fix: prepend YAML frontmatter to Cursor .mdc files (#1699)

* fix: prepend YAML frontmatter to Cursor .mdc files for auto-inclusion

Cursor IDE requires YAML frontmatter with `alwaysApply: true` in .mdc
rule files for them to be automatically loaded. Without this frontmatter,
users must manually configure glob patterns for the rules to take effect.

This fix adds frontmatter generation to both the bash and PowerShell
update-agent-context scripts, handling three scenarios:
- New .mdc file creation (frontmatter prepended after template processing)
- Existing .mdc file update without frontmatter (frontmatter added)
- Existing .mdc file with frontmatter (no duplication)

Closes #669

🤖 Generated with [Claude Code](https://claude.com/code)

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

* refactor: address Copilot review suggestions

- Handle CRLF line endings in frontmatter detection (grep '^---' instead
  of '^---$')
- Fix double blank line after frontmatter in PowerShell New-AgentFile
- Remove unused tempfile import from tests
- Add encoding="utf-8" to all open() calls for cross-platform safety

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

---------

Co-authored-by: Claude Opus 4.6 <noreply@anthropic.com>

.github/workflows/docs.yml

@@ -29,7 +29,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Checkout
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
         with:
           fetch-depth: 0 # Fetch all history for git info
 

.github/workflows/lint.yml

@@ -12,7 +12,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Checkout
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Run markdownlint-cli2
         uses: DavidAnson/markdownlint-cli2-action@v19

.github/workflows/release.yml

@@ -19,7 +19,7 @@ jobs:
       pull-requests: write
     steps:
       - name: Checkout repository
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
         with:
           fetch-depth: 0
           token: ${{ secrets.GITHUB_TOKEN }}

.github/workflows/test.yml

@@ -16,10 +16,10 @@ jobs:
         uses: actions/checkout@v4
 
       - name: Install uv
-        uses: astral-sh/setup-uv@v6
+        uses: astral-sh/setup-uv@v7
 
       - name: Set up Python
-        uses: actions/setup-python@v5
+        uses: actions/setup-python@v6
         with:
           python-version: "3.13"
 
@@ -36,10 +36,10 @@ jobs:
         uses: actions/checkout@v4
 
       - name: Install uv
-        uses: astral-sh/setup-uv@v6
+        uses: astral-sh/setup-uv@v7
 
       - name: Set up Python ${{ matrix.python-version }}
-        uses: actions/setup-python@v5
+        uses: actions/setup-python@v6
         with:
           python-version: ${{ matrix.python-version }}
 

extensions/EXTENSION-DEVELOPMENT-GUIDE.md

@@ -456,18 +456,20 @@ Users install with:
 specify extension add --from https://github.com/.../spec-kit-my-ext-1.0.0.zip
 ```
 
-### Option 3: Extension Catalog (Future)
+### Option 3: Community Reference Catalog
 
-Submit to official catalog:
+Submit to the community catalog for public discovery:
 
 1. **Fork** spec-kit repository
-2. **Add entry** to `extensions/catalog.json`
-3. **Create PR**
-4. **After merge**, users can install with:
+2. **Add entry** to `extensions/catalog.community.json`
+3. **Update** `extensions/README.md` with your extension
+4. **Create PR** following the [Extension Publishing Guide](EXTENSION-PUBLISHING-GUIDE.md)
+5. **After merge**, your extension becomes available:
+   - Users can browse `catalog.community.json` to discover your extension
+   - Users copy the entry to their own `catalog.json`
+   - Users install with: `specify extension add my-ext` (from their catalog)
 
-   ```bash
-   specify extension add my-ext  # No URL needed!
-   ```
+See the [Extension Publishing Guide](EXTENSION-PUBLISHING-GUIDE.md) for detailed submission instructions.
 
 ---
 

extensions/EXTENSION-PUBLISHING-GUIDE.md

@@ -129,26 +129,32 @@ specify extension add --from https://github.com/your-org/spec-kit-your-extension
 
 ## Submit to Catalog
 
+### Understanding the Catalogs
+
+Spec Kit uses a dual-catalog system. For details about how catalogs work, see the main [Extensions README](README.md#extension-catalogs).
+
+**For extension publishing**: All community extensions should be added to `catalog.community.json`. Users browse this catalog and copy extensions they trust into their own `catalog.json`.
+
 ### 1. Fork the spec-kit Repