diff --git a/integration-tests/plan-mode.test.ts b/integration-tests/plan-mode.test.ts
index a4af47252c..8709aac189 100644
--- a/integration-tests/plan-mode.test.ts
+++ b/integration-tests/plan-mode.test.ts
@@ -182,10 +182,7 @@ describe('Plan Mode', () => {
         'I want to perform a complex refactoring. Please enter plan mode so we can design it first.',
     });
 
-    const enterPlanCallFound = await rig.waitForToolCall(
-      'enter_plan_mode',
-      10000,
-    );
+    const enterPlanCallFound = await rig.waitForToolCall('enter_plan_mode');
     expect(enterPlanCallFound, 'Expected enter_plan_mode to be called').toBe(
       true,
     );
diff --git a/packages/core/src/config/config.test.ts b/packages/core/src/config/config.test.ts
index ad8af8656c..83ee54f8e0 100644
--- a/packages/core/src/config/config.test.ts
+++ b/packages/core/src/config/config.test.ts
@@ -223,8 +223,6 @@ import type {
   ModelConfigService,
   ModelConfigServiceConfig,
 } from '../services/modelConfigService.js';
-import { ExitPlanModeTool } from '../tools/exit-plan-mode.js';
-import { EnterPlanModeTool } from '../tools/enter-plan-mode.js';
 import { LocalLiteRtLmClient } from '../core/localLiteRtLmClient.js';
 
 vi.mock('../core/baseLlmClient.js');
@@ -1204,6 +1202,28 @@ describe('Server Config (config.ts)', () => {
       expect(SubAgentToolMock).not.toHaveBeenCalled();
     });
 
