diff --git a/packages/agent/src/adapters/claude/claude-agent.ts b/packages/agent/src/adapters/claude/claude-agent.ts
index dc704c0d2..a715cb510 100644
--- a/packages/agent/src/adapters/claude/claude-agent.ts
+++ b/packages/agent/src/adapters/claude/claude-agent.ts
@@ -1047,6 +1047,9 @@ export class ClaudeAcpAgent extends BaseAcpAgent {
     }
     const previousMode = this.session.permissionMode;
     this.session.permissionMode = modeId as CodeExecutionMode;
+    if (modeId === "plan" && previousMode !== "plan") {
+      this.session.modeBeforePlan = previousMode;
+    }
     try {
       await this.session.query.setPermissionMode(modeId as CodeExecutionMode);
     } catch (error) {
@@ -1343,7 +1346,11 @@ export class ClaudeAcpAgent extends BaseAcpAgent {
   private createOnModeChange() {
     return async (newMode: CodeExecutionMode) => {
       if (this.session) {
+        const previousMode = this.session.permissionMode;
         this.session.permissionMode = newMode;
+        if (newMode === "plan" && previousMode !== "plan") {
+          this.session.modeBeforePlan = previousMode;
+        }
       }
       await this.updateConfigOption("mode", newMode);
     };
diff --git a/packages/agent/src/adapters/claude/permissions/permission-handlers.ts b/packages/agent/src/adapters/claude/permissions/permission-handlers.ts
index 1f515bcf3..f9e6293c7 100644
--- a/packages/agent/src/adapters/claude/permissions/permission-handlers.ts
+++ b/packages/agent/src/adapters/claude/permissions/permission-handlers.ts
@@ -142,7 +142,7 @@ async function requestPlanApproval(
   context: ToolHandlerContext,
   updatedInput: Record<string, unknown>,
 ): Promise<RequestPermissionResponse> {
-  const { client, sessionId, toolUseID } = context;
+  const { client, sessionId, toolUseID, session } = context;
 
   const toolInfo = toolInfoFromToolUse({
     name: context.toolName,
@@ -150,7 +150,7 @@ async function requestPlanApproval(
   });
 
   return await client.requestPermission({
-    options: buildExitPlanModePermissionOptions(),
+    options: buildExitPlanModePermissionOptions(session.modeBeforePlan),
     sessionId,
     toolCall: {
       toolCallId: toolUseID,
diff --git a/packages/agent/src/adapters/claude/permissions/permission-options.test.ts b/packages/agent/src/adapters/claude/permissions/permission-options.test.ts
new file mode 100644
index 000000000..b41c49318
--- /dev/null
+++ b/packages/agent/src/adapters/claude/permissions/permission-options.test.ts
@@ -0,0 +1,51 @@
+import { describe, expect, it } from "vitest";
+import { buildExitPlanModePermissionOptions } from "./permission-options";
+
+describe("buildExitPlanModePermissionOptions", () => {
+  it("does not relabel any option when no previous mode is provided", () => {
+    const options = buildExitPlanModePermissionOptions();
+    for (const opt of options) {
+      expect(opt.name).not.toMatch(/^Yes, continue/);
+    }
+    expect(options[options.length - 1].optionId).toBe("reject_with_feedback");
+  });
+
+  it("promotes the previous mode to the first position with a continue label", () => {
+    const options = buildExitPlanModePermissionOptions("default");
+    expect(options[0]).toMatchObject({
+      optionId: "default",
+      name: "Yes, continue manually approving edits",
+    });
+    expect(options[options.length - 1].optionId).toBe("reject_with_feedback");
+  });
+
+  it("relabels the auto option when it is the previous mode", () => {
+    const options = buildExitPlanModePermissionOptions("auto");
+    expect(options[0]).toMatchObject({
+      optionId: "auto",
+      name: 'Yes, continue in "auto" mode',
+    });
+  });
+
+  it("relabels the acceptEdits option when it is the previous mode", () => {
+    const options = buildExitPlanModePermissionOptions("acceptEdits");
+    expect(options[0]).toMatchObject({
+      optionId: "acceptEdits",
+      name: "Yes, continue auto-accepting edits",
+    });
+  });
+
+  it("ignores an unknown previous mode", () => {
+    const options = buildExitPlanModePermissionOptions("plan");
+    expect(options[0].name).toMatch(/^Yes, /);
+    expect(options[0].name).not.toMatch(/^Yes, continue/);
+    expect(options[options.length - 1].optionId).toBe("reject_with_feedback");
+  });
+
+  it("always keeps the reject option last", () => {
+    for (const previousMode of ["auto", "acceptEdits", "default", undefined]) {
+      const options = buildExitPlanModePermissionOptions(previousMode);
+      expect(options[options.length - 1].optionId).toBe("reject_with_feedback");
+    }
+  });
+});
diff --git a/packages/agent/src/adapters/claude/permissions/permission-options.ts b/packages/agent/src/adapters/claude/permissions/permission-options.ts
index fdaa8b530..ff658b536 100644
--- a/packages/agent/src/adapters/claude/permissions/permission-options.ts
+++ b/packages/agent/src/adapters/claude/permissions/permission-options.ts
@@ -92,7 +92,16 @@ export function buildPermissionOptions(
   return permissionOptions("Yes, always allow");
 }
 
