diff --git a/.gitignore b/.gitignore
index 04385494854..119f9311f3a 100644
--- a/.gitignore
+++ b/.gitignore
@@ -61,4 +61,10 @@ gemini-debug.log
 .genkit
 .gemini-clipboard/
 .eslintcache
-evals/logs/
\ No newline at end of file
+evals/logs/
+
+# Generated output and declaration files
+*.txt
+!NOTICES.txt
+!LICENSE.txt
+packages/*/src/**/*.d.ts
\ No newline at end of file
diff --git a/integration-tests/policy_repro.responses b/integration-tests/policy_repro.responses
new file mode 100644
index 00000000000..155d92eeacf
--- /dev/null
+++ b/integration-tests/policy_repro.responses
@@ -0,0 +1,2 @@
+{"method":"generateContentStream","response":[{"candidates":[{"content":{"parts":[{"functionCall":{"name":"run_shell_command","args":{"command":"echo policy-test-passed"}}}]},"finishReason":"STOP","index":0}]}]}
+{"method":"generateContentStream","response":[{"candidates":[{"content":{"parts":[{"text":"I was unable to run the command because it was blocked by policy."}]},"finishReason":"STOP","index":0}]}]}
diff --git a/integration-tests/policy_repro.test.ts b/integration-tests/policy_repro.test.ts
new file mode 100644
index 00000000000..581ee1e49eb
--- /dev/null
+++ b/integration-tests/policy_repro.test.ts
@@ -0,0 +1,148 @@
+/**
+ * @license
+ * Copyright 2025 Google LLC
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+import { describe, it, expect, beforeEach, afterEach, vi } from 'vitest';
+import { TestRig, printDebugInfo } from './test-helper.js';
+import * as path from 'node:path';
+
+describe('Headless Policy Reproduction', () => {
+  let rig: TestRig;
+
+  beforeEach(() => {
+    rig = new TestRig();
+    vi.stubEnv('GEMINI_API_KEY', 'fake-key');
+  });
+
+  afterEach(async () => {
+    await rig.cleanup();
+    vi.unstubAllEnvs();
+  });
+
+  it('should block tools that require ask_user confirmation in headless mode', async () => {
+    // 1. Setup the rig with fake responses
+    const responsesPath = path.resolve(__dirname, 'policy_repro.responses');
+    await rig.setup(
+      'should block tools that require ask_user confirmation in headless mode',
+      {
+        fakeResponsesPath: responsesPath,
+        settings: {
+          model: {
+            name: 'gemini-1.5-pro',
+          },
+        },
+      },
+    );
+
+    // 2. Create a policy file with ask_user for run_shell_command.
+    // In headless/non-interactive mode, ask_user decisions must be converted to DENY,
+    // preventing the tool from executing.
+    const policyContent = `
+[[rule]]
+toolName = "run_shell_command"
+decision = "ask_user"
+priority = 999
+    `;
+    const policyPath = rig.createFile('ask-shell.toml', policyContent);
+    const prompt = 'Run "echo policy-test-passed" and show me the output';
+
+    const result = await rig.run({
+      args: ['-p', prompt, '--policy', policyPath],
+      env: {
+        GEMINI_DEBUG: '1',
+        VERBOSE: 'true',
+      },
+    });
+
+    // 3. Wait for any tool call attempt (the tool will be attempted but should fail with error).
+    // waitForToolCall returns true even for failed/errored calls.
+    await rig.waitForToolCall('run_shell_command');
+
+    // 4. Check the tool call was NOT successful.
+    const toolLogs = rig.readToolLogs();
+    const shellCommandLog = toolLogs.find(
+      (log) => log.toolRequest.name === 'run_shell_command',
+    );
+
+    if (!shellCommandLog || shellCommandLog.toolRequest.success) {
+      console.log('CLI Result:', result);
+      printDebugInfo(rig, result, {
+        'Tool log entry': shellCommandLog,
+        'Policy path': policyPath,
+        'Result contains blocked string': result.includes('policy-test-passed'),
+      });
+    }
+
+    // The tool call should have been attempted but blocked (not successful).
