diff --git a/packages/core/src/core/prompts.test.ts b/packages/core/src/core/prompts.test.ts
index e7fa4901bde..180a7c44a87 100644
--- a/packages/core/src/core/prompts.test.ts
+++ b/packages/core/src/core/prompts.test.ts
@@ -483,6 +483,29 @@ describe('Core System Prompt (prompts.ts)', () => {
         expect(prompt).toMatchSnapshot();
       });
     });
+
+    it('should include YOLO mode instructions in interactive mode', () => {
+      vi.mocked(mockConfig.getApprovalMode).mockReturnValue(ApprovalMode.YOLO);
+      vi.mocked(mockConfig.isInteractive).mockReturnValue(true);
+      const prompt = getCoreSystemPrompt(mockConfig);
+      expect(prompt).toContain('# Autonomous Mode (YOLO)');
+      expect(prompt).toContain('Only use the `ask_user` tool if');
+    });
+
+    it('should NOT include YOLO mode instructions in non-interactive mode', () => {
+      vi.mocked(mockConfig.getApprovalMode).mockReturnValue(ApprovalMode.YOLO);
+      vi.mocked(mockConfig.isInteractive).mockReturnValue(false);
+      const prompt = getCoreSystemPrompt(mockConfig);
+      expect(prompt).not.toContain('# Autonomous Mode (YOLO)');
+    });
+
+    it('should NOT include YOLO mode instructions for DEFAULT mode', () => {
+      vi.mocked(mockConfig.getApprovalMode).mockReturnValue(
+        ApprovalMode.DEFAULT,
+      );
+      const prompt = getCoreSystemPrompt(mockConfig);
+      expect(prompt).not.toContain('# Autonomous Mode (YOLO)');
+    });
   });
 
   describe('Platform-specific and Background Process instructions', () => {
diff --git a/packages/core/src/policy/config.test.ts b/packages/core/src/policy/config.test.ts
index 774214d1011..25f7e4a1500 100644
--- a/packages/core/src/policy/config.test.ts
+++ b/packages/core/src/policy/config.test.ts
@@ -317,8 +317,8 @@ describe('createPolicyEngineConfig', () => {
       (r) => r.decision === PolicyDecision.ALLOW && !r.toolName,
     );
     expect(rule).toBeDefined();
-    // Priority 999 in default tier → 1.999
-    expect(rule?.priority).toBeCloseTo(1.999, 5);
+    // Priority 998 in default tier → 1.998 (999 reserved for ask_user exception)
+    expect(rule?.priority).toBeCloseTo(1.998, 5);
   });
 
   it('should allow edit tool in AUTO_EDIT mode', async () => {
@@ -582,8 +582,8 @@ describe('createPolicyEngineConfig', () => {
       (r) => !r.toolName && r.decision === PolicyDecision.ALLOW,
     );
     expect(wildcardRule).toBeDefined();
-    // Priority 999 in default tier → 1.999
-    expect(wildcardRule?.priority).toBeCloseTo(1.999, 5);
+    // Priority 998 in default tier → 1.998 (999 reserved for ask_user exception)
+    expect(wildcardRule?.priority).toBeCloseTo(1.998, 5);
 
     // Write tool ASK_USER rules are present (from write.toml)
     const writeToolRules = config.rules?.filter(
diff --git a/packages/core/src/policy/policies/yolo.toml b/packages/core/src/policy/policies/yolo.toml
index 052ca6c4d37..95c3b411f1d 100644
--- a/packages/core/src/policy/policies/yolo.toml
+++ b/packages/core/src/policy/policies/yolo.toml
@@ -23,10 +23,21 @@
 #   10: Write tools default to ASK_USER (becomes 1.010 in default tier)
 #   15: Auto-edit tool override (becomes 1.015 in default tier)
 #   50: Read-only tools (becomes 1.050 in default tier)
-#   999: YOLO mode allow-all (becomes 1.999 in default tier)
+#   998: YOLO mode allow-all (becomes 1.998 in default tier)
+#   999: Ask-user tool (becomes 1.999 in default tier)
 
