diff --git a/docs/safety.md b/docs/safety.md
index e98d5ecb..c8cb2dd6 100644
--- a/docs/safety.md
+++ b/docs/safety.md
@@ -7,18 +7,18 @@ Loops amplify judgment — good and bad. These guardrails are minimum bar for pr
 The loop must **never** auto-edit these without human approval:
 
 ```
-.env
-.env.*
+**/.env
+**/.env.*
 **/secrets/**
 **/credentials/**
 **/*_key*
 **/*_secret*
-.terraform/**
-k8s/production/**
+**/.terraform/**
+**/k8s/production/**
 **/migrations/**          # unless explicit migration loop
-auth/**
-payments/**
-billing/**
+**/auth/**
+**/payments/**
+**/billing/**
 ```
 
 Encode in `minimal-fix` and implementer skills:
diff --git a/gate.yaml b/gate.yaml
index 60da1653..976f4b74 100644
--- a/gate.yaml
+++ b/gate.yaml
@@ -4,18 +4,18 @@
 version: 1
 
 denylist:
-  - ".env"
-  - ".env.*"
+  - "**/.env"
+  - "**/.env.*"
   - "**/secrets/**"
   - "**/credentials/**"
   - "**/*_key*"
   - "**/*_secret*"
-  - ".terraform/**"
-  - "k8s/production/**"
+  - "**/.terraform/**"
+  - "**/k8s/production/**"
   - "**/migrations/**"
-  - "auth/**"
-  - "payments/**"
-  - "billing/**"
+  - "**/auth/**"
+  - "**/payments/**"
+  - "**/billing/**"
 
 maxFiles: 10
 
diff --git a/templates/gate.yaml.template b/templates/gate.yaml.template
index 0eb433fa..2f348927 100644
--- a/templates/gate.yaml.template
+++ b/templates/gate.yaml.template
@@ -5,18 +5,18 @@
 version: 1
 
 denylist:
-  - ".env"
-  - ".env.*"
+  - "**/.env"
+  - "**/.env.*"
   - "**/secrets/**"
   - "**/credentials/**"
   - "**/*_key*"
   - "**/*_secret*"
-  - ".terraform/**"
-  - "k8s/production/**"
+  - "**/.terraform/**"
+  - "**/k8s/production/**"
   - "**/migrations/**"
-  - "auth/**"
-  - "payments/**"
-  - "billing/**"
+  - "**/auth/**"
+  - "**/payments/**"
+  - "**/billing/**"
 
 # Escalate instead of auto-merging when a change touches more than this many files.
 maxFiles: 10
diff --git a/tools/loop-audit/dist/autofixer.js b/tools/loop-audit/dist/autofixer.js
index 6cafa8dd..c0b4cb27 100644
--- a/tools/loop-audit/dist/autofixer.js
+++ b/tools/loop-audit/dist/autofixer.js
@@ -152,8 +152,8 @@ const GATE_YAML_TEMPLATE = `# Machine-readable twin of docs/safety.md, enforced
 version: 1
 
 denylist:
-  - ".env"
-  - ".env.*"
+  - "**/.env"
+  - "**/.env.*"
   - "**/secrets/**"
   - "**/credentials/**"
   - "**/*_key*"
diff --git a/tools/loop-audit/src/autofixer.ts b/tools/loop-audit/src/autofixer.ts
index 48f45e05..aba5662e 100644
--- a/tools/loop-audit/src/autofixer.ts
+++ b/tools/loop-audit/src/autofixer.ts
@@ -161,8 +161,8 @@ const GATE_YAML_TEMPLATE = `# Machine-readable twin of docs/safety.md, enforced
 version: 1
 
 denylist:
-  - ".env"
-  - ".env.*"
+  - "**/.env"
+  - "**/.env.*"
   - "**/secrets/**"
   - "**/credentials/**"
   - "**/*_key*"
diff --git a/tools/loop-audit/test/autofixer.test.mjs b/tools/loop-audit/test/autofixer.test.mjs
index 862f7b97..3111e211 100644
--- a/tools/loop-audit/test/autofixer.test.mjs
+++ b/tools/loop-audit/test/autofixer.test.mjs
@@ -46,6 +46,21 @@ test('autoFixProject writes a gate.yaml that loop-gate can actually load', async
     assert.match(written, /version:\s*1/);
     assert.match(written, /denylist:/);
     assert.doesNotMatch(written, /^gates:/m);
+
+    // A bare pattern like ".env" only matches a path exactly equal to
+    // ".env" under minimatch -- it silently misses "services/api/.env".
+    // Every denylist entry here must be **/-anchored (or already contain
+    // its own ** segment) so it also catches the nested case, which is
+    // what "never auto-edit these" in docs/safety.md actually means.
+    const denylistBlock = written.match(/denylist:\n((?:\s+-\s+.+\n)+)/)?.[1] ?? '';
+    const entries = [...denylistBlock.matchAll(/-\s+"([^"]+)"/g)].map((m) => m[1]);
+    assert.ok(entries.length > 0, 'expected at least one denylist entry to check');
+    for (const entry of entries) {
+      assert.ok(
+        entry.startsWith('**/') || entry.includes('**'),
+        `denylist entry "${entry}" is not anchored and would miss a nested match`,
+      );
+    }
   } finally {
     await rm(root, { recursive: true, force: true }).catch(() => {});
   }
diff --git a/tools/loop-gate/test/gate.test.mjs b/tools/loop-gate/test/gate.test.mjs
index abb1103f..4a66d8ca 100644
--- a/tools/loop-gate/test/gate.test.mjs
+++ b/tools/loop-gate/test/gate.test.mjs
@@ -3,9 +3,13 @@ import assert from 'node:assert/strict';
 import { mkdtemp, writeFile } from 'node:fs/promises';
 import { tmpdir } from 'node:os';
 import path from 'node:path';
+import { fileURLToPath } from 'node:url';
 
 import { checkGate, loadGateConfig, assertValidAction } from '../dist/gate.js';
 