+    it('should register EnterPlanModeTool and ExitPlanModeTool when plan is enabled', async () => {
+      const params: ConfigParameters = {
+        ...baseParams,
+        plan: true,
+      };
+      const config = new Config(params);
+
+      await config.initialize();
+
+      const registerToolMock = (
+        (await vi.importMock('../tools/tool-registry')) as {
+          ToolRegistry: { prototype: { registerTool: Mock } };
+        }
+      ).ToolRegistry.prototype.registerTool;
+
+      const registeredTools = registerToolMock.mock.calls.map(
+        (call) => call[0].constructor.name,
+      );
+      expect(registeredTools).toContain('EnterPlanModeTool');
+      expect(registeredTools).toContain('ExitPlanModeTool');
+    });
+
     describe('with minified tool class names', () => {
       beforeEach(() => {
         Object.defineProperty(
@@ -2961,131 +2981,6 @@ describe('Plans Directory Initialization', () => {
     expect(fs.promises.mkdir).not.toHaveBeenCalledWith(plansDir, {
       recursive: true,
     });
-
-    const context = config.getWorkspaceContext();
-    expect(context.getDirectories()).not.toContain(plansDir);
-  });
-});
-
-describe('syncPlanModeTools', () => {
-  const baseParams: ConfigParameters = {
-    sessionId: 'test-session',
-    targetDir: '.',
-    debugMode: false,
-    model: 'test-model',
-    cwd: '.',
-  };
-
-  it('should register ExitPlanModeTool and unregister EnterPlanModeTool when in PLAN mode', async () => {
-    const config = new Config({
-      ...baseParams,
-      approvalMode: ApprovalMode.PLAN,
-    });
-    const registry = new ToolRegistry(config, config.getMessageBus());
-    vi.spyOn(config, 'getToolRegistry').mockReturnValue(registry);
-
-    const registerSpy = vi.spyOn(registry, 'registerTool');
-    const unregisterSpy = vi.spyOn(registry, 'unregisterTool');
-    const getToolSpy = vi.spyOn(registry, 'getTool');
-
-    getToolSpy.mockImplementation((name) => {
-      if (name === 'enter_plan_mode')
-        return new EnterPlanModeTool(config, config.getMessageBus());
-      return undefined;
-    });
-
-    config.syncPlanModeTools();
-
-    expect(unregisterSpy).toHaveBeenCalledWith('enter_plan_mode');
-    expect(registerSpy).toHaveBeenCalledWith(expect.anything());
-    const registeredTool = registerSpy.mock.calls[0][0];
-    const { ExitPlanModeTool } = await import('../tools/exit-plan-mode.js');
-    expect(registeredTool).toBeInstanceOf(ExitPlanModeTool);
-  });
-
-  it('should register EnterPlanModeTool and unregister ExitPlanModeTool when NOT in PLAN mode and experimental.plan is enabled', async () => {
-    const config = new Config({
-      ...baseParams,
-      approvalMode: ApprovalMode.DEFAULT,
-      plan: true,
-    });
-    const registry = new ToolRegistry(config, config.getMessageBus());
-    vi.spyOn(config, 'getToolRegistry').mockReturnValue(registry);
-
-    const registerSpy = vi.spyOn(registry, 'registerTool');
-    const unregisterSpy = vi.spyOn(registry, 'unregisterTool');
-    const getToolSpy = vi.spyOn(registry, 'getTool');
-
-    getToolSpy.mockImplementation((name) => {
-      if (name === 'exit_plan_mode')
-        return new ExitPlanModeTool(config, config.getMessageBus());
-      return undefined;
-    });
-
-    config.syncPlanModeTools();
-
-    expect(unregisterSpy).toHaveBeenCalledWith('exit_plan_mode');
-    expect(registerSpy).toHaveBeenCalledWith(expect.anything());
-    const registeredTool = registerSpy.mock.calls[0][0];
-    const { EnterPlanModeTool } = await import('../tools/enter-plan-mode.js');
-    expect(registeredTool).toBeInstanceOf(EnterPlanModeTool);
-  });
-
-  it('should NOT register EnterPlanModeTool when experimental.plan is disabled', async () => {
-    const config = new Config({
-      ...baseParams,
-      approvalMode: ApprovalMode.DEFAULT,
-      plan: false,
-    });
-    const registry = new ToolRegistry(config, config.getMessageBus());
-    vi.spyOn(config, 'getToolRegistry').mockReturnValue(registry);
-
-    const registerSpy = vi.spyOn(registry, 'registerTool');
-    vi.spyOn(registry, 'getTool').mockReturnValue(undefined);
-
-    config.syncPlanModeTools();
-
-    const { EnterPlanModeTool } = await import('../tools/enter-plan-mode.js');
-    const registeredTool = registerSpy.mock.calls.find(
-      (call) => call[0] instanceof EnterPlanModeTool,
-    );
-    expect(registeredTool).toBeUndefined();
-  });
-
-  it('should NOT register EnterPlanModeTool when in YOLO mode, even if plan is enabled', async () => {
-    const config = new Config({
-      ...baseParams,
-      approvalMode: ApprovalMode.YOLO,
-      plan: true,
-    });
-    const registry = new ToolRegistry(config, config.getMessageBus());
-    vi.spyOn(config, 'getToolRegistry').mockReturnValue(registry);
-
-    const registerSpy = vi.spyOn(registry, 'registerTool');
-    vi.spyOn(registry, 'getTool').mockReturnValue(undefined);
-
-    config.syncPlanModeTools();
-
-    const { EnterPlanModeTool } = await import('../tools/enter-plan-mode.js');
-    const registeredTool = registerSpy.mock.calls.find(
-      (call) => call[0] instanceof EnterPlanModeTool,
-    );
-    expect(registeredTool).toBeUndefined();
-  });
-
-  it('should call geminiClient.setTools if initialized', async () => {
-    const config = new Config(baseParams);
-    const registry = new ToolRegistry(config, config.getMessageBus());
-    vi.spyOn(config, 'getToolRegistry').mockReturnValue(registry);
-    const client = config.getGeminiClient();
-    vi.spyOn(client, 'isInitialized').mockReturnValue(true);
-    const setToolsSpy = vi
-      .spyOn(client, 'setTools')
-      .mockResolvedValue(undefined);
-
-    config.syncPlanModeTools();
-
-    expect(setToolsSpy).toHaveBeenCalled();
   });
 });
 
