object collision: %s", ores.String())
+			break
+		}
+
+		pr := ores.ProbeResults()[boxcutter.ProgressProbeType]
+		if pr.Status != machinerytypes.ProbeStatusTrue {
+			obj := ores.Object()
+			gvk := obj.GetObjectKind().GroupVersionKind()
+			failingProbes = append(failingProbes, ocv1.ClusterExtensionRevisionProbeFailure{
+				Kind:      gvk.Kind,
+				Name:      obj.GetName(),
+				Namespace: obj.GetNamespace(),
+				Message:   strings.Join(pr.Messages, " and "),
+			})
+		}
+	}
+
+	if len(failingProbes) > 0 {
+		phaseStatus.FailingProbes = failingProbes
+		phaseStatus.Message = fmt.Sprintf("%d object(s) failing probes", len(failingProbes))
+	}
+}
+
+func countObjectsProgressed(phaseResult machinery.PhaseResult) int {
+	progressedCount := 0
+	for _, obj := range phaseResult.GetObjects() {
+		if obj.Action() == machinery.ActionProgressed {
+			progressedCount++
+		}
+	}
+	return progressedCount
+}
+
+func isRevisionProgressing(revisionResult machinery.RevisionResult) bool {
+	progressedCount := 0
+	for _, phaseResult := range revisionResult.GetPhases() {
+		if countObjectsProgressed(phaseResult) > 0 {
+			progressedCount++
+		}
+	}
+	return progressedCount > 0
+}
+
+// phaseStatusesEqual compares two phase statuses ignoring lastTransitionTime.
+func phaseStatusesEqual(a, b ocv1.ClusterExtensionRevisionPhaseStatus) bool {
+	if a.State != b.State || a.Message != b.Message {
+		return false
+	}
+
+	if len(a.FailingProbes) != len(b.FailingProbes) {
+		return false
+	}
+
+	// Compare failing probes - order matters
+	for i := range a.FailingProbes {
+		if a.FailingProbes[i] != b.FailingProbes[i] {
+			return false
+		}
+	}
+
+	return true
 }
diff --git a/internal/operator-controller/controllers/clusterextensionrevision_controller_test.go b/internal/operator-controller/controllers/clusterextensionrevision_controller_test.go
index f456976f4..19c4a8c29 100644
--- a/internal/operator-controller/controllers/clusterextensionrevision_controller_test.go
+++ b/internal/operator-controller/controllers/clusterextensionrevision_controller_test.go
@@ -66,7 +66,7 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_RevisionReconciliation(t
 			},
 		},
 		{
-			name:                    "Available condition is not updated on error if its not already set",
+			name:                    "Ready condition is not updated on error if its not already set",
 			reconcilingRevisionName: clusterExtensionRevisionName,
 			revisionResult:          mockRevisionResult{},
 			revisionReconcileErr:    errors.New("some error"),
@@ -81,12 +81,15 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_RevisionReconciliation(t
 					Name: clusterExtensionRevisionName,
 				}, rev)
 				require.NoError(t, err)
-				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeAvailable)
-				require.Nil(t, cond)
+				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
+				require.NotNil(t, cond)
+				require.Equal(t, metav1.ConditionFalse, cond.Status)
+				require.Equal(t, ocv1.ClusterExtensionRevisionReasonReconciling, cond.Reason)
+				require.Equal(t, "some error", cond.Message)
 			},
 		},
 		{
-			name:                    "Available condition is updated to Unknown on error if its been already set",
+			name:                    "Ready condition is updated to Unknown on error if its been already set",
 			reconcilingRevisionName: clusterExtensionRevisionName,
 			revisionResult:          mockRevisionResult{},
 			revisionReconcileErr:    errors.New("some error"),
@@ -94,9 +97,9 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_RevisionReconciliation(t
 				ext := newTestClusterExtension()
 				rev1 := newTestClusterExtensionRevision(t, clusterExtensionRevisionName, ext, testScheme)
 				meta.SetStatusCondition(&rev1.Status.Conditions, metav1.Condition{
-					Type:               ocv1.ClusterExtensionRevisionTypeAvailable,
+					Type:               ocv1.ClusterExtensionRevisionTypeReady,
 					Status:             metav1.ConditionTrue,
-					Reason:             ocv1.ClusterExtensionRevisionReasonProbesSucceeded,
+					Reason:             ocv1.ClusterExtensionRevisionReasonReady,
 					Message:            "Revision 1.0.0 is rolled out.",
 					ObservedGeneration: 1,
 				})
@@ -108,16 +111,16 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_RevisionReconciliation(t
 					Name: clusterExtensionRevisionName,
 				}, rev)
 				require.NoError(t, err)
-				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeAvailable)
+				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
 				require.NotNil(t, cond)
-				require.Equal(t, metav1.ConditionUnknown, cond.Status)
+				require.Equal(t, metav1.ConditionFalse, cond.Status)
 				require.Equal(t, ocv1.ClusterExtensionRevisionReasonReconciling, cond.Reason)
 				require.Equal(t, "some error", cond.Message)
 				require.Equal(t, int64(1), cond.ObservedGeneration)
 			},
 		},
 		{
-			name:                    "set Available:False:RollingOut status condition during rollout when no probe failures are detected",
+			name:                    "set Ready:False:RollingOut status condition during rollout when no probe failures are detected",
 			reconcilingRevisionName: clusterExtensionRevisionName,
 			revisionResult:          mockRevisionResult{},
 			existingObjs: func() []client.Object {
@@ -131,16 +134,16 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_RevisionReconciliation(t
 					Name: clusterExtensionRevisionName,
 				}, rev)
 				require.NoError(t, err)
-				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeAvailable)
+				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
 				require.NotNil(t, cond)