+    expect(
+      shellCommandLog?.toolRequest.success,
+      'Expected run_shell_command to be BLOCKED by policy in headless mode (success should be false)',
+    ).toBe(false);
+
+    // The actual command result should not appear in the output.
+    expect(result).not.toContain('policy-test-passed');
+  }, 15000);
+
+  it('should treat global ask_user decisions as DENY in headless mode', async () => {
+    // 1. Setup the rig with fake responses
+    const responsesPath = path.resolve(__dirname, 'policy_repro.responses');
+    await rig.setup(
+      'should treat global ask_user decisions as DENY in headless mode',
+      {
+        fakeResponsesPath: responsesPath,
+        settings: {
+          model: {
+            name: 'gemini-1.5-pro',
+          },
+        },
+      },
+    );
+
+    // 2. Create a global policy file with ask_user.
+    // In headless/non-interactive mode, ask_user decisions must be converted to DENY.
+    const policyContent = `
+[[rule]]
+decision = "ask_user"
+priority = 999
+    `;
+    const policyPath = rig.createFile('global-ask.toml', policyContent);
+    const prompt = 'Run "echo global-test-passed" and show me the output';
+
+    const result = await rig.run({
+      args: ['-p', prompt, '--policy', policyPath],
+      env: {
+        GEMINI_DEBUG: '1',
+        VERBOSE: 'true',
+      },
+    });
+
+    // 3. Wait for any tool call attempt.
+    await rig.waitForToolCall('run_shell_command');
+
+    // 4. Check the tool call was NOT successful.
+    const toolLogs = rig.readToolLogs();
+    const shellCommandLog = toolLogs.find(
+      (log) => log.toolRequest.name === 'run_shell_command',
+    );
+
+    if (!shellCommandLog || shellCommandLog.toolRequest.success) {
+      console.log('CLI Result:', result);
+      printDebugInfo(rig, result, {
+        'Tool log entry': shellCommandLog,
+        'Policy path': policyPath,
+        'Result contains blocked string': result.includes('global-test-passed'),
+      });
+    }
+
+    // The tool call should have been attempted but blocked (not successful).
+    expect(
+      shellCommandLog?.toolRequest.success,
+      'Expected run_shell_command to be BLOCKED by global policy in headless mode (success should be false)',
+    ).toBe(false);
+
+    // The actual command result should not appear in the output.
+    expect(result).not.toContain('global-test-passed');
+  }, 15000);
+});
diff --git a/package-lock.json b/package-lock.json
index 82bf1c22216..33016dffc7f 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -1079,9 +1079,9 @@
       }
     },
     "node_modules/@eslint/config-array/node_modules/minimatch": {
-      "version": "10.2.2",
-      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.2.2.tgz",
-      "integrity": "sha512-+G4CpNBxa5MprY+04MbgOw1v7So6n5JY166pFi9KfYwT78fxScCeSNQSNzp6dpPSW2rONOps6Ocam1wFhCgoVw==",
+      "version": "10.2.4",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.2.4.tgz",