+# Ask-user tool always requires user interaction, even in YOLO mode.
+# This ensures the model can gather user preferences/decisions when needed.
+# Note: In non-interactive mode, this decision is converted to DENY by the policy engine.
 [[rule]]
-decision = "allow"
+toolName = "ask_user"
+decision = "ask_user"
 priority = 999
 modes = ["yolo"]
+
+# Allow everything else in YOLO mode
+[[rule]]
+decision = "allow"
+priority = 998
+modes = ["yolo"]
 allow_redirection = true
diff --git a/packages/core/src/policy/policy-engine.test.ts b/packages/core/src/policy/policy-engine.test.ts
index 93cf89536f4..6c59161af49 100644
--- a/packages/core/src/policy/policy-engine.test.ts
+++ b/packages/core/src/policy/policy-engine.test.ts
@@ -2030,4 +2030,60 @@ describe('PolicyEngine', () => {
       expect(result.decision).toBe(PolicyDecision.DENY);
     });
   });
+
+  describe('YOLO mode with ask_user tool', () => {
+    it('should return ASK_USER for ask_user tool even in YOLO mode', async () => {
+      const rules: PolicyRule[] = [
+        {
+          toolName: 'ask_user',
+          decision: PolicyDecision.ASK_USER,
+          priority: 999,
+          modes: [ApprovalMode.YOLO],
+        },
+        {
+          decision: PolicyDecision.ALLOW,
+          priority: 998,
+          modes: [ApprovalMode.YOLO],
+        },
+      ];
+
+      engine = new PolicyEngine({
+        rules,
+        approvalMode: ApprovalMode.YOLO,
+      });
+
+      const result = await engine.check(
+        { name: 'ask_user', args: {} },
+        undefined,
+      );
+      expect(result.decision).toBe(PolicyDecision.ASK_USER);
+    });
+
+    it('should return ALLOW for other tools in YOLO mode', async () => {
+      const rules: PolicyRule[] = [
+        {
+          toolName: 'ask_user',
+          decision: PolicyDecision.ASK_USER,
+          priority: 999,
+          modes: [ApprovalMode.YOLO],
+        },
+        {
+          decision: PolicyDecision.ALLOW,
+          priority: 998,
+          modes: [ApprovalMode.YOLO],
+        },
+      ];
+
+      engine = new PolicyEngine({
+        rules,
+        approvalMode: ApprovalMode.YOLO,
+      });
+
+      const result = await engine.check(
+        { name: 'run_shell_command', args: { command: 'ls' } },
+        undefined,
+      );
+      expect(result.decision).toBe(PolicyDecision.ALLOW);
+    });
+  });
 });
diff --git a/packages/core/src/prompts/promptProvider.ts b/packages/core/src/prompts/promptProvider.ts
index 8da1a7ed7d2..13c4f0374d1 100644
--- a/packages/core/src/prompts/promptProvider.ts
+++ b/packages/core/src/prompts/promptProvider.ts
@@ -50,6 +50,7 @@ export class PromptProvider {
     const interactiveMode = interactiveOverride ?? config.isInteractive();
     const approvalMode = config.getApprovalMode?.() ?? ApprovalMode.DEFAULT;
     const isPlanMode = approvalMode === ApprovalMode.PLAN;
+    const isYoloMode = approvalMode === ApprovalMode.YOLO;
     const skills = config.getSkillManager().getSkills();
     const toolNames = config.getToolRegistry().getAllToolNames();
     const enabledToolNames = new Set(toolNames);
@@ -183,6 +184,11 @@ export class PromptProvider {
           }),
         ),
         sandbox: this.withSection('sandbox', () => getSandboxMode()),
+        interactiveYoloMode: this.withSection(
+          'interactiveYoloMode',
+          () => true,
+          isYoloMode && interactiveMode,
+        ),
         gitRepo: this.withSection(
           'git',
           () => ({ interactive: interactiveMode }),
diff --git a/packages/core/src/prompts/snippets.legacy.ts b/packages/core/src/prompts/snippets.legacy.ts
index 0d6f429a6a9..8d46fd6a1a4 100644
--- a/packages/core/src/prompts/snippets.legacy.ts
+++ b/packages/core/src/prompts/snippets.legacy.ts
@@ -32,6 +32,7 @@ export interface SystemPromptOptions {
   planningWorkflow?: PlanningWorkflowOptions;
   operationalGuidelines?: OperationalGuidelinesOptions;
   sandbox?: SandboxMode;
+  interactiveYoloMode?: boolean;
   gitRepo?: GitRepoOptions;
   finalReminder?: FinalReminderOptions;
 }
@@ -114,6 +115,8 @@ ${
 