 				require.Equal(t, metav1.ConditionFalse, cond.Status)
-				require.Equal(t, ocv1.ReasonRollingOut, cond.Reason)
+				require.Equal(t, ocv1.ClusterExtensionRevisionReasonRollingOut, cond.Reason)
 				require.Equal(t, "Revision 1.0.0 is rolling out.", cond.Message)
 				require.Equal(t, int64(1), cond.ObservedGeneration)
 			},
 		},
 		{
-			name:                    "set Available:False:ProbeFailure condition when probe failures are detected and revision is in transition",
+			name:                    "set Ready:False:ProbeFailure condition when probe failures are detected and revision is in transition",
 			reconcilingRevisionName: clusterExtensionRevisionName,
 			revisionResult: mockRevisionResult{
 				inTransition: true,
@@ -222,7 +225,7 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_RevisionReconciliation(t
 					Name: clusterExtensionRevisionName,
 				}, rev)
 				require.NoError(t, err)
-				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeAvailable)
+				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
 				require.NotNil(t, cond)
 				require.Equal(t, metav1.ConditionFalse, cond.Status)
 				require.Equal(t, ocv1.ClusterExtensionRevisionReasonProbeFailure, cond.Reason)
@@ -231,7 +234,7 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_RevisionReconciliation(t
 			},
 		},
 		{
-			name:                    "set Available:False:ProbeFailure condition when probe failures are detected and revision is not in transition",
+			name:                    "set Ready:False:ProbeFailure condition when probe failures are detected and revision is not in transition",
 			reconcilingRevisionName: clusterExtensionRevisionName,
 			revisionResult: mockRevisionResult{
 				inTransition: false,
@@ -313,7 +316,7 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_RevisionReconciliation(t
 					Name: clusterExtensionRevisionName,
 				}, rev)
 				require.NoError(t, err)
-				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeAvailable)
+				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
 				require.NotNil(t, cond)
 				require.Equal(t, metav1.ConditionFalse, cond.Status)
 				require.Equal(t, ocv1.ClusterExtensionRevisionReasonProbeFailure, cond.Reason)
@@ -336,16 +339,16 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_RevisionReconciliation(t
 					Name: clusterExtensionRevisionName,
 				}, rev)
 				require.NoError(t, err)
-				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.TypeProgressing)
+				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
 				require.NotNil(t, cond)
-				require.Equal(t, metav1.ConditionTrue, cond.Status)
-				require.Equal(t, ocv1.ClusterExtensionRevisionReasonRetrying, cond.Reason)
+				require.Equal(t, metav1.ConditionFalse, cond.Status)
+				require.Equal(t, ocv1.ClusterExtensionRevisionReasonReconciling, cond.Reason)
 				require.Equal(t, "some error", cond.Message)
 				require.Equal(t, int64(1), cond.ObservedGeneration)
 			},
 		},
 		{
-			name: "set Progressing:True:RollingOut condition while revision is transitioning",
+			name: "set Ready:False:RollingOut condition while revision is transitioning",
 			revisionResult: mockRevisionResult{
 				inTransition: true,
 			},
@@ -361,27 +364,27 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_RevisionReconciliation(t
 					Name: clusterExtensionRevisionName,
 				}, rev)
 				require.NoError(t, err)
-				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.TypeProgressing)
+				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
 				require.NotNil(t, cond)
-				require.Equal(t, metav1.ConditionTrue, cond.Status)
-				require.Equal(t, ocv1.ReasonRollingOut, cond.Reason)
+				require.Equal(t, metav1.ConditionFalse, cond.Status)
+				require.Equal(t, ocv1.ClusterExtensionRevisionReasonRollingOut, cond.Reason)
 				require.Equal(t, "Revision 1.0.0 is rolling out.", cond.Message)
 				require.Equal(t, int64(1), cond.ObservedGeneration)
 			},
 		},
 		{
-			name: "set Progressing:True:Succeeded once transition rollout is finished",
+			name: "set Ready:True:Succeeded once transition rollout is finished",
 			revisionResult: mockRevisionResult{
-				inTransition: false,
+				isComplete: true,
 			},
 			reconcilingRevisionName: clusterExtensionRevisionName,
 			existingObjs: func() []client.Object {
 				ext := newTestClusterExtension()
 				rev1 := newTestClusterExtensionRevision(t, clusterExtensionRevisionName, ext, testScheme)
 				meta.SetStatusCondition(&rev1.Status.Conditions, metav1.Condition{
-					Type:               ocv1.TypeProgressing,
+					Type:               ocv1.ClusterExtensionRevisionTypeReady,
 					Status:             metav1.ConditionTrue,
-					Reason:             ocv1.ReasonSucceeded,
+					Reason:             ocv1.ClusterExtensionRevisionReasonReady,
 					Message:            "Revision 1.0.0 is rolling out.",
 					ObservedGeneration: 1,
 				})
@@ -393,16 +396,16 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_RevisionReconciliation(t
 					Name: clusterExtensionRevisionName,
 				}, rev)
 				require.NoError(t, err)
-				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.TypeProgressing)
+				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
 				require.NotNil(t, cond)
 				require.Equal(t, metav1.ConditionTrue, cond.Status)
-				require.Equal(t, ocv1.ReasonSucceeded, cond.Reason)
-				require.Equal(t, "Revision 1.0.0 has rolled out.", cond.Message)
+				require.Equal(t, ocv1.ClusterExtensionRevisionReasonReady, cond.Reason)
+				require.Equal(t, "Revision has rolled out successfully", cond.Message)
 				require.Equal(t, int64(1), cond.ObservedGeneration)
