diff --git a/src/capabilities/permissions.test.ts b/src/capabilities/permissions.test.ts
index 53c44393..f046e64e 100644
--- a/src/capabilities/permissions.test.ts
+++ b/src/capabilities/permissions.test.ts
@@ -1,5 +1,5 @@
 import { describe, expect, it } from 'vitest';
-import { splitShellSegments } from './permissions.js';
+import { hasShellRedirection, splitShellSegments } from './permissions.js';
 
 describe('splitShellSegments', () => {
   it('passes simple commands through as a single segment', () => {
@@ -45,3 +45,17 @@ describe('splitShellSegments', () => {
     expect(splitShellSegments('{ reboot now; }')).toEqual(['reboot now']);
   });
 });
+
+describe('hasShellRedirection', () => {
+  it('detects write and heredoc redirections outside quotes', () => {
+    expect(hasShellRedirection('cat README.md > variant.txt')).toBe(true);
+    expect(hasShellRedirection('cat README.md >> variant.txt')).toBe(true);
+    expect(hasShellRedirection('cat <<EOF')).toBe(true);
+  });
+
+  it('ignores literal redirection characters inside quotes or when escaped', () => {
+    expect(hasShellRedirection('echo ">"')).toBe(false);
+    expect(hasShellRedirection("echo '>'")).toBe(false);
+    expect(hasShellRedirection('echo \\> file')).toBe(false);
+  });
+});
diff --git a/src/capabilities/permissions.ts b/src/capabilities/permissions.ts
index c7148b5a..ed04b554 100644
--- a/src/capabilities/permissions.ts
+++ b/src/capabilities/permissions.ts
@@ -280,6 +280,44 @@ export function splitShellSegments(command: string): string[] {
   return out;
 }
 
+export function hasShellRedirection(segment: string): boolean {
+  let single = false;
+  let double = false;
+  let escaped = false;
+
+  for (let i = 0; i < segment.length; i++) {
+    const ch = segment[i];
+    const next = segment[i + 1];
+
+    if (escaped) {
+      escaped = false;
+      continue;
+    }
+
+    if (ch === '\\') {
+      escaped = true;
+      continue;
+    }
+
+    if (!double && ch === "'") {
+      single = !single;
+      continue;
+    }
+
+    if (!single && ch === '"') {
+      double = !double;
+      continue;
+    }
+
+    if (single || double) continue;
+
+    if (ch === '>') return true;
+    if (ch === '<' && next === '<') return true;
+  }
+
+  return false;
+}
+
 export class PermissionManager {
   private manifest: PermissionsManifest;
   private readonly cwd: string;
@@ -502,6 +540,7 @@ export class PermissionManager {
     // Matching the full trimmed string would let `cat foo; rm -rf ~` slip
     // through because `cat *` matches the entire concatenation.
     const allSegmentsSafeRead = segments.length > 0 && segments.every((segment) =>
+      !hasShellRedirection(segment) &&
       PermissionManager.SAFE_READ_PATTERNS.some((p) => this.matchPattern(segment, p))
     );
     if (allSegmentsSafeRead) {