+      "integrity": "sha512-oRjTw/97aTBN0RHbYCdtF1MQfvusSIBQM0IZEgzl6426+8jSC0nF1a/GmnVLpfB9yyr6g6FTqWqiZVbxrtaCIg==",
       "dev": true,
       "license": "BlueOak-1.0.0",
       "dependencies": {
@@ -1181,9 +1181,9 @@
       }
     },
     "node_modules/@eslint/eslintrc/node_modules/minimatch": {
-      "version": "10.2.2",
-      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.2.2.tgz",
-      "integrity": "sha512-+G4CpNBxa5MprY+04MbgOw1v7So6n5JY166pFi9KfYwT78fxScCeSNQSNzp6dpPSW2rONOps6Ocam1wFhCgoVw==",
+      "version": "10.2.4",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.2.4.tgz",
+      "integrity": "sha512-oRjTw/97aTBN0RHbYCdtF1MQfvusSIBQM0IZEgzl6426+8jSC0nF1a/GmnVLpfB9yyr6g6FTqWqiZVbxrtaCIg==",
       "dev": true,
       "license": "BlueOak-1.0.0",
       "dependencies": {
@@ -3130,9 +3130,9 @@
       "license": "BSD-3-Clause"
     },
     "node_modules/@rollup/rollup-android-arm-eabi": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-android-arm-eabi/-/rollup-android-arm-eabi-4.53.2.tgz",
-      "integrity": "sha512-yDPzwsgiFO26RJA4nZo8I+xqzh7sJTZIWQOxn+/XOdPE31lAvLIYCKqjV+lNH/vxE2L2iH3plKxDCRK6i+CwhA==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-android-arm-eabi/-/rollup-android-arm-eabi-4.59.0.tgz",
+      "integrity": "sha512-upnNBkA6ZH2VKGcBj9Fyl9IGNPULcjXRlg0LLeaioQWueH30p6IXtJEbKAgvyv+mJaMxSm1l6xwDXYjpEMiLMg==",
       "cpu": [
         "arm"
       ],
@@ -3143,9 +3143,9 @@
       ]
     },
     "node_modules/@rollup/rollup-android-arm64": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-android-arm64/-/rollup-android-arm64-4.53.2.tgz",
-      "integrity": "sha512-k8FontTxIE7b0/OGKeSN5B6j25EuppBcWM33Z19JoVT7UTXFSo3D9CdU39wGTeb29NO3XxpMNauh09B+Ibw+9g==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-android-arm64/-/rollup-android-arm64-4.59.0.tgz",
+      "integrity": "sha512-hZ+Zxj3SySm4A/DylsDKZAeVg0mvi++0PYVceVyX7hemkw7OreKdCvW2oQ3T1FMZvCaQXqOTHb8qmBShoqk69Q==",
       "cpu": [
         "arm64"
       ],
@@ -3156,9 +3156,9 @@
       ]
     },
     "node_modules/@rollup/rollup-darwin-arm64": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-darwin-arm64/-/rollup-darwin-arm64-4.53.2.tgz",
-      "integrity": "sha512-A6s4gJpomNBtJ2yioj8bflM2oogDwzUiMl2yNJ2v9E7++sHrSrsQ29fOfn5DM/iCzpWcebNYEdXpaK4tr2RhfQ==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-darwin-arm64/-/rollup-darwin-arm64-4.59.0.tgz",
+      "integrity": "sha512-W2Psnbh1J8ZJw0xKAd8zdNgF9HRLkdWwwdWqubSVk0pUuQkoHnv7rx4GiF9rT4t5DIZGAsConRE3AxCdJ4m8rg==",
       "cpu": [
         "arm64"
       ],
@@ -3169,9 +3169,9 @@
       ]
     },
     "node_modules/@rollup/rollup-darwin-x64": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-darwin-x64/-/rollup-darwin-x64-4.53.2.tgz",
-      "integrity": "sha512-e6XqVmXlHrBlG56obu9gDRPW3O3hLxpwHpLsBJvuI8qqnsrtSZ9ERoWUXtPOkY8c78WghyPHZdmPhHLWNdAGEw==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-darwin-x64/-/rollup-darwin-x64-4.59.0.tgz",
+      "integrity": "sha512-ZW2KkwlS4lwTv7ZVsYDiARfFCnSGhzYPdiOU4IM2fDbL+QGlyAbjgSFuqNRbSthybLbIJ915UtZBtmuLrQAT/w==",