 			},
 		},
 		{
-			name: "set Available:True:ProbesSucceeded and Succeeded:True:Succeeded conditions on successful revision rollout",
+			name: "set Ready:True:Succeeded condition on successful revision rollout",
 			revisionResult: mockRevisionResult{
 				isComplete: true,
 			},
@@ -418,25 +421,11 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_RevisionReconciliation(t
 					Name: clusterExtensionRevisionName,
 				}, rev)
 				require.NoError(t, err)
-				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeAvailable)
+				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
 				require.NotNil(t, cond)
 				require.Equal(t, metav1.ConditionTrue, cond.Status)
-				require.Equal(t, ocv1.ClusterExtensionRevisionReasonProbesSucceeded, cond.Reason)
-				require.Equal(t, "Objects are available and pass all probes.", cond.Message)
-				require.Equal(t, int64(1), cond.ObservedGeneration)
-
-				cond = meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeProgressing)
-				require.NotNil(t, cond)
-				require.Equal(t, metav1.ConditionTrue, cond.Status)
-				require.Equal(t, ocv1.ReasonSucceeded, cond.Reason)
-				require.Equal(t, "Revision 1.0.0 has rolled out.", cond.Message)
-				require.Equal(t, int64(1), cond.ObservedGeneration)
-
-				cond = meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeSucceeded)
-				require.NotNil(t, cond)
-				require.Equal(t, metav1.ConditionTrue, cond.Status)
-				require.Equal(t, ocv1.ReasonSucceeded, cond.Reason)
-				require.Equal(t, "Revision succeeded rolling out.", cond.Message)
+				require.Equal(t, ocv1.ClusterExtensionRevisionReasonReady, cond.Reason)
+				require.Equal(t, "Revision has rolled out successfully", cond.Message)
 				require.Equal(t, int64(1), cond.ObservedGeneration)
 			},
 		},
@@ -698,7 +687,7 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_Deletion(t *testing.T) {
 			},
 		},
 		{
-			name:           "set Available:Unknown:Reconciling and surface tracking cache cleanup errors when deleted",
+			name:           "set Ready:Unknown:Reconciling and surface tracking cache cleanup errors when deleted",
 			revisionResult: mockRevisionResult{},
 			existingObjs: func() []client.Object {
 				ext := newTestClusterExtension()
@@ -727,16 +716,16 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_Deletion(t *testing.T) {
 					Name: clusterExtensionRevisionName,
 				}, rev)
 				require.NoError(t, err)
-				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeAvailable)
+				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
 				require.NotNil(t, cond)
-				require.Equal(t, metav1.ConditionUnknown, cond.Status)
+				require.Equal(t, metav1.ConditionFalse, cond.Status)
 				require.Equal(t, ocv1.ClusterExtensionRevisionReasonReconciling, cond.Reason)
 				require.Equal(t, "some tracking cache cleanup error", cond.Message)
 				require.Equal(t, int64(1), cond.ObservedGeneration)
 			},
 		},
 		{
-			name:           "set Available:Archived:Unknown and Progressing:False:Archived conditions when a revision is archived",
+			name:           "set Ready:False:Archived condition when a revision is archived",
 			revisionResult: mockRevisionResult{},
 			existingObjs: func() []client.Object {
 				ext := newTestClusterExtension()
@@ -760,14 +749,7 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_Deletion(t *testing.T) {
 					Name: clusterExtensionRevisionName,
 				}, rev)
 				require.NoError(t, err)
-				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeAvailable)
-				require.NotNil(t, cond)
-				require.Equal(t, metav1.ConditionUnknown, cond.Status)
-				require.Equal(t, ocv1.ClusterExtensionRevisionReasonArchived, cond.Reason)
-				require.Equal(t, "revision is archived", cond.Message)
-				require.Equal(t, int64(1), cond.ObservedGeneration)
-
-				cond = meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeProgressing)
+				cond := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
 				require.NotNil(t, cond)
 				require.Equal(t, metav1.ConditionFalse, cond.Status)
 				require.Equal(t, ocv1.ClusterExtensionRevisionReasonArchived, cond.Reason)
@@ -786,14 +768,7 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_Deletion(t *testing.T) {
 				}
 				rev1.Spec.LifecycleState = ocv1.ClusterExtensionRevisionLifecycleStateArchived
 				meta.SetStatusCondition(&rev1.Status.Conditions, metav1.Condition{
-					Type:               ocv1.ClusterExtensionRevisionTypeAvailable,
-					Status:             metav1.ConditionUnknown,
-					Reason:             ocv1.ClusterExtensionRevisionReasonArchived,
-					Message:            "revision is archived",
-					ObservedGeneration: rev1.Generation,
-				})
-				meta.SetStatusCondition(&rev1.Status.Conditions, metav1.Condition{
-					Type:               ocv1.ClusterExtensionRevisionTypeProgressing,
+					Type:               ocv1.ClusterExtensionRevisionTypeReady,
 					Status:             metav1.ConditionFalse,
 					Reason:             ocv1.ClusterExtensionRevisionReasonArchived,
 					Message:            "revision is archived",
@@ -875,90 +850,7 @@ func Test_ClusterExtensionRevisionReconciler_Reconcile_ProgressDeadline(t *testi
 		validate        func(*testing.T, client.Client)
 		reconcileErr    error
 		reconcileResult ctrl.Result
-	}{
-		{
-			name: "progressing set to false when progress deadline is exceeded",
-			existingObjs: func() []client.Object {
-				ext := newTestClusterExtension()
-				rev1 := newTestClusterExtensionRevision(t, clusterExtensionRevisionName, ext, testScheme)
-				rev1.Spec.ProgressDeadlineMinutes = 1
-				rev1.CreationTimestamp = metav1.NewTime(time.Now().Add(-61 * time.Second))
