diff --git a/packages/core/src/permissions/permission-manager.test.ts b/packages/core/src/permissions/permission-manager.test.ts
index 5ee73ee0e28..8166529c064 100644
--- a/packages/core/src/permissions/permission-manager.test.ts
+++ b/packages/core/src/permissions/permission-manager.test.ts
@@ -2743,6 +2743,45 @@ describe('PermissionManager', () => {
       expect(await pm.isToolEnabled('structured_output')).toBe(true);
     });
 
+    it('plan-mode lifecycle tools are exempt from the allowlist (#9827)', async () => {
+      // Under the exact reporter configuration the plan-mode system reminder
+      // still instructs the model to call exit_plan_mode, so the sanctioned
+      // plan-flow tools must stay registered. Same synthetic-system-tool
+      // exemption class as structured_output.
+      pm = new PermissionManager(
+        makeConfig({
+          permissionsAllow: [
+            'ReadFile',
+            'WriteFile',
+            'Edit',
+            'Grep',
+            'Glob',
+            'ListFiles',
+            'Shell',
+            'WebFetch',
+          ],
+        }),
+      );
+      pm.initialize();
+      expect(pm.isPermissionsAllowListActive()).toBe(true);
+      expect(await pm.isToolEnabled('exit_plan_mode')).toBe(true);
+      expect(await pm.isToolEnabled('enter_plan_mode')).toBe(true);
+      expect(await pm.isToolEnabled('ask_user_question')).toBe(true);
+      // Unrelated unlisted built-ins stay gated.
+      expect(await pm.isToolEnabled('send_message')).toBe(false);
+    });
+
+    it('a whole-tool deny rule still wins over the plan-mode exemption', async () => {
+      pm = new PermissionManager(
+        makeConfig({
+          permissionsAllow: ['read_file'],
+          permissionsDeny: ['exit_plan_mode'],
+        }),
+      );
+      pm.initialize();
+      expect(await pm.isToolEnabled('exit_plan_mode')).toBe(false);
+    });
+
     it('session-granted allow rules extend membership but never activate the allowlist', async () => {
       // No configured allow rules → allowlist must stay inactive even after
       // a mid-session "Always allow" / skill allowedTools grant, or one
diff --git a/packages/core/src/permissions/permission-manager.ts b/packages/core/src/permissions/permission-manager.ts
index b28fa529c65..36f51b8aed8 100644
--- a/packages/core/src/permissions/permission-manager.ts
+++ b/packages/core/src/permissions/permission-manager.ts
@@ -632,6 +632,22 @@ export class PermissionManager {
     'monitor',
   ]);
 
+  /**
+   * Synthetic plan-mode lifecycle tools that must stay registered even under
+   * an active `permissions.allow` registry allowlist. The plan-mode system
+   * reminder instructs the model to present its plan by calling
+   * `exit_plan_mode`, and `enter_plan_mode` / `ask_user_question` are the
+   * sanctioned plan-flow entry and clarification tools; dropping their
+   * schemas makes the plan flow impossible to complete (#9827). They belong
+   * to the same exemption class as `structured_output` and the "synthetic
+   * system tools" the CORE_TOOLS docstring names — deny rules still apply.
+   */
+  private static readonly PLAN_LIFECYCLE_TOOLS: ReadonlySet<string> = new Set([
+    ToolNames.EXIT_PLAN_MODE,
+    ToolNames.ENTER_PLAN_MODE,
+    ToolNames.ASK_USER_QUESTION,
+  ]);
+
   /**
    * Check if a tool is a core tool subject to the coreTools allowlist check.
    */
@@ -675,9 +691,14 @@ export class PermissionManager {
     // - `structured_output`: the synthetic terminal contract for
     //   `--json-schema` runs; removing it leaves such runs with no way to
     //   finish (deny rules still apply to it).
+    // - Plan-mode lifecycle tools (`exit_plan_mode` / `enter_plan_mode` /
+    //   `ask_user_question`): the plan-mode system reminder tells the model
+    //   to call `exit_plan_mode` to present a plan, so their schemas must
+    //   reach the model for the sanctioned plan flow to complete (#9827).
     if (
       this.permissionsAllowListActive &&
       canonicalName !== ToolNames.STRUCTURED_OUTPUT &&
+      !PermissionManager.PLAN_LIFECYCLE_TOOLS.has(canonicalName) &&
       !canonicalName.startsWith('mcp__') &&
       !this.isCoveredByAllowRule(canonicalName)
     ) {