diff --git a/packages/core/src/config/config.ts b/packages/core/src/config/config.ts
index 87633d35b6..1a5c14b12c 100644
--- a/packages/core/src/config/config.ts
+++ b/packages/core/src/config/config.ts
@@ -370,10 +370,6 @@ import { McpClientManager } from '../tools/mcp-client-manager.js';
 import { type McpContext } from '../tools/mcp-client.js';
 import type { EnvironmentSanitizationConfig } from '../services/environmentSanitization.js';
 import { getErrorMessage } from '../utils/errors.js';
-import {
-  ENTER_PLAN_MODE_TOOL_NAME,
-  EXIT_PLAN_MODE_TOOL_NAME,
-} from '../tools/tool-names.js';
 
 export type { FileFilteringOptions };
 export {
@@ -1172,7 +1168,6 @@ export class Config implements McpContext {
     }
 
     await this.geminiClient.initialize();
-    this.syncPlanModeTools();
     this.initialized = true;
   }
 
@@ -1998,52 +1993,15 @@ export class Config implements McpContext {
       (currentMode === ApprovalMode.YOLO || mode === ApprovalMode.YOLO);
 
     if (isPlanModeTransition || isYoloModeTransition) {
-      this.syncPlanModeTools();
+      if (this.geminiClient?.isInitialized()) {
+        this.geminiClient.setTools().catch((err) => {
+          debugLogger.error('Failed to update tools', err);
+        });
+      }
       this.updateSystemInstructionIfInitialized();
     }
   }
 
-  /**
-   * Synchronizes enter/exit plan mode tools based on current mode.
-   */
-  syncPlanModeTools(): void {
-    const registry = this.getToolRegistry();
-    if (!registry) {
-      return;
-    }
-    const approvalMode = this.getApprovalMode();
-    const isPlanMode = approvalMode === ApprovalMode.PLAN;
-    const isYoloMode = approvalMode === ApprovalMode.YOLO;
-
-    if (isPlanMode) {
-      if (registry.getTool(ENTER_PLAN_MODE_TOOL_NAME)) {
-        registry.unregisterTool(ENTER_PLAN_MODE_TOOL_NAME);
-      }
-      if (!registry.getTool(EXIT_PLAN_MODE_TOOL_NAME)) {
-        registry.registerTool(new ExitPlanModeTool(this, this.messageBus));
-      }
-    } else {
-      if (registry.getTool(EXIT_PLAN_MODE_TOOL_NAME)) {
-        registry.unregisterTool(EXIT_PLAN_MODE_TOOL_NAME);
-      }
-      if (this.planEnabled && !isYoloMode) {
-        if (!registry.getTool(ENTER_PLAN_MODE_TOOL_NAME)) {
-          registry.registerTool(new EnterPlanModeTool(this, this.messageBus));
-        }
-      } else {
-        if (registry.getTool(ENTER_PLAN_MODE_TOOL_NAME)) {
-          registry.unregisterTool(ENTER_PLAN_MODE_TOOL_NAME);
-        }
-      }
-    }
-
-    if (this.geminiClient?.isInitialized()) {
-      this.geminiClient.setTools().catch((err) => {
-        debugLogger.error('Failed to update tools', err);
-      });
-    }
-  }
-
   /**
    * Logs the duration of the current approval mode.
    */
diff --git a/packages/core/src/policy/policies/plan.toml b/packages/core/src/policy/policies/plan.toml
index a490e589b0..1af21ba9b6 100644
--- a/packages/core/src/policy/policies/plan.toml
+++ b/packages/core/src/policy/policies/plan.toml
@@ -5,20 +5,21 @@
 #
 # Priority bands (tiers):
 # - Default policies (TOML): 1 + priority/1000 (e.g., priority 100 → 1.100)
-# - Workspace policies (TOML): 2 + priority/1000 (e.g., priority 100 → 2.100)
-# - User policies (TOML): 3 + priority/1000 (e.g., priority 100 → 3.100)
-# - Admin policies (TOML): 4 + priority/1000 (e.g., priority 100 → 4.100)
+# - Extension policies (TOML): 2 + priority/1000 (e.g., priority 100 → 2.100)
+# - Workspace policies (TOML): 3 + priority/1000 (e.g., priority 100 → 3.100)
+# - User policies (TOML): 4 + priority/1000 (e.g., priority 100 → 4.100)
+# - Admin policies (TOML): 5 + priority/1000 (e.g., priority 100 → 5.100)
 #
-# This ensures Admin > User > Workspace > Default hierarchy is always preserved,
+# This ensures Admin > User > Workspace > Extension > Default hierarchy is always preserved,
 # while allowing user-specified priorities to work within each tier.
 #
-# Settings-based and dynamic rules (all in user tier 3.x):
-#   3.95: Tools that the user has selected as "Always Allow" in the interactive UI
-#   3.9:  MCP servers excluded list (security: persistent server blocks)
-#   3.4:  Command line flag --exclude-tools (explicit temporary blocks)
-#   3.3:  Command line flag --allowed-tools (explicit temporary allows)
-#   3.2:  MCP servers with trust=true (persistent trusted servers)
-#   3.1:  MCP servers allowed list (persistent general server allows)
+# Settings-based and dynamic rules (all in user tier 4.x):
+#   4.95: Tools that the user has selected as "Always Allow" in the interactive UI
+#   4.9:  MCP servers excluded list (security: persistent server blocks)
+#   4.4:  Command line flag --exclude-tools (explicit temporary blocks)
+#   4.3:  Command line flag --allowed-tools (explicit temporary allows)
+#   4.2:  MCP servers with trust=true (persistent trusted servers)
+#   4.1:  MCP servers allowed list (persistent general server allows)
 #
 # TOML policy priorities (before transformation):
 #   10: Write tools default to ASK_USER (becomes 1.010 in default tier)
@@ -26,6 +27,33 @@
 #   70: Plan mode explicit ALLOW override (becomes 1.070 in default tier)
 #   999: YOLO mode allow-all (becomes 1.999 in default tier)
 