       "cpu": [
         "x64"
       ],
@@ -3182,9 +3182,9 @@
       ]
     },
     "node_modules/@rollup/rollup-freebsd-arm64": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-freebsd-arm64/-/rollup-freebsd-arm64-4.53.2.tgz",
-      "integrity": "sha512-v0E9lJW8VsrwPux5Qe5CwmH/CF/2mQs6xU1MF3nmUxmZUCHazCjLgYvToOk+YuuUqLQBio1qkkREhxhc656ViA==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-freebsd-arm64/-/rollup-freebsd-arm64-4.59.0.tgz",
+      "integrity": "sha512-EsKaJ5ytAu9jI3lonzn3BgG8iRBjV4LxZexygcQbpiU0wU0ATxhNVEpXKfUa0pS05gTcSDMKpn3Sx+QB9RlTTA==",
       "cpu": [
         "arm64"
       ],
@@ -3195,9 +3195,9 @@
       ]
     },
     "node_modules/@rollup/rollup-freebsd-x64": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-freebsd-x64/-/rollup-freebsd-x64-4.53.2.tgz",
-      "integrity": "sha512-ClAmAPx3ZCHtp6ysl4XEhWU69GUB1D+s7G9YjHGhIGCSrsg00nEGRRZHmINYxkdoJehde8VIsDC5t9C0gb6yqA==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-freebsd-x64/-/rollup-freebsd-x64-4.59.0.tgz",
+      "integrity": "sha512-d3DuZi2KzTMjImrxoHIAODUZYoUUMsuUiY4SRRcJy6NJoZ6iIqWnJu9IScV9jXysyGMVuW+KNzZvBLOcpdl3Vg==",
       "cpu": [
         "x64"
       ],
@@ -3208,9 +3208,9 @@
       ]
     },
     "node_modules/@rollup/rollup-linux-arm-gnueabihf": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-arm-gnueabihf/-/rollup-linux-arm-gnueabihf-4.53.2.tgz",
-      "integrity": "sha512-EPlb95nUsz6Dd9Qy13fI5kUPXNSljaG9FiJ4YUGU1O/Q77i5DYFW5KR8g1OzTcdZUqQQ1KdDqsTohdFVwCwjqg==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-arm-gnueabihf/-/rollup-linux-arm-gnueabihf-4.59.0.tgz",
+      "integrity": "sha512-t4ONHboXi/3E0rT6OZl1pKbl2Vgxf9vJfWgmUoCEVQVxhW6Cw/c8I6hbbu7DAvgp82RKiH7TpLwxnJeKv2pbsw==",
       "cpu": [
         "arm"
       ],
@@ -3221,9 +3221,9 @@
       ]
     },
     "node_modules/@rollup/rollup-linux-arm-musleabihf": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-arm-musleabihf/-/rollup-linux-arm-musleabihf-4.53.2.tgz",
-      "integrity": "sha512-BOmnVW+khAUX+YZvNfa0tGTEMVVEerOxN0pDk2E6N6DsEIa2Ctj48FOMfNDdrwinocKaC7YXUZ1pHlKpnkja/Q==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-arm-musleabihf/-/rollup-linux-arm-musleabihf-4.59.0.tgz",
+      "integrity": "sha512-CikFT7aYPA2ufMD086cVORBYGHffBo4K8MQ4uPS/ZnY54GKj36i196u8U+aDVT2LX4eSMbyHtyOh7D7Zvk2VvA==",
       "cpu": [
         "arm"
       ],
@@ -3234,9 +3234,9 @@
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     },
     "node_modules/@rollup/rollup-linux-arm64-gnu": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-arm64-gnu/-/rollup-linux-arm64-gnu-4.53.2.tgz",
-      "integrity": "sha512-Xt2byDZ+6OVNuREgBXr4+CZDJtrVso5woFtpKdGPhpTPHcNG7D8YXeQzpNbFRxzTVqJf7kvPMCub/pcGUWgBjA==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-arm64-gnu/-/rollup-linux-arm64-gnu-4.59.0.tgz",
+      "integrity": "sha512-jYgUGk5aLd1nUb1CtQ8E+t5JhLc9x5WdBKew9ZgAXg7DBk0ZHErLHdXM24rfX+bKrFe+Xp5YuJo54I5HFjGDAA==",
