diff --git a/src/workspaces/adapters/ai-config.spec.ts b/src/workspaces/adapters/ai-config.spec.ts
index 6f5f48433..7e1b78600 100644
--- a/src/workspaces/adapters/ai-config.spec.ts
+++ b/src/workspaces/adapters/ai-config.spec.ts
@@ -778,6 +778,46 @@ describe('composeHeadlessCommand (one-shot headless argv, prompt placed per-CLI)
     ]);
   });
 
+  it('claude: a workspace .claude/settings.json permissions.allow widens --allowedTools', async () => {
+    // Claude Code `-p` gates non-safe Bash on the --allowedTools FLAG only, not
+    // on project settings files — so a workspace opts extra command prefixes
+    // into its own headless runs by committing them, and the adapter projects
+    // them onto the flag. Non-Bash/non-mcp entries are dropped.
+    await mkdir(join(dir, '.claude'), { recursive: true });
+    await writeFile(
+      join(dir, '.claude/settings.json'),
+      JSON.stringify({
+        permissions: {
+          allow: [
+            'Bash(bash orb-bot/run_live.sh:*)',
+            'Bash(git push:*)',
+            'mcp__foo__bar',
+            'Read(./secrets)',
+          ],
+        },
+        sandbox: false,
+      }),
+    );
+    const argv = claudeAdapter.composeHeadlessCommand!(['claude'], { cwd: dir, env: {} }, 'do x');
+    const allowed = argv[argv.indexOf('--allowedTools') + 1];
+    expect(allowed).toBe(
+      'Bash(alice:*),Bash(alice-workspace:*),Bash(alice-uta:*),Bash(traderhub:*),'
+      + 'Bash(bash orb-bot/run_live.sh:*),Bash(git push:*),mcp__foo__bar',
+    );
+  });
+
+  it('claude: missing or malformed .claude/settings.json leaves the locked shim list untouched', async () => {
+    const locked = 'Bash(alice:*),Bash(alice-workspace:*),Bash(alice-uta:*),Bash(traderhub:*)';
+    // missing file
+    let argv = claudeAdapter.composeHeadlessCommand!(['claude'], { cwd: dir, env: {} }, 'do x');
+    expect(argv[argv.indexOf('--allowedTools') + 1]).toBe(locked);
+    // malformed file
+    await mkdir(join(dir, '.claude'), { recursive: true });
+    await writeFile(join(dir, '.claude/settings.json'), '{ not json');
+    argv = claudeAdapter.composeHeadlessCommand!(['claude'], { cwd: dir, env: {} }, 'do x');
+    expect(argv[argv.indexOf('--allowedTools') + 1]).toBe(locked);
+  });
+
   it('codex: CLI-mode headless (no MCP) — approval/sandbox/network -c + exec --json -- <prompt>', () => {
     expect(codexAdapter.composeHeadlessCommand!(['codex'], ctx(), 'do x')).toEqual([
       'codex',
diff --git a/src/workspaces/adapters/claude.ts b/src/workspaces/adapters/claude.ts
index 53897f64b..c28c22280 100644
--- a/src/workspaces/adapters/claude.ts
+++ b/src/workspaces/adapters/claude.ts
@@ -1,4 +1,4 @@
-import { createReadStream } from 'node:fs';
+import { createReadStream, readFileSync } from 'node:fs';
 import { readFile, realpath } from 'node:fs/promises';
 import { homedir } from 'node:os';
 import { join, resolve } from 'node:path';
@@ -93,6 +93,34 @@ function isRecord(value: unknown): value is Record<string, unknown> {
   return typeof value === 'object' && value !== null && !Array.isArray(value);
 }
 
+// A workspace may widen its OWN headless Bash surface by committing extra
+// command-prefix rules to `.claude/settings.json` `permissions.allow`. Claude
+// Code `-p` decides non-safe Bash from the `--allowedTools` FLAG only — it does
+// not consult project settings files for that gate (verified 2.1.258) — so a
+// workspace's committed intent has to be projected onto the flag here. The
+// locked shim list above still applies to every workspace that ships no such
+// file. Only `Bash(...)` / `mcp__*` entries are forwarded; a missing or
+// malformed file leaves the default untouched.
+function workspaceHeadlessAllowExtras(cwd: string): string[] {
+  try {
+    const parsed: unknown = JSON.parse(
+      readFileSync(join(cwd, '.claude/settings.json'), 'utf8'),
+    );
+    if (!isRecord(parsed)) return [];
+    const perms = parsed['permissions'];
+    if (!isRecord(perms)) return [];
+    const allow = perms['allow'];
+    if (!Array.isArray(allow)) return [];
+    return allow.filter(
+      (entry): entry is string =>
+        typeof entry === 'string' &&
+        (entry.startsWith('Bash(') || entry.startsWith('mcp__')),
+    );
+  } catch {
+    return [];
+  }
+}
+
 /**
  * Claude Code has two native gates that can consume the first interactive
  * screen before a seeded prompt: global onboarding and per-project trust.
@@ -273,10 +301,14 @@ export const claudeAdapter: CliAdapter = {
     if (ctx.resume === 'last') {
       throw new Error('claude headless: resume requires a concrete resumeId mapping')
     }
+    const allowedTools = [
+      HEADLESS_ALLOWED_TOOLS,
+      ...workspaceHeadlessAllowExtras(ctx.cwd),
+    ].join(',');
     return [
       ...base,
       '--settings', AUTOTRUST_SETTINGS,
-      '--allowedTools', HEADLESS_ALLOWED_TOOLS,
+      '--allowedTools', allowedTools,
       ...(ctx.sessionRuntime?.headlessArgs ?? []),
       ...(ctx.resume ? ['--resume', ctx.resume.sessionId] : []),
       '-p', '--output-format', 'stream-json', '--verbose',