+# Mode Transitions (into/out of Plan Mode)
+
+[[rule]]
+toolName = "enter_plan_mode"
+decision = "ask_user"
+priority = 50
+
+[[rule]]
+toolName = "enter_plan_mode"
+decision = "deny"
+priority = 70
+modes = ["plan"]
+deny_message = "You are already in Plan Mode."
+
+[[rule]]
+toolName = "exit_plan_mode"
+decision = "ask_user"
+priority = 70
+modes = ["plan"]
+
+[[rule]]
+toolName = "exit_plan_mode"
+decision = "deny"
+priority = 50
+deny_message = "You are not currently in Plan Mode. Use enter_plan_mode first to design a plan."
+
+
 # Catch-All: Deny everything by default in Plan mode.
 
 [[rule]]
@@ -50,7 +78,7 @@ priority = 70
 modes = ["plan"]
 
 [[rule]]
-toolName = ["ask_user", "exit_plan_mode", "save_memory"]
+toolName = ["ask_user", "save_memory"]
 decision = "ask_user"
 priority = 70
 modes = ["plan"]
diff --git a/packages/core/src/policy/policies/read-only.toml b/packages/core/src/policy/policies/read-only.toml
index 1688d5108c..c9c96923e7 100644
--- a/packages/core/src/policy/policies/read-only.toml
+++ b/packages/core/src/policy/policies/read-only.toml
@@ -5,20 +5,21 @@
 #
 # Priority bands (tiers):
 # - Default policies (TOML): 1 + priority/1000 (e.g., priority 100 → 1.100)
-# - Workspace policies (TOML): 2 + priority/1000 (e.g., priority 100 → 2.100)
-# - User policies (TOML): 3 + priority/1000 (e.g., priority 100 → 3.100)
-# - Admin policies (TOML): 4 + priority/1000 (e.g., priority 100 → 4.100)
+# - Extension policies (TOML): 2 + priority/1000 (e.g., priority 100 → 2.100)
+# - Workspace policies (TOML): 3 + priority/1000 (e.g., priority 100 → 3.100)
+# - User policies (TOML): 4 + priority/1000 (e.g., priority 100 → 4.100)
+# - Admin policies (TOML): 5 + priority/1000 (e.g., priority 100 → 5.100)
 #
-# This ensures Admin > User > Workspace > Default hierarchy is always preserved,
+# This ensures Admin > User > Workspace > Extension > Default hierarchy is always preserved,
 # while allowing user-specified priorities to work within each tier.
 #
-# Settings-based and dynamic rules (all in user tier 3.x):
-#   3.95: Tools that the user has selected as "Always Allow" in the interactive UI
-#   3.9:  MCP servers excluded list (security: persistent server blocks)
-#   3.4:  Command line flag --exclude-tools (explicit temporary blocks)
-#   3.3:  Command line flag --allowed-tools (explicit temporary allows)
-#   3.2:  MCP servers with trust=true (persistent trusted servers)
-#   3.1:  MCP servers allowed list (persistent general server allows)
+# Settings-based and dynamic rules (all in user tier 4.x):
+#   4.95: Tools that the user has selected as "Always Allow" in the interactive UI
+#   4.9:  MCP servers excluded list (security: persistent server blocks)
+#   4.4:  Command line flag --exclude-tools (explicit temporary blocks)
+#   4.3:  Command line flag --allowed-tools (explicit temporary allows)
+#   4.2:  MCP servers with trust=true (persistent trusted servers)
+#   4.1:  MCP servers allowed list (persistent general server allows)
 #
 # TOML policy priorities (before transformation):
 #   10: Write tools default to ASK_USER (becomes 1.010 in default tier)
diff --git a/packages/core/src/policy/policies/write.toml b/packages/core/src/policy/policies/write.toml
index 47cd9c98ae..c24f6dfee3 100644
--- a/packages/core/src/policy/policies/write.toml
+++ b/packages/core/src/policy/policies/write.toml
@@ -5,20 +5,21 @@
 #
 # Priority bands (tiers):
 # - Default policies (TOML): 1 + priority/1000 (e.g., priority 100 → 1.100)
-# - Workspace policies (TOML): 2 + priority/1000 (e.g., priority 100 → 2.100)
-# - User policies (TOML): 3 + priority/1000 (e.g., priority 100 → 3.100)
-# - Admin policies (TOML): 4 + priority/1000 (e.g., priority 100 → 4.100)
+# - Extension policies (TOML): 2 + priority/1000 (e.g., priority 100 → 2.100)
+# - Workspace policies (TOML): 3 + priority/1000 (e.g., priority 100 → 3.100)