       "cpu": [
         "arm64"
       ],
@@ -3247,9 +3247,9 @@
       ]
     },
     "node_modules/@rollup/rollup-linux-arm64-musl": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-arm64-musl/-/rollup-linux-arm64-musl-4.53.2.tgz",
-      "integrity": "sha512-+LdZSldy/I9N8+klim/Y1HsKbJ3BbInHav5qE9Iy77dtHC/pibw1SR/fXlWyAk0ThnpRKoODwnAuSjqxFRDHUQ==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-arm64-musl/-/rollup-linux-arm64-musl-4.59.0.tgz",
+      "integrity": "sha512-peZRVEdnFWZ5Bh2KeumKG9ty7aCXzzEsHShOZEFiCQlDEepP1dpUl/SrUNXNg13UmZl+gzVDPsiCwnV1uI0RUA==",
       "cpu": [
         "arm64"
       ],
@@ -3260,9 +3260,22 @@
       ]
     },
     "node_modules/@rollup/rollup-linux-loong64-gnu": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-loong64-gnu/-/rollup-linux-loong64-gnu-4.53.2.tgz",
-      "integrity": "sha512-8ms8sjmyc1jWJS6WdNSA23rEfdjWB30LH8Wqj0Cqvv7qSHnvw6kgMMXRdop6hkmGPlyYBdRPkjJnj3KCUHV/uQ==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-loong64-gnu/-/rollup-linux-loong64-gnu-4.59.0.tgz",
+      "integrity": "sha512-gbUSW/97f7+r4gHy3Jlup8zDG190AuodsWnNiXErp9mT90iCy9NKKU0Xwx5k8VlRAIV2uU9CsMnEFg/xXaOfXg==",
+      "cpu": [
+        "loong64"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "linux"
+      ]
+    },
+    "node_modules/@rollup/rollup-linux-loong64-musl": {
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-loong64-musl/-/rollup-linux-loong64-musl-4.59.0.tgz",
+      "integrity": "sha512-yTRONe79E+o0FWFijasoTjtzG9EBedFXJMl888NBEDCDV9I2wGbFFfJQQe63OijbFCUZqxpHz1GzpbtSFikJ4Q==",
       "cpu": [
         "loong64"
       ],
@@ -3273,9 +3286,22 @@
       ]
     },
     "node_modules/@rollup/rollup-linux-ppc64-gnu": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-ppc64-gnu/-/rollup-linux-ppc64-gnu-4.53.2.tgz",
-      "integrity": "sha512-3HRQLUQbpBDMmzoxPJYd3W6vrVHOo2cVW8RUo87Xz0JPJcBLBr5kZ1pGcQAhdZgX9VV7NbGNipah1omKKe23/g==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-ppc64-gnu/-/rollup-linux-ppc64-gnu-4.59.0.tgz",
+      "integrity": "sha512-sw1o3tfyk12k3OEpRddF68a1unZ5VCN7zoTNtSn2KndUE+ea3m3ROOKRCZxEpmT9nsGnogpFP9x6mnLTCaoLkA==",
+      "cpu": [
+        "ppc64"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "linux"
+      ]
+    },
+    "node_modules/@rollup/rollup-linux-ppc64-musl": {
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-ppc64-musl/-/rollup-linux-ppc64-musl-4.59.0.tgz",
+      "integrity": "sha512-+2kLtQ4xT3AiIxkzFVFXfsmlZiG5FXYW7ZyIIvGA7Bdeuh9Z0aN4hVyXS/G1E9bTP/vqszNIN/pUKCk/BTHsKA==",
       "cpu": [
         "ppc64"
       ],
@@ -3286,9 +3312,9 @@
       ]
     },
     "node_modules/@rollup/rollup-linux-riscv64-gnu": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-riscv64-gnu/-/rollup-linux-riscv64-gnu-4.53.2.tgz",
-      "integrity": "sha512-fMjKi+ojnmIvhk34gZP94vjogXNNUKMEYs+EDaB/5TG/wUkoeua7p7VCHnE6T2Tx+iaghAqQX8teQzcvrYpaQA==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-riscv64-gnu/-/rollup-linux-riscv64-gnu-4.59.0.tgz",