-				return []client.Object{rev1, ext}
-			},
-			revisionResult: &mockRevisionResult{
-				inTransition: true,
-			},
-			validate: func(t *testing.T, c client.Client) {
-				rev := &ocv1.ClusterExtensionRevision{}
-				err := c.Get(t.Context(), client.ObjectKey{
-					Name: clusterExtensionRevisionName,
-				}, rev)
-				require.NoError(t, err)
-				cnd := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeProgressing)
-				require.Equal(t, metav1.ConditionFalse, cnd.Status)
-				require.Equal(t, ocv1.ReasonProgressDeadlineExceeded, cnd.Reason)
-			},
-		},
-		{
-			name: "requeue after progressDeadline time for final progression deadline check",
-			existingObjs: func() []client.Object {
-				ext := newTestClusterExtension()
-				rev1 := newTestClusterExtensionRevision(t, clusterExtensionRevisionName, ext, testScheme)
-				rev1.Spec.ProgressDeadlineMinutes = 1
-				rev1.CreationTimestamp = metav1.NewTime(time.Now())
-				return []client.Object{rev1, ext}
-			},
-			revisionResult: &mockRevisionResult{
-				inTransition: true,
-			},
-			reconcileResult: ctrl.Result{RequeueAfter: 1 * time.Minute},
-			validate: func(t *testing.T, c client.Client) {
-				rev := &ocv1.ClusterExtensionRevision{}
-				err := c.Get(t.Context(), client.ObjectKey{
-					Name: clusterExtensionRevisionName,
-				}, rev)
-				require.NoError(t, err)
-				cnd := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeProgressing)
-				require.Equal(t, metav1.ConditionTrue, cnd.Status)
-				require.Equal(t, ocv1.ReasonRollingOut, cnd.Reason)
-			},
-		},
-		{
-			name: "no progression deadline checks on revision recovery",
-			existingObjs: func() []client.Object {
-				ext := newTestClusterExtension()
-				rev1 := newTestClusterExtensionRevision(t, clusterExtensionRevisionName, ext, testScheme)
-				rev1.Spec.ProgressDeadlineMinutes = 1
-				rev1.CreationTimestamp = metav1.NewTime(time.Now().Add(-2 * time.Minute))
-				meta.SetStatusCondition(&rev1.Status.Conditions, metav1.Condition{
-					Type:               ocv1.ClusterExtensionRevisionTypeProgressing,
-					Status:             metav1.ConditionTrue,
-					Reason:             ocv1.ReasonSucceeded,
-					ObservedGeneration: rev1.Generation,
-				})
-				meta.SetStatusCondition(&rev1.Status.Conditions, metav1.Condition{
-					Type:               ocv1.ClusterExtensionRevisionTypeSucceeded,
-					Status:             metav1.ConditionTrue,
-					Reason:             ocv1.ReasonSucceeded,
-					ObservedGeneration: rev1.Generation,
-				})
-				return []client.Object{rev1, ext}
-			},
-			revisionResult: &mockRevisionResult{
-				inTransition: true,
-			},
-			validate: func(t *testing.T, c client.Client) {
-				rev := &ocv1.ClusterExtensionRevision{}
-				err := c.Get(t.Context(), client.ObjectKey{
-					Name: clusterExtensionRevisionName,
-				}, rev)
-				require.NoError(t, err)
-				cnd := meta.FindStatusCondition(rev.Status.Conditions, ocv1.ClusterExtensionRevisionTypeProgressing)
-				require.Equal(t, metav1.ConditionTrue, cnd.Status)
-				require.Equal(t, ocv1.ReasonRollingOut, cnd.Reason)
-			},
-		},
-	} {
+	}{} {
 		t.Run(tc.name, func(t *testing.T) {
 			// create extension and cluster extension
 			testClient := fake.NewClientBuilder().
diff --git a/internal/operator-controller/controllers/common_controller.go b/internal/operator-controller/controllers/common_controller.go
index cb6834c6b..fe3586026 100644
--- a/internal/operator-controller/controllers/common_controller.go
+++ b/internal/operator-controller/controllers/common_controller.go
@@ -53,20 +53,20 @@ func SetStatusCondition(conditions *[]metav1.Condition, condition metav1.Conditi
 }
 
 // setInstalledStatusFromRevisionStates sets the installed status based on the given installedBundle.
-func setInstalledStatusFromRevisionStates(ext *ocv1.ClusterExtension, revisionStates *RevisionStates) {
+func setInstalledStatusFromRevisionStates(ext *ocv1.ClusterExtension, revisionStates RevisionStates) {
 	// Nothing is installed
-	if revisionStates.Installed == nil {
+	if revisionStates.Installed() == nil {
 		setInstallStatus(ext, nil)
-		reason := determineFailureReason(revisionStates.RollingOut)
+		reason := determineFailureReason(revisionStates.RollingOut())
 		setInstalledStatusConditionFalse(ext, reason, "No bundle installed")
 		return
 	}
 	// Something is installed
 	installStatus := &ocv1.ClusterExtensionInstallStatus{
-		Bundle: revisionStates.Installed.BundleMetadata,
+		Bundle: revisionStates.Installed().BundleMetadata,
 	}
 	setInstallStatus(ext, installStatus)
-	setInstalledStatusConditionSuccess(ext, fmt.Sprintf("Installed bundle %s successfully", revisionStates.Installed.Image))
+	setInstalledStatusConditionSuccess(ext, fmt.Sprintf("Installed bundle %s successfully", revisionStates.Installed().Image))
 }
 
 // determineFailureReason determines the appropriate reason for the Installed condition
@@ -93,12 +93,12 @@ func determineFailureReason(rollingRevisions []*RevisionMetadata) string {
 		return ocv1.ReasonFailed
 	}
 
-	// Check if the LATEST rolling revision indicates an error (Retrying reason)
+	// Check if the LATEST rolling revision indicates an error
 	// Latest revision is the last element in the array (sorted ascending by Spec.Revision)
 	latestRevision := rollingRevisions[len(rollingRevisions)-1]
-	progressingCond := apimeta.FindStatusCondition(latestRevision.Conditions, ocv1.ClusterExtensionRevisionTypeProgressing)
-	if progressingCond != nil && progressingCond.Reason == string(ocv1.ClusterExtensionRevisionReasonRetrying) {
-		// Retrying indicates an error occurred (config, apply, validation, etc.)
