diff --git a/manifests/context-packs/skill-triggers@1.json b/manifests/context-packs/skill-triggers@1.json
index f529c8350..ead361dd7 100644
--- a/manifests/context-packs/skill-triggers@1.json
+++ b/manifests/context-packs/skill-triggers@1.json
@@ -10,7 +10,7 @@
     "id": "hand-seeded",
     "source": "manual-curation-pending-regeneration"
   },
-  "registryDigest": "62dc25b99e2b6ccd60a22014d9c75f9a98cb89ffd6870a4e7d32e653b76e0e63",
+  "registryDigest": "2c1024b127b18808916ac0d31037bc1a90c7c1c8df8021d0882dbe2273ae02fe",
   "schemaVersion": 1,
   "triggers": {
     "skill:agent-runtime-gateway-smoke-test": [
diff --git a/skills/ck/hooks/session-start.mjs b/skills/ck/hooks/session-start.mjs
index 0ef9cd2fa..47d3623b7 100644
--- a/skills/ck/hooks/session-start.mjs
+++ b/skills/ck/hooks/session-start.mjs
@@ -89,8 +89,11 @@ function main() {
 
   // Load skill (always inject — now only ~50 lines)
   // The host does not expand ${CLAUDE_SKILL_DIR} in hook output, so fill it in here.
+  // SKILL.md uses it inside double-quoted bash, so escape the characters bash
+  // still interprets there; the callback keeps `$&` etc. in the path literal.
+  const shellSkillDir = SKILL_DIR.replace(/[\\$`"]/g, '\\$&');
   const skill = existsSync(SKILL_FILE)
-    ? readFileSync(SKILL_FILE, 'utf8').replaceAll('${CLAUDE_SKILL_DIR}', SKILL_DIR)
+    ? readFileSync(SKILL_FILE, 'utf8').replaceAll('${CLAUDE_SKILL_DIR}', () => shellSkillDir)
     : '';
 
   const projects = readJson(PROJECTS_FILE) || {};
diff --git a/tests/skills/ck-paths.test.js b/tests/skills/ck-paths.test.js
index f9685e879..9ab5d88d4 100644
--- a/tests/skills/ck-paths.test.js
+++ b/tests/skills/ck-paths.test.js
@@ -78,7 +78,31 @@ async function runTests() {
       const { additionalContext } = JSON.parse(result.stdout);
       assert.ok(additionalContext.includes('# ck — Context Keeper'), 'SKILL.md was not injected');
       assert.ok(!additionalContext.includes('${CLAUDE_SKILL_DIR}'), 'skill dir placeholder left unexpanded');
-      assert.ok(additionalContext.includes(path.join(SKILL_DIR, 'commands')), 'skill dir not substituted');
+      // Escaped for double-quoted bash (Windows backslashes are doubled).
+      const shellCommandsDir = path.join(SKILL_DIR, 'commands').replace(/[\\$`"]/g, '\\$&');
+      assert.ok(additionalContext.includes(shellCommandsDir), 'skill dir not substituted');
+    } finally {
+      fs.rmSync(ctx.root, { recursive: true, force: true });
+    }
+  })) passed++; else failed++;
+
+  if (process.platform === 'win32') {
+    console.log('  - skipped shell-special skill dir test on Windows');
+  } else if (await test('hook-injected commands run from a skill dir with shell-special characters', async () => {
+    const ctx = tempEnv();
+    try {
+      const skillDir = path.join(ctx.root, 'skills $USER $& `x` "q"', 'ck');
+      fs.cpSync(SKILL_DIR, skillDir, { recursive: true });
+      const result = spawnSync(process.execPath, [path.join(skillDir, 'hooks', 'session-start.mjs')], {
+        cwd: ctx.project, env: ctx.env, input: '{}', encoding: 'utf8',
+      });
+      assert.strictEqual(result.status, 0, result.stderr);
+      const { additionalContext } = JSON.parse(result.stdout);
+      const listCommand = additionalContext.split('\n').find(line => line.includes('commands/list.mjs'));
+      assert.ok(listCommand, 'no list.mjs command injected');
+      const list = spawnSync('bash', ['-c', listCommand], { cwd: ctx.project, env: ctx.env, encoding: 'utf8' });
+      // No projects are registered, so list.mjs reaching its own message proves the path resolved.
+      assert.ok(list.stdout.includes('No projects registered'), `${listCommand}\n${list.stdout}${list.stderr}`);
     } finally {
       fs.rmSync(ctx.root, { recursive: true, force: true });
     }