-export function buildExitPlanModePermissionOptions(): PermissionOption[] {
+const CONTINUE_LABELS: Record<string, string> = {
+  auto: 'Yes, continue in "auto" mode',
+  acceptEdits: "Yes, continue auto-accepting edits",
+  default: "Yes, continue manually approving edits",
+  bypassPermissions: "Yes, continue bypassing all permissions",
+};
+
+export function buildExitPlanModePermissionOptions(
+  previousMode?: string,
+): PermissionOption[] {
   const options: PermissionOption[] = [];
 
   if (ALLOW_BYPASS) {
@@ -119,13 +128,30 @@ export function buildExitPlanModePermissionOptions(): PermissionOption[] {
       name: "Yes, and manually approve edits",
       optionId: "default",
     },
-    {
-      kind: "reject_once",
-      name: "No, and tell the agent what to do differently",
-      optionId: "reject_with_feedback",
-      _meta: { customInput: true },
-    },
   );
 
+  const previousIndex = previousMode
+    ? options.findIndex((opt) => opt.optionId === previousMode)
+    : -1;
+  if (previousIndex > 0) {
+    const [previous] = options.splice(previousIndex, 1);
+    const continueLabel = CONTINUE_LABELS[previous.optionId];
+    options.unshift(
+      continueLabel ? { ...previous, name: continueLabel } : previous,
+    );
+  } else if (previousIndex === 0) {
+    const continueLabel = CONTINUE_LABELS[options[0].optionId];
+    if (continueLabel) {
+      options[0] = { ...options[0], name: continueLabel };
+    }
+  }
+
+  options.push({
+    kind: "reject_once",
+    name: "No, and tell the agent what to do differently",
+    optionId: "reject_with_feedback",
+    _meta: { customInput: true },
+  });
+
   return options;
 }
diff --git a/packages/agent/src/adapters/claude/types.ts b/packages/agent/src/adapters/claude/types.ts
index 91c106ff5..1efd77258 100644
--- a/packages/agent/src/adapters/claude/types.ts
+++ b/packages/agent/src/adapters/claude/types.ts
@@ -46,6 +46,7 @@ export type Session = BaseSession & {
   input: Pushable<SDKUserMessage>;
   settingsManager: SettingsManager;
   permissionMode: CodeExecutionMode;
+  modeBeforePlan?: CodeExecutionMode;
   modelId?: string;
   cwd: string;
   taskRunId?: string;