+      "integrity": "sha512-NDYMpsXYJJaj+I7UdwIuHHNxXZ/b/N2hR15NyH3m2qAtb/hHPA4g4SuuvrdxetTdndfj9b1WOmy73kcPRoERUg==",
       "cpu": [
         "riscv64"
       ],
@@ -3299,9 +3325,9 @@
       ]
     },
     "node_modules/@rollup/rollup-linux-riscv64-musl": {
-      "version": "4.53.2",
-      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-riscv64-musl/-/rollup-linux-riscv64-musl-4.53.2.tgz",
-      "integrity": "sha512-XuGFGU+VwUUV5kLvoAdi0Wz5Xbh2SrjIxCtZj6Wq8MDp4bflb/+ThZsVxokM7n0pcbkEr2h5/pzqzDYI7cCgLQ==",
+      "version": "4.59.0",
+      "resolved": "https://registry.npmjs.org/@rollup/rollup-linux-riscv64-musl/-/rollup-linux-riscv64-musl-4.59.0.tgz",
+      "integrity": "sha512-nLckB8WOqHIf1bhymk+oHxvM9D3tyPndZH8i8+35p/1YiVoVswPid2yLzgX7ZJP0KQvnkhM4H6QZ5m0LzbyIAg==",
       "cpu": [
         "riscv64"
       ],
@@ -3312,9 +3338,9 @@
       ]
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+        "@rollup/rollup-android-arm64": "4.59.0",
+        "@rollup/rollup-darwin-arm64": "4.59.0",
+        "@rollup/rollup-darwin-x64": "4.59.0",
+        "@rollup/rollup-freebsd-arm64": "4.59.0",
+        "@rollup/rollup-freebsd-x64": "4.59.0",
+        "@rollup/rollup-linux-arm-gnueabihf": "4.59.0",
+        "@rollup/rollup-linux-arm-musleabihf": "4.59.0",
+        "@rollup/rollup-linux-arm64-gnu": "4.59.0",
+        "@rollup/rollup-linux-arm64-musl": "4.59.0",
+        "@rollup/rollup-linux-loong64-gnu": "4.59.0",
+        "@rollup/rollup-linux-loong64-musl": "4.59.0",
+        "@rollup/rollup-linux-ppc64-gnu": "4.59.0",
+        "@rollup/rollup-linux-ppc64-musl": "4.59.0",
+        "@rollup/rollup-linux-riscv64-gnu": "4.59.0",
+        "@rollup/rollup-linux-riscv64-musl": "4.59.0",
+        "@rollup/rollup-linux-s390x-gnu": "4.59.0",
+        "@rollup/rollup-linux-x64-gnu": "4.59.0",
+        "@rollup/rollup-linux-x64-musl": "4.59.0",
+        "@rollup/rollup-openbsd-x64": "4.59.0",
+        "@rollup/rollup-openharmony-arm64": "4.59.0",
+        "@rollup/rollup-win32-arm64-msvc": "4.59.0",
+        "@rollup/rollup-win32-ia32-msvc": "4.59.0",
+        "@rollup/rollup-win32-x64-gnu": "4.59.0",
+        "@rollup/rollup-win32-x64-msvc": "4.59.0",
         "fsevents": "~2.3.2"
       }
     },
@@ -15557,9 +15612,9 @@
       }
     },
     "node_modules/test-exclude/node_modules/minimatch": {
-      "version": "10.2.2",
-      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.2.2.tgz",
-      "integrity": "sha512-+G4CpNBxa5MprY+04MbgOw1v7So6n5JY166pFi9KfYwT78fxScCeSNQSNzp6dpPSW2rONOps6Ocam1wFhCgoVw==",
+      "version": "10.2.4",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.2.4.tgz",
+      "integrity": "sha512-oRjTw/97aTBN0RHbYCdtF1MQfvusSIBQM0IZEgzl6426+8jSC0nF1a/GmnVLpfB9yyr6g6FTqWqiZVbxrtaCIg==",
       "dev": true,
       "license": "BlueOak-1.0.0",
       "dependencies": {
diff --git a/packages/core/src/policy/policy-engine.test.ts b/packages/core/src/policy/policy-engine.test.ts
index f93c9ad3b85..dbb0f00c410 100644