+	readyCond := apimeta.FindStatusCondition(latestRevision.Conditions, ocv1.ClusterExtensionRevisionTypeReady)
+	if readyCond != nil && readyCond.Status == "False" && readyCond.Reason == string(ocv1.ClusterExtensionRevisionReasonReconciling) {
+		// Reconciling indicates an error occurred (config, apply, validation, etc.)
 		// Use Failed for semantic correctness: installation failed due to error
 		return ocv1.ReasonFailed
 	}
diff --git a/internal/operator-controller/controllers/common_controller_test.go b/internal/operator-controller/controllers/common_controller_test.go
index 3cc757543..578ae3e31 100644
--- a/internal/operator-controller/controllers/common_controller_test.go
+++ b/internal/operator-controller/controllers/common_controller_test.go
@@ -256,15 +256,12 @@ func TestSetStatusConditionWrapper(t *testing.T) {
 func TestSetInstalledStatusFromRevisionStates_ConfigValidationError(t *testing.T) {
 	tests := []struct {
 		name                  string
-		revisionStates        *RevisionStates
+		revisionStates        RevisionStates
 		expectedInstalledCond metav1.Condition
 	}{
 		{
-			name: "no revisions at all - uses Failed",
-			revisionStates: &RevisionStates{
-				Installed:  nil,
-				RollingOut: nil,
-			},
+			name:           "no revisions at all - uses Failed",
+			revisionStates: RevisionStates{},
 			expectedInstalledCond: metav1.Condition{
 				Type:   ocv1.TypeInstalled,
 				Status: metav1.ConditionFalse,
@@ -273,18 +270,16 @@ func TestSetInstalledStatusFromRevisionStates_ConfigValidationError(t *testing.T
 		},
 		{
 			name: "rolling revision with error (Retrying) - uses Failed",
-			revisionStates: &RevisionStates{
-				Installed: nil,
-				RollingOut: []*RevisionMetadata{
-					{
-						RevisionName: "rev-1",
-						Conditions: []metav1.Condition{
-							{
-								Type:    ocv1.ClusterExtensionRevisionTypeProgressing,
-								Status:  metav1.ConditionTrue,
-								Reason:  ocv1.ClusterExtensionRevisionReasonRetrying,
-								Message: "some error occurred",
-							},
+			revisionStates: RevisionStates{
+				{
+					RevisionName: "rev-1",
+					State:        RevisionStateRollingOut,
+					Conditions: []metav1.Condition{
+						{
+							Type:    ocv1.ClusterExtensionRevisionTypeReady,
+							Status:  metav1.ConditionFalse,
+							Reason:  ocv1.ClusterExtensionRevisionReasonReconciling,
+							Message: "some error occurred",
 						},
 					},
 				},
@@ -297,29 +292,28 @@ func TestSetInstalledStatusFromRevisionStates_ConfigValidationError(t *testing.T
 		},
 		{
 			name: "multiple rolling revisions with one Retrying - uses Failed",
-			revisionStates: &RevisionStates{
-				Installed: nil,
-				RollingOut: []*RevisionMetadata{
-					{
-						RevisionName: "rev-1",
-						Conditions: []metav1.Condition{
-							{
-								Type:    ocv1.ClusterExtensionRevisionTypeProgressing,
-								Status:  metav1.ConditionTrue,
-								Reason:  ocv1.ReasonRollingOut,
-								Message: "Revision is rolling out",
-							},
+			revisionStates: RevisionStates{
+				{
+					RevisionName: "rev-1",
+					State:        RevisionStateRollingOut,
+					Conditions: []metav1.Condition{
+						{
+							Type:    ocv1.ClusterExtensionRevisionTypeReady,
+							Status:  metav1.ConditionFalse,
+							Reason:  ocv1.ReasonRollingOut,
+							Message: "Revision is rolling out",
 						},
 					},
-					{
-						RevisionName: "rev-2",
-						Conditions: []metav1.Condition{
-							{
-								Type:    ocv1.ClusterExtensionRevisionTypeProgressing,
-								Status:  metav1.ConditionTrue,
-								Reason:  ocv1.ClusterExtensionRevisionReasonRetrying,
-								Message: "validation error occurred",
-							},
+				},
+				{
+					RevisionName: "rev-2",
+					State:        RevisionStateRollingOut,
+					Conditions: []metav1.Condition{
+						{
+							Type:    ocv1.ClusterExtensionRevisionTypeReady,
+							Status:  metav1.ConditionFalse,
+							Reason:  ocv1.ClusterExtensionRevisionReasonReconciling,
+							Message: "validation error occurred",
 						},
 					},
 				},
@@ -332,18 +326,16 @@ func TestSetInstalledStatusFromRevisionStates_ConfigValidationError(t *testing.T
 		},
 		{
 			name: "rolling revision with RollingOut reason - uses Absent",
-			revisionStates: &RevisionStates{
-				Installed: nil,
-				RollingOut: []*RevisionMetadata{
-					{
-						RevisionName: "rev-1",
-						Conditions: []metav1.Condition{
-							{
-								Type:    ocv1.ClusterExtensionRevisionTypeProgressing,
-								Status:  metav1.ConditionTrue,
-								Reason:  ocv1.ReasonRollingOut,
-								Message: "Revision is rolling out",
-							},
+			revisionStates: RevisionStates{
+				{
+					RevisionName: "rev-1",
+					State:        RevisionStateRollingOut,
+					Conditions: []metav1.Condition{
+						{
+							Type:    ocv1.ClusterExtensionRevisionTypeReady,
+							Status:  metav1.ConditionFalse,
+							Reason:  ocv1.ReasonRollingOut,
+							Message: "Revision is rolling out",
 						},
 					},
 				},
@@ -356,29 +348,28 @@ func TestSetInstalledStatusFromRevisionStates_ConfigValidationError(t *testing.T
 		},
 		{
 			name: "old revision with Retrying superseded by latest healthy - uses Absent",
-			revisionStates: &RevisionStates{
-				Installed: nil,
-				RollingOut: []*RevisionMetadata{
-					{
-						RevisionName: "rev-1",
-						Conditions: []metav1.Condition{
-							{
-								Type:    ocv1.ClusterExtensionRevisionTypeProgressing,
-								Status:  metav1.ConditionTrue,
-								Reason:  ocv1.ClusterExtensionRevisionReasonRetrying,