 ${renderOperationalGuidelines(options.operationalGuidelines)}
 
+${renderInteractiveYoloMode(options.interactiveYoloMode)}
+
 ${renderSandbox(options.sandbox)}
 
 ${renderGitRepo(options.gitRepo)}
@@ -293,6 +296,25 @@ You are running outside of a sandbox container, directly on the user's system. F
   }
 }
 
+export function renderInteractiveYoloMode(enabled?: boolean): string {
+  if (!enabled) return '';
+  return `
+# Autonomous Mode (YOLO)
+
+You are operating in **autonomous mode**. The user has requested minimal interruption.
+
+**Only use the \`${ASK_USER_TOOL_NAME}\` tool if:**
+- A wrong decision would cause significant re-work
+- The request is fundamentally ambiguous with no reasonable default
+- The user explicitly asks you to confirm or ask questions
+
+**Otherwise, work autonomously:**
+- Make reasonable decisions based on context and existing code patterns
+- Follow established project conventions
+- If multiple valid approaches exist, choose the most robust option
+`.trim();
+}
+
 export function renderGitRepo(options?: GitRepoOptions): string {
   if (!options) return '';
   return `
diff --git a/packages/core/src/prompts/snippets.ts b/packages/core/src/prompts/snippets.ts
index 5939722069e..a0614e2aaf6 100644
--- a/packages/core/src/prompts/snippets.ts
+++ b/packages/core/src/prompts/snippets.ts
@@ -33,6 +33,7 @@ export interface SystemPromptOptions {
   planningWorkflow?: PlanningWorkflowOptions;
   operationalGuidelines?: OperationalGuidelinesOptions;
   sandbox?: SandboxMode;
+  interactiveYoloMode?: boolean;
   gitRepo?: GitRepoOptions;
 }
 
@@ -111,6 +112,8 @@ ${
 
 ${renderOperationalGuidelines(options.operationalGuidelines)}
 
+${renderInteractiveYoloMode(options.interactiveYoloMode)}
+
 ${renderSandbox(options.sandbox)}
 
 ${renderGitRepo(options.gitRepo)}
@@ -312,6 +315,25 @@ export function renderSandbox(mode?: SandboxMode): string {
   return '';
 }
 
+export function renderInteractiveYoloMode(enabled?: boolean): string {
+  if (!enabled) return '';
+  return `
+# Autonomous Mode (YOLO)
+
+You are operating in **autonomous mode**. The user has requested minimal interruption.
+
+**Only use the \`${ASK_USER_TOOL_NAME}\` tool if:**
+- A wrong decision would cause significant re-work
+- The request is fundamentally ambiguous with no reasonable default
+- The user explicitly asks you to confirm or ask questions
+
+**Otherwise, work autonomously:**
+- Make reasonable decisions based on context and existing code patterns
+- Follow established project conventions
+- If multiple valid approaches exist, choose the most robust option
+`.trim();
+}
+
 export function renderGitRepo(options?: GitRepoOptions): string {
   if (!options) return '';
   return `