+# - User policies (TOML): 4 + priority/1000 (e.g., priority 100 → 4.100)
+# - Admin policies (TOML): 5 + priority/1000 (e.g., priority 100 → 5.100)
 #
-# This ensures Admin > User > Workspace > Default hierarchy is always preserved,
+# This ensures Admin > User > Workspace > Extension > Default hierarchy is always preserved,
 # while allowing user-specified priorities to work within each tier.
 #
-# Settings-based and dynamic rules (all in user tier 3.x):
-#   3.95: Tools that the user has selected as "Always Allow" in the interactive UI
-#   3.9:  MCP servers excluded list (security: persistent server blocks)
-#   3.4:  Command line flag --exclude-tools (explicit temporary blocks)
-#   3.3:  Command line flag --allowed-tools (explicit temporary allows)
-#   3.2:  MCP servers with trust=true (persistent trusted servers)
-#   3.1:  MCP servers allowed list (persistent general server allows)
+# Settings-based and dynamic rules (all in user tier 4.x):
+#   4.95: Tools that the user has selected as "Always Allow" in the interactive UI
+#   4.9:  MCP servers excluded list (security: persistent server blocks)
+#   4.4:  Command line flag --exclude-tools (explicit temporary blocks)
+#   4.3:  Command line flag --allowed-tools (explicit temporary allows)
+#   4.2:  MCP servers with trust=true (persistent trusted servers)
+#   4.1:  MCP servers allowed list (persistent general server allows)
 #
 # TOML policy priorities (before transformation):
 #   10: Write tools default to ASK_USER (becomes 1.010 in default tier)
diff --git a/packages/core/src/policy/policies/yolo.toml b/packages/core/src/policy/policies/yolo.toml
index 332334db7c..d326e163f5 100644
--- a/packages/core/src/policy/policies/yolo.toml
+++ b/packages/core/src/policy/policies/yolo.toml
@@ -5,20 +5,21 @@
 #
 # Priority bands (tiers):
 # - Default policies (TOML): 1 + priority/1000 (e.g., priority 100 → 1.100)
-# - Workspace policies (TOML): 2 + priority/1000 (e.g., priority 100 → 2.100)
-# - User policies (TOML): 3 + priority/1000 (e.g., priority 100 → 3.100)
-# - Admin policies (TOML): 4 + priority/1000 (e.g., priority 100 → 4.100)
+# - Extension policies (TOML): 2 + priority/1000 (e.g., priority 100 → 2.100)
+# - Workspace policies (TOML): 3 + priority/1000 (e.g., priority 100 → 3.100)
+# - User policies (TOML): 4 + priority/1000 (e.g., priority 100 → 4.100)
+# - Admin policies (TOML): 5 + priority/1000 (e.g., priority 100 → 5.100)
 #
-# This ensures Admin > User > Workspace > Default hierarchy is always preserved,
+# This ensures Admin > User > Workspace > Extension > Default hierarchy is always preserved,
 # while allowing user-specified priorities to work within each tier.
 #
-# Settings-based and dynamic rules (all in user tier 3.x):
-#   3.95: Tools that the user has selected as "Always Allow" in the interactive UI
-#   3.9:  MCP servers excluded list (security: persistent server blocks)
-#   3.4:  Command line flag --exclude-tools (explicit temporary blocks)
-#   3.3:  Command line flag --allowed-tools (explicit temporary allows)
-#   3.2:  MCP servers with trust=true (persistent trusted servers)
-#   3.1:  MCP servers allowed list (persistent general server allows)
+# Settings-based and dynamic rules (all in user tier 4.x):
+#   4.95: Tools that the user has selected as "Always Allow" in the interactive UI
+#   4.9:  MCP servers excluded list (security: persistent server blocks)
+#   4.4:  Command line flag --exclude-tools (explicit temporary blocks)
+#   4.3:  Command line flag --allowed-tools (explicit temporary allows)
+#   4.2:  MCP servers with trust=true (persistent trusted servers)
+#   4.1:  MCP servers allowed list (persistent general server allows)
 #
 # TOML policy priorities (before transformation):
 #   10: Write tools default to ASK_USER (becomes 1.010 in default tier)
@@ -36,6 +37,15 @@ decision = "ask_user"
 priority = 999
 modes = ["yolo"]
 
