diff --git a/acceptance/bundle/resources/alerts/with_file/alert.dbalert.json b/acceptance/bundle/resources/alerts/with_file/alert.dbalert.json
index d9690fc3c63..e24850a7668 100644
--- a/acceptance/bundle/resources/alerts/with_file/alert.dbalert.json
+++ b/acceptance/bundle/resources/alerts/with_file/alert.dbalert.json
@@ -1,20 +1,20 @@
 {
   "custom_summary": "My alert from file",
   "evaluation": {
+    "comparison_operator": "EQUAL",
+    "notification": {
+      "notify_on_ok": false,
+      "retrigger_seconds": 1
+    },
     "source": {
-      "name": "1",
+      "aggregation": "MAX",
       "display": "1",
-      "aggregation": "MAX"
+      "name": "1"
     },
-    "comparison_operator": "EQUAL",
     "threshold": {
       "value": {
-        "double_value": 2.0
+        "double_value": 2
       }
-    },
-    "notification": {
-      "retrigger_seconds": 1,
-      "notify_on_ok": false
     }
   },
   "schedule": {
diff --git a/acceptance/bundle/resources/alerts/with_file/out.test.toml b/acceptance/bundle/resources/alerts/with_file/out.test.toml
index 650836edeb3..bbc7fcfd1bd 100644
--- a/acceptance/bundle/resources/alerts/with_file/out.test.toml
+++ b/acceptance/bundle/resources/alerts/with_file/out.test.toml
@@ -1,3 +1,3 @@
-Local = false
+Local = true
 Cloud = true
 EnvMatrix.DATABRICKS_BUNDLE_ENGINE = ["terraform", "direct"]
diff --git a/acceptance/bundle/resources/alerts/with_file/test.toml b/acceptance/bundle/resources/alerts/with_file/test.toml
index efeaad4b922..fb1dfd4006a 100644
--- a/acceptance/bundle/resources/alerts/with_file/test.toml
+++ b/acceptance/bundle/resources/alerts/with_file/test.toml
@@ -1,4 +1,4 @@
-Local = false
+Local = true
 Cloud = true
 RecordRequests = false
 Ignore = [".databricks"]
diff --git a/libs/testserver/alerts.go b/libs/testserver/alerts.go
index c5163a056a4..71c751749f9 100644
--- a/libs/testserver/alerts.go
+++ b/libs/testserver/alerts.go
@@ -4,10 +4,83 @@ import (
 	"encoding/json"
 	"fmt"
 	"net/http"
+	"path"
+	"strings"
 
 	"github.com/databricks/databricks-sdk-go/service/sql"
+	"github.com/databricks/databricks-sdk-go/service/workspace"
 )
 
+// alertFile mirrors the schema of a .dbalert.json file. It is the inverse of
+// bundle/config/mutator/load_dbalert_files.go: API-only fields (display_name,
+// warehouse_id) are dropped and the joined query_text/custom_description are
+// split back into lines. The field order matches what the backend materializes.
+type alertFile struct {
+	CustomSummary          string                 `json:"custom_summary,omitempty"`
+	Evaluation             *sql.AlertV2Evaluation `json:"evaluation,omitempty"`
+	Schedule               *sql.CronSchedule      `json:"schedule,omitempty"`
+	QueryLines             []string               `json:"query_lines,omitempty"`
+	CustomDescriptionLines []string               `json:"custom_description_lines,omitempty"`
+}
+
+// alertFilePath returns the workspace path of the .dbalert.json file the backend
+// materializes for an alert: <parent_path>/<display_name>.dbalert.json.
+func alertFilePath(alert sql.AlertV2) string {
+	return path.Join(alert.ParentPath, alert.DisplayName+".dbalert.json")
+}
+
+// splitLines reverses the line-joining done in load_dbalert_files.go: each line
+// is terminated by "\n", so splitting drops the trailing empty element.
+func splitLines(s string) []string {
+	if s == "" {
+		return nil
+	}
+	return strings.Split(strings.TrimSuffix(s, "\n"), "\n")
+}
+
+// writeAlertFile materializes the .dbalert.json file for an alert. On real cloud
+// the backend writes this file as a side effect of alert creation/update, which
+// the `workspace export` round-trip and `bundle generate alert` rely on.
+func (s *FakeWorkspace) writeAlertFile(alert sql.AlertV2) error {
+	if alert.ParentPath == "" || alert.DisplayName == "" {
+		return nil
+	}
+
+	evaluation := alert.Evaluation
+	if evaluation.Notification != nil {
+		// The backend always serializes notify_on_ok in the file, even when
+		// false; the SDK marshaler would otherwise drop the zero value.
+		notification := *evaluation.Notification
+		notification.ForceSendFields = append(notification.ForceSendFields, "NotifyOnOk")
+		evaluation.Notification = &notification
+	}
+
+	af := alertFile{
+		CustomSummary:          alert.CustomSummary,
+		Evaluation:             &evaluation,
+		Schedule:               &alert.Schedule,
+		QueryLines:             splitLines(alert.QueryText),
+		CustomDescriptionLines: splitLines(alert.CustomDescription),
+	}
+
+	data, err := json.MarshalIndent(af, "", "  ")
+	if err != nil {
+		return err
+	}
+	data = append(data, '\n')
+
+	filePath := alertFilePath(alert)
+	s.files[filePath] = FileEntry{
+		Info: workspace.ObjectInfo{
+			ObjectType: "FILE",
+			Path:       filePath,
+			ObjectId:   nextID(),
+		},
+		Data: data,
+	}
+	return nil
+}
+
 func (s *FakeWorkspace) AlertsUpsert(req Request, alertId string) Response {
 	var alert sql.AlertV2
 
@@ -35,6 +108,13 @@ func (s *FakeWorkspace) AlertsUpsert(req Request, alertId string) Response {
 	alert.LifecycleState = sql.AlertLifecycleStateActive
 	s.Alerts[alertId] = alert
 
+	if err := s.writeAlertFile(alert); err != nil {
+		return Response{
+			Body:       fmt.Sprintf("internal error: %s", err),
+			StatusCode: http.StatusInternalServerError,
+		}
+	}
+
 	return Response{
 		StatusCode: 200,
 		Body:       alert,
@@ -51,6 +131,8 @@ func (s *FakeWorkspace) AlertsDelete(alertId string, purge bool) Response {
 		}
 	}
 
+	delete(s.files, alertFilePath(alert))
+
 	if purge {
 		delete(s.Alerts, alertId)
 	} else {
diff --git a/libs/testserver/handlers.go b/libs/testserver/handlers.go
index 8f611a7c7c9..ee56cefe3e6 100644
--- a/libs/testserver/handlers.go
+++ b/libs/testserver/handlers.go
@@ -94,7 +94,20 @@ func AddDefaultHandlers(server *Server) {
 
 	server.Handle("GET", "/api/2.0/workspace/export", func(req Request) any {
 		path := req.URL.Query().Get("path")
-		return req.Workspace.WorkspaceExport(path)
+		data := req.Workspace.WorkspaceExport(path)
+
+		// The filer reads the raw object body via ?direct_download=true, while
+		// the SDK's Workspace.Export (used by `databricks workspace export`)
+		// requests JSON and expects the base64-encoded content field.
+		if req.URL.Query().Get("direct_download") == "true" {
+			return data
+		}
+
+		return Response{
+			Body: workspace.ExportResponse{
+				Content: base64.StdEncoding.EncodeToString(data),
+			},
+		}
 	})
 
 	server.Handle("POST", "/api/2.0/workspace/delete", func(req Request) any {