+const __dirname = path.dirname(fileURLToPath(import.meta.url));
+const REPO_GATE_YAML = path.resolve(__dirname, '../../../gate.yaml');
+
 const baseConfig = {
   version: 1,
   denylist: ['.env', '**/secrets/**', 'auth/**'],
@@ -143,3 +147,26 @@ test('loadGateConfig rejects the wrong version', async () => {
   const file = await freshGateFile('version: 2\ndenylist: []\n');
   await assert.rejects(() => loadGateConfig(file), /Invalid gate config/);
 });
+
+// Dogfoods the actual policy this repo ships at gate.yaml, not just the
+// matching mechanism -- a bare (unanchored) pattern like ".env" or "auth/**"
+// only matches that exact root-level path and silently misses the same
+// file/dir nested anywhere else, which a schema-validity check alone would
+// never catch.
+test("this repo's own gate.yaml denylist catches sensitive paths nested in a subdirectory, not just at repo root", async () => {
+  const config = await loadGateConfig(REPO_GATE_YAML);
+  const nestedSensitivePaths = [
+    'services/api/.env',
+    'services/api/.env.production',
+    'infra/.terraform/state.tfstate',
+    'apps/backend/k8s/production/deploy.yaml',
+    'apps/backend/auth/session.ts',
+    'apps/checkout/payments/charge.ts',
+    'apps/checkout/billing/invoice.ts',
+  ];
+  for (const p of nestedSensitivePaths) {
+    const decision = checkGate({ config, action: 'commit', paths: [p] });
+    assert.equal(decision.allowed, false, `${p} should be denylisted, got: ${decision.reason}`);
+    assert.equal(decision.trigger, 'denylist');
+  }
+});
diff --git a/tools/loop-sync/dist/sync.js b/tools/loop-sync/dist/sync.js
index d9900dae..304255f8 100644
--- a/tools/loop-sync/dist/sync.js
+++ b/tools/loop-sync/dist/sync.js
@@ -162,18 +162,18 @@ Run log: (timestamp) | findings | actions | escalations
 version: 1
 
 denylist:
-  - ".env"
-  - ".env.*"
+  - "**/.env"
+  - "**/.env.*"
   - "**/secrets/**"
   - "**/credentials/**"
   - "**/*_key*"
   - "**/*_secret*"
-  - ".terraform/**"
-  - "k8s/production/**"
+  - "**/.terraform/**"
+  - "**/k8s/production/**"
   - "**/migrations/**"
-  - "auth/**"
-  - "payments/**"
-  - "billing/**"
+  - "**/auth/**"
+  - "**/payments/**"
+  - "**/billing/**"
 
 # Escalate instead of auto-merging when a change touches more than this many files.
 maxFiles: 10
diff --git a/tools/loop-sync/src/sync.ts b/tools/loop-sync/src/sync.ts
index f0567f64..12238e55 100644
--- a/tools/loop-sync/src/sync.ts
+++ b/tools/loop-sync/src/sync.ts
@@ -210,18 +210,18 @@ Run log: (timestamp) | findings | actions | escalations
 version: 1
 
 denylist:
-  - ".env"
-  - ".env.*"
+  - "**/.env"
+  - "**/.env.*"
   - "**/secrets/**"
   - "**/credentials/**"
   - "**/*_key*"
   - "**/*_secret*"
-  - ".terraform/**"
-  - "k8s/production/**"
+  - "**/.terraform/**"
+  - "**/k8s/production/**"
   - "**/migrations/**"
-  - "auth/**"
-  - "payments/**"
-  - "billing/**"
+  - "**/auth/**"
+  - "**/payments/**"
+  - "**/billing/**"
 
 # Escalate instead of auto-merging when a change touches more than this many files.
 maxFiles: 10
diff --git a/tools/loop-sync/test/sync.test.mjs b/tools/loop-sync/test/sync.test.mjs
index b649b5a1..1e56cce0 100644
--- a/tools/loop-sync/test/sync.test.mjs
+++ b/tools/loop-sync/test/sync.test.mjs
@@ -102,6 +102,22 @@ describe('runSync auto-fix', () => {
     // loop-run-log.md must keep the marker append-run-log.mjs depends on.
     const runLog = await readFile(path.join(fixDir, 'loop-run-log.md'), 'utf8');
     assert.match(runLog, /<!-- Loop appends below this line -->/);
+
+    // A bare pattern like ".env" only matches a path exactly equal to
+    // ".env" under minimatch (tools/loop-gate's matcher) -- it silently
+    // misses "services/api/.env". Every denylist entry must be
+    // **/-anchored (or already contain its own ** segment) so the
+    // scaffolded policy actually catches a nested match too.
+    const gateYaml = await readFile(path.join(fixDir, 'gate.yaml'), 'utf8');
+    const denylistBlock = gateYaml.match(/denylist:\n((?:\s+-\s+.+\n)+)/)?.[1] ?? '';
+    const entries = [...denylistBlock.matchAll(/-\s+"([^"]+)"/g)].map((m) => m[1]);
+    assert.ok(entries.length > 0, 'expected at least one denylist entry to check');
+    for (const entry of entries) {
+      assert.ok(
+        entry.startsWith('**/') || entry.includes('**'),
+        `denylist entry "${entry}" is not anchored and would miss a nested match`,
+      );
+    }
   });
 
   test('does not fabricate LOOP.md or AGENTS.md -- still reported as missing', async () => {