+# Plan mode transitions are blocked in YOLO mode to maintain state consistency
+# and because planning currently requires human interaction (plan approval),
+# which conflicts with YOLO's autonomous nature.
+[[rule]]
+toolName = ["enter_plan_mode", "exit_plan_mode"]
+decision = "deny"
+priority = 999
+modes = ["yolo"]
+
 # Allow everything else in YOLO mode
 [[rule]]
 decision = "allow"
diff --git a/packages/core/src/policy/policy-engine.test.ts b/packages/core/src/policy/policy-engine.test.ts
index f93c9ad3b8..4c9b9cbfcd 100644
--- a/packages/core/src/policy/policy-engine.test.ts
+++ b/packages/core/src/policy/policy-engine.test.ts
@@ -2808,6 +2808,82 @@ describe('PolicyEngine', () => {
         'Execution of scripts (including those from skills) is blocked',
       );
     });
+
+    it('should deny enter_plan_mode when already in PLAN mode', async () => {
+      const rules: PolicyRule[] = [
+        {
+          toolName: 'enter_plan_mode',
+          decision: PolicyDecision.DENY,
+          priority: 70,
+          modes: [ApprovalMode.PLAN],
+          denyMessage: 'You are already in Plan Mode.',
+        },
+      ];
+
+      engine = new PolicyEngine({
+        rules,
+        approvalMode: ApprovalMode.PLAN,
+      });
+
+      const result = await engine.check({ name: 'enter_plan_mode' }, undefined);
+      expect(result.decision).toBe(PolicyDecision.DENY);
+      expect(result.rule?.denyMessage).toBe('You are already in Plan Mode.');
+    });
+
+    it('should deny exit_plan_mode when in DEFAULT mode', async () => {
+      const rules: PolicyRule[] = [
+        {
+          toolName: 'exit_plan_mode',
+          decision: PolicyDecision.DENY,
+          priority: 10,
+          modes: [ApprovalMode.DEFAULT],
+          denyMessage: 'You are not in Plan Mode.',
+        },
+      ];
+
+      engine = new PolicyEngine({
+        rules,
+        approvalMode: ApprovalMode.DEFAULT,
+      });
+
+      const result = await engine.check({ name: 'exit_plan_mode' }, undefined);
+      expect(result.decision).toBe(PolicyDecision.DENY);
+      expect(result.rule?.denyMessage).toBe('You are not in Plan Mode.');
+    });
+
+    it('should deny both plan tools in YOLO mode', async () => {
+      const rules: PolicyRule[] = [
+        {
+          toolName: 'enter_plan_mode',
+          decision: PolicyDecision.DENY,
+          priority: 999,
+          modes: [ApprovalMode.YOLO],
+        },
+        {
+          toolName: 'exit_plan_mode',
+          decision: PolicyDecision.DENY,
+          priority: 999,
+          modes: [ApprovalMode.YOLO],
+        },
+      ];
+
+      engine = new PolicyEngine({
+        rules,
+        approvalMode: ApprovalMode.YOLO,
+      });
+
+      const resultEnter = await engine.check(
+        { name: 'enter_plan_mode' },
+        undefined,
+      );
+      expect(resultEnter.decision).toBe(PolicyDecision.DENY);
+
+      const resultExit = await engine.check(
+        { name: 'exit_plan_mode' },
+        undefined,
+      );
+      expect(resultExit.decision).toBe(PolicyDecision.DENY);
+    });
   });
 