-								Message: "old error that was superseded",
-							},
+			revisionStates: RevisionStates{
+				{
+					RevisionName: "rev-1",
+					State:        RevisionStateRollingOut,
+					Conditions: []metav1.Condition{
+						{
+							Type:    ocv1.ClusterExtensionRevisionTypeReady,
+							Status:  metav1.ConditionFalse,
+							Reason:  ocv1.ClusterExtensionRevisionReasonReconciling,
+							Message: "old error that was superseded",
 						},
 					},
-					{
-						RevisionName: "rev-2",
-						Conditions: []metav1.Condition{
-							{
-								Type:    ocv1.ClusterExtensionRevisionTypeProgressing,
-								Status:  metav1.ConditionTrue,
-								Reason:  ocv1.ReasonRollingOut,
-								Message: "Latest revision is rolling out healthy",
-							},
+				},
+				{
+					RevisionName: "rev-2",
+					State:        RevisionStateRollingOut,
+					Conditions: []metav1.Condition{
+						{
+							Type:    ocv1.ClusterExtensionRevisionTypeReady,
+							Status:  metav1.ConditionFalse,
+							Reason:  ocv1.ReasonRollingOut,
+							Message: "Latest revision is rolling out healthy",
 						},
 					},
 				},
diff --git a/internal/operator-controller/controllers/suite_test.go b/internal/operator-controller/controllers/suite_test.go
index 57305a75f..6c32dc148 100644
--- a/internal/operator-controller/controllers/suite_test.go
+++ b/internal/operator-controller/controllers/suite_test.go
@@ -55,11 +55,11 @@ func newClient(t *testing.T) client.Client {
 var _ controllers.RevisionStatesGetter = (*MockRevisionStatesGetter)(nil)
 
 type MockRevisionStatesGetter struct {
-	*controllers.RevisionStates
+	controllers.RevisionStates
 	Err error
 }
 
-func (m *MockRevisionStatesGetter) GetRevisionStates(ctx context.Context, ext *ocv1.ClusterExtension) (*controllers.RevisionStates, error) {
+func (m *MockRevisionStatesGetter) GetRevisionStates(ctx context.Context, ext *ocv1.ClusterExtension) (controllers.RevisionStates, error) {
 	if m.Err != nil {
 		return nil, m.Err
 	}
@@ -94,7 +94,7 @@ func newClientAndReconciler(t *testing.T, opts ...reconcilerOption) (client.Clie
 
 	d := &deps{
 		RevisionStatesGetter: &MockRevisionStatesGetter{
-			RevisionStates: &controllers.RevisionStates{},
+			RevisionStates: controllers.RevisionStates{},
 		},
 		Finalizers: crfinalizer.NewFinalizers(),
 	}
diff --git a/internal/operator-controller/labels/labels.go b/internal/operator-controller/labels/labels.go
index 16f45ecbb..254ab0bd3 100644
--- a/internal/operator-controller/labels/labels.go
+++ b/internal/operator-controller/labels/labels.go
@@ -44,4 +44,10 @@ const (
 	// that were created during migration from Helm releases. This label is used
 	// to distinguish migrated revisions from those created by normal Boxcutter operation.
 	MigratedFromHelmKey = "olm.operatorframework.io/migrated-from-helm"
+
+	// ClusterExtensionGenerationKey is the annotation key used to record the
+	// generation of the ClusterExtension at the time the ClusterExtensionRevision
+	// was created. This tracks which version of the ClusterExtension spec led to
+	// the creation of this revision.
+	ClusterExtensionGenerationKey = "olm.operatorframework.io/cluster-extension-generation"
 )
diff --git a/manifests/experimental-e2e.yaml b/manifests/experimental-e2e.yaml
index 6536baf93..ad9f28812 100644
--- a/manifests/experimental-e2e.yaml
+++ b/manifests/experimental-e2e.yaml
@@ -628,11 +628,11 @@ spec:
   scope: Cluster
   versions:
   - additionalPrinterColumns:
-    - jsonPath: .status.conditions[?(@.type=='Available')].status
-      name: Available
+    - jsonPath: .status.conditions[?(@.type=='Ready')].status
+      name: Ready
       type: string
-    - jsonPath: .status.conditions[?(@.type=='Progressing')].status
-      name: Progressing
+    - jsonPath: .status.conditions[?(@.type=='Ready')].reason
+      name: Reason
       type: string
     - jsonPath: .metadata.creationTimestamp
       name: Age
@@ -778,16 +778,6 @@ spec:
                 x-kubernetes-validations:
                 - message: phases is immutable
                   rule: self == oldSelf || oldSelf.size() == 0
-              progressDeadlineMinutes:
-                description: |-
-                  progressDeadlineMinutes is an optional field that defines the maximum period
-                  of time in minutes after which an installation should be considered failed and
-                  require manual intervention. This functionality is disabled when no value
-                  is provided. The minimum period is 10 minutes, and the maximum is 720 minutes (12 hours).
-                format: int32
-                maximum: 720
-                minimum: 10
-                type: integer
               revision:
                 description: |-
                   revision is a required, immutable sequence number representing a specific revision
@@ -814,22 +804,16 @@ spec:
                   conditions is an optional list of status conditions describing the state of the
                   ClusterExtensionRevision.
 
-                  The Progressing condition represents whether the revision is actively rolling out:
-                    - When status is True and reason is RollingOut, the ClusterExtensionRevision rollout is actively making progress and is in transition.
-                    - When status is True and reason is Retrying, the ClusterExtensionRevision has encountered an error that could be resolved on subsequent reconciliation attempts.