--- a/packages/core/src/policy/policy-engine.test.ts
+++ b/packages/core/src/policy/policy-engine.test.ts
@@ -2223,7 +2223,7 @@ describe('PolicyEngine', () => {
         expected: [],
       },
       {
-        name: 'should NOT include ASK_USER tools even in non-interactive mode',
+        name: 'should include ASK_USER tools in non-interactive mode',
         rules: [
           {
             toolName: 'tool1',
@@ -2232,6 +2232,18 @@ describe('PolicyEngine', () => {
           },
         ],
         nonInteractive: true,
+        expected: ['tool1'],
+      },
+      {
+        name: 'should NOT exclude ASK_USER tools in interactive mode',
+        rules: [
+          {
+            toolName: 'tool1',
+            decision: PolicyDecision.ASK_USER,
+            modes: [ApprovalMode.DEFAULT],
+          },
+        ],
+        nonInteractive: false,
         expected: [],
       },
       {
diff --git a/packages/core/src/policy/policy-engine.ts b/packages/core/src/policy/policy-engine.ts
index 03087716ffd..bd7aa464404 100644
--- a/packages/core/src/policy/policy-engine.ts
+++ b/packages/core/src/policy/policy-engine.ts
@@ -657,9 +657,24 @@ export class PolicyEngine {
     const processedTools = new Set<string>();
     let globalVerdict: PolicyDecision | undefined;
 
+    const normalizeDecision = (
+      decision: PolicyDecision,
+      isHeadless: boolean,
+    ): PolicyDecision => {
+      if (isHeadless && decision === PolicyDecision.ASK_USER) {
+        return PolicyDecision.DENY;
+      }
+      return decision;
+    };
+
     for (const rule of this.rules) {
+      const normalizedDecision = normalizeDecision(
+        rule.decision,
+        this.nonInteractive,
+      );
+
       if (rule.argsPattern) {
-        if (rule.toolName && rule.decision !== PolicyDecision.DENY) {
+        if (rule.toolName && normalizedDecision !== PolicyDecision.DENY) {
           processedTools.add(rule.toolName);
         }
         continue;
@@ -718,7 +733,7 @@ export class PolicyEngine {
           if (globalVerdict !== undefined) {
             decision = globalVerdict;
           } else {
-            decision = rule.decision;
+            decision = normalizedDecision;
           }
           if (decision === PolicyDecision.DENY) {
             excludedTools.add(toolName);
@@ -731,7 +746,7 @@ export class PolicyEngine {
       // Handle Global Rules
       if (!rule.toolName) {
         if (globalVerdict === undefined) {
-          globalVerdict = rule.decision;
+          globalVerdict = normalizedDecision;
           if (globalVerdict !== PolicyDecision.DENY) {
             // Global ALLOW/ASK found.
             // Since rules are sorted by priority, this overrides any lower-priority rules.
@@ -777,7 +792,7 @@ export class PolicyEngine {
       if (globalVerdict !== undefined) {
         decision = globalVerdict;
       } else {
-        decision = rule.decision;
+        decision = normalizedDecision;
       }
 
       if (decision === PolicyDecision.DENY) {