   describe('removeRulesByTier', () => {
diff --git a/packages/core/src/tools/ask-user.ts b/packages/core/src/tools/ask-user.ts
index 6dbec43dda..621d4c10d1 100644
--- a/packages/core/src/tools/ask-user.ts
+++ b/packages/core/src/tools/ask-user.ts
@@ -28,9 +28,11 @@ export class AskUserTool extends BaseDeclarativeTool<
   AskUserParams,
   ToolResult
 > {
+  static readonly Name = ASK_USER_TOOL_NAME;
+
   constructor(messageBus: MessageBus) {
     super(
-      ASK_USER_TOOL_NAME,
+      AskUserTool.Name,
       ASK_USER_DISPLAY_NAME,
       ASK_USER_DEFINITION.base.description!,
       Kind.Communicate,
diff --git a/packages/core/src/tools/enter-plan-mode.ts b/packages/core/src/tools/enter-plan-mode.ts
index 9e1bed23a6..d52c721aae 100644
--- a/packages/core/src/tools/enter-plan-mode.ts
+++ b/packages/core/src/tools/enter-plan-mode.ts
@@ -27,12 +27,14 @@ export class EnterPlanModeTool extends BaseDeclarativeTool<
   EnterPlanModeParams,
   ToolResult
 > {
+  static readonly Name = ENTER_PLAN_MODE_TOOL_NAME;
+
   constructor(
     private config: Config,
     messageBus: MessageBus,
   ) {
     super(
-      ENTER_PLAN_MODE_TOOL_NAME,
+      EnterPlanModeTool.Name,
       'Enter Plan Mode',
       ENTER_PLAN_MODE_DEFINITION.base.description!,
       Kind.Plan,
diff --git a/packages/core/src/tools/exit-plan-mode.ts b/packages/core/src/tools/exit-plan-mode.ts
index 1facdcbf7c..442b00e5cb 100644
--- a/packages/core/src/tools/exit-plan-mode.ts
+++ b/packages/core/src/tools/exit-plan-mode.ts
@@ -35,6 +35,8 @@ export class ExitPlanModeTool extends BaseDeclarativeTool<
   ExitPlanModeParams,
   ToolResult
 > {
+  static readonly Name = EXIT_PLAN_MODE_TOOL_NAME;
+
   constructor(
     private config: Config,
     messageBus: MessageBus,
@@ -42,7 +44,7 @@ export class ExitPlanModeTool extends BaseDeclarativeTool<
     const plansDir = config.storage.getPlansDir();
     const definition = getExitPlanModeDefinition(plansDir);
     super(
-      EXIT_PLAN_MODE_TOOL_NAME,
+      ExitPlanModeTool.Name,
       'Exit Plan Mode',
       definition.base.description!,
       Kind.Plan,