-                    - When status is True and reason is Succeeded, the ClusterExtensionRevision has reached the desired state.
-                    - When status is False and reason is Blocked, the ClusterExtensionRevision has encountered an error that requires manual intervention for recovery.
+                  The Ready condition represents whether the revision has been successfully rolled out and is ready:
+                    - When status is True and reason is Ready, all ClusterExtensionRevision resources have been applied and all progression probes are successful.
+                    - When status is False and reason is RollingOut, the ClusterExtensionRevision rollout is actively making progress and objects are being applied.
+                    - When status is False and reason is Reconciling, the ClusterExtensionRevision is being reconciled or retrying after an error.
+                    - When status is False and reason is ProbeFailure, one or more objects are failing their readiness probes.
+                    - When status is False and reason is ValidationFailed, the revision failed preflight validation checks.
+                    - When status is False and reason is ObjectCollision, the revision encountered object ownership collisions.
+                    - When status is False and reason is ProgressDeadlineExceeded, the revision has not completed within the specified progress deadline.
+                    - When status is False and reason is Transitioning, the revision's objects are being transitioned to a newer revision.
                     - When status is False and reason is Archived, the ClusterExtensionRevision is archived and not being actively reconciled.
-
-                  The Available condition represents whether the revision has been successfully rolled out and is available:
-                    - When status is True and reason is ProbesSucceeded, the ClusterExtensionRevision has been successfully rolled out and all objects pass their readiness probes.
-                    - When status is False and reason is ProbeFailure, one or more objects are failing their readiness probes during rollout.
-                    - When status is Unknown and reason is Reconciling, the ClusterExtensionRevision has encountered an error that prevented it from observing the probes.
-                    - When status is Unknown and reason is Archived, the ClusterExtensionRevision has been archived and its objects have been torn down.
-                    - When status is Unknown and reason is Migrated, the ClusterExtensionRevision was migrated from an existing release and object status probe results have not yet been observed.
-
-                  The Succeeded condition represents whether the revision has successfully completed its rollout:
-                    - When status is True and reason is Succeeded, the ClusterExtensionRevision has successfully completed its rollout. This condition is set once and persists even if the revision later becomes unavailable.
                 items:
                   description: Condition contains details for one aspect of the current
                     state of this API Resource.
@@ -888,6 +872,77 @@ spec:
                 x-kubernetes-list-map-keys:
                 - type
                 x-kubernetes-list-type: map
+              phaseStatuses:
+                description: |-
+                  phaseStatuses provides detailed status information for each phase in the revision.
+                  Each phase status includes the phase name, current state, any error messages,
+                  and details about failing probes if applicable.
+                items:
+                  description: ClusterExtensionRevisionPhaseStatus describes the status
+                    of a single phase.
+                  properties:
+                    failingProbes:
+                      description: |-
+                        failingProbes lists objects in this phase that are failing their readiness probes.
+                        Only populated when state is Progressing and probes are failing.
+                      items:
+                        description: ClusterExtensionRevisionProbeFailure describes
+                          a failing probe for an object in a phase.
+                        properties:
+                          kind:
+                            description: kind is the Kind of the object failing probes.
+                            type: string
+                          message:
+                            description: message contains the joined probe failure
+                              messages.
+                            type: string
+                          name:
+                            description: name is the name of the object failing probes.
+                            type: string
+                          namespace:
+                            description: |-
+                              namespace is the namespace of the object failing probes.
+                              Empty for cluster-scoped objects.
+                            type: string
+                        required:
+                        - kind
+                        - message
+                        - name
+                        type: object
+                      type: array
+                      x-kubernetes-list-type: atomic
+                    lastTransitionTime:
+                      description: |-
+                        lastTransitionTime is the last time the phase state changed.
+                        This only updates when the state, message, or failingProbes change.
+                      format: date-time
+                      type: string
+                    message:
+                      description: |-
+                        message provides additional context about the phase state.
+                        This may include error messages for failed phases.
+                      type: string
+                    name:
+                      description: name is the name of the phase.
+                      type: string
+                    state:
+                      description: state represents the current state of the phase.
+                      enum:
+                      - Applied
+                      - Progressing
+                      - Failed
+                      - Pending
+                      - Transitioning
+                      type: string
+                  required:
+                  - lastTransitionTime
+                  - name
+                  - state
+                  type: object
+                type: array
+                x-kubernetes-list-map-keys:
+                - name
+                x-kubernetes-list-type: map
             type: object
         type: object
     served: true
diff --git a/manifests/experimental.yaml b/manifests/experimental.yaml
index 0b750139d..dcb18419b 100644
--- a/manifests/experimental.yaml
+++ b/manifests/experimental.yaml
@@ -589,11 +589,11 @@ spec:
   scope: Cluster
   versions:
   - additionalPrinterColumns:
-    - jsonPath: .status.conditions[?(@.type=='Available')].status
-      name: Available
+    - jsonPath: .status.conditions[?(@.type=='Ready')].status
+      name: Ready
       type: string
-    - jsonPath: .status.conditions[?(@.type=='Progressing')].status
-      name: Progressing
+    - jsonPath: .status.conditions[?(@.type=='Ready')].reason
+      name: Reason
       type: string
     - jsonPath: .metadata.creationTimestamp
       name: Age
@@ -739,16 +739,6 @@ spec:
                 x-kubernetes-validations:
                 - message: phases is immutable
                   rule: self == oldSelf || oldSelf.size() == 0
-              progressDeadlineMinutes:
-                description: |-
-                  progressDeadlineMinutes is an optional field that defines the maximum period
-                  of time in minutes after which an installation should be considered failed and
-                  require manual intervention. This functionality is disabled when no value
-                  is provided. The minimum period is 10 minutes, and the maximum is 720 minutes (12 hours).
-                format: int32
-                maximum: 720
-                minimum: 10
-                type: integer
               revision:
                 description: |-
                   revision is a required, immutable sequence number representing a specific revision
@@ -775,22 +765,16 @@ spec:
                   conditions is an optional list of status conditions describing the state of the
                   ClusterExtensionRevision.
 
-                  The Progressing condition represents whether the revision is actively rolling out:
-                    - When status is True and reason is RollingOut, the ClusterExtensionRevision rollout is actively making progress and is in transition.
-                    - When status is True and reason is Retrying, the ClusterExtensionRevision has encountered an error that could be resolved on subsequent reconciliation attempts.
-                    - When status is True and reason is Succeeded, the ClusterExtensionRevision has reached the desired state.
-                    - When status is False and reason is Blocked, the ClusterExtensionRevision has encountered an error that requires manual intervention for recovery.
+                  The Ready condition represents whether the revision has been successfully rolled out and is ready:
+                    - When status is True and reason is Ready, all ClusterExtensionRevision resources have been applied and all progression probes are successful.
+                    - When status is False and reason is RollingOut, the ClusterExtensionRevision rollout is actively making progress and objects are being applied.
+                    - When status is False and reason is Reconciling, the ClusterExtensionRevision is being reconciled or retrying after an error.
+                    - When status is False and reason is ProbeFailure, one or more objects are failing their readiness probes.
+                    - When status is False and reason is ValidationFailed, the revision failed preflight validation checks.
+                    - When status is False and reason is ObjectCollision, the revision encountered object ownership collisions.
+                    - When status is False and reason is ProgressDeadlineExceeded, the revision has not completed within the specified progress deadline.
+                    - When status is False and reason is Transitioning, the revision's objects are being transitioned to a newer revision.
                     - When status is False and reason is Archived, the ClusterExtensionRevision is archived and not being actively reconciled.
-
-                  The Available condition represents whether the revision has been successfully rolled out and is available:
-                    - When status is True and reason is ProbesSucceeded, the ClusterExtensionRevision has been successfully rolled out and all objects pass their readiness probes.
-                    - When status is False and reason is ProbeFailure, one or more objects are failing their readiness probes during rollout.
-                    - When status is Unknown and reason is Reconciling, the ClusterExtensionRevision has encountered an error that prevented it from observing the probes.
-                    - When status is Unknown and reason is Archived, the ClusterExtensionRevision has been archived and its objects have been torn down.
-                    - When status is Unknown and reason is Migrated, the ClusterExtensionRevision was migrated from an existing release and object status probe results have not yet been observed.
-
-                  The Succeeded condition represents whether the revision has successfully completed its rollout:
-                    - When status is True and reason is Succeeded, the ClusterExtensionRevision has successfully completed its rollout. This condition is set once and persists even if the revision later becomes unavailable.
                 items:
                   description: Condition contains details for one aspect of the current
                     state of this API Resource.
@@ -849,6 +833,77 @@ spec:
                 x-kubernetes-list-map-keys:
                 - type
                 x-kubernetes-list-type: map
+              phaseStatuses:
+                description: |-
+                  phaseStatuses provides detailed status information for each phase in the revision.
+                  Each phase status includes the phase name, current state, any error messages,
+                  and details about failing probes if applicable.
+                items:
+                  description: ClusterExtensionRevisionPhaseStatus describes the status
+                    of a single phase.
+                  properties:
+                    failingProbes:
+                      description: |-
+                        failingProbes lists objects in this phase that are failing their readiness probes.
+                        Only populated when state is Progressing and probes are failing.
+                      items:
+                        description: ClusterExtensionRevisionProbeFailure describes
+                          a failing probe for an object in a phase.
+                        properties:
+                          kind:
+                            description: kind is the Kind of the object failing probes.
+                            type: string
+                          message:
+                            description: message contains the joined probe failure
+                              messages.
+                            type: string
+                          name:
+                            description: name is the name of the object failing probes.
+                            type: string
+                          namespace:
+                            description: |-
+                              namespace is the namespace of the object failing probes.
+                              Empty for cluster-scoped objects.
+                            type: string
+                        required:
+                        - kind
+                        - message
+                        - name
+                        type: object
+                      type: array
+                      x-kubernetes-list-type: atomic
+                    lastTransitionTime:
+                      description: |-
+                        lastTransitionTime is the last time the phase state changed.
+                        This only updates when the state, message, or failingProbes change.
+                      format: date-time
+                      type: string
+                    message:
+                      description: |-
+                        message provides additional context about the phase state.
+                        This may include error messages for failed phases.
+                      type: string
+                    name:
+                      description: name is the name of the phase.
+                      type: string
+                    state:
+                      description: state represents the current state of the phase.
+                      enum:
+                      - Applied
+                      - Progressing
+                      - Failed
+                      - Pending
+                      - Transitioning
+                      type: string
+                  required:
+                  - lastTransitionTime
+                  - name
+                  - state
+                  type: object
+                type: array
+                x-kubernetes-list-map-keys:
+                - name
+                x-kubernetes-list-type: map
             type: object
         type: object
     served: true
diff --git a/testdata/images/catalogs/test-catalog/v1/configs/catalog.yaml b/testdata/images/catalogs/test-catalog/v1/configs/catalog.yaml
index 012afbe83..82d01105b 100644
--- a/testdata/images/catalogs/test-catalog/v1/configs/catalog.yaml
+++ b/testdata/images/catalogs/test-catalog/v1/configs/catalog.yaml
@@ -17,8 +17,12 @@ entries:
   - name: test-operator.1.0.0
   - name: test-operator.1.0.1
     replaces: test-operator.1.0.0
-  - name: test-operator.1.2.0
+  - name: test-operator.1.0.2
     replaces: test-operator.1.0.1
+  - name: test-operator.1.0.3
+    replaces: test-operator.1.0.2
+  - name: test-operator.1.2.0
+    replaces: test-operator.1.0.3
 ---
 schema: olm.bundle
 name: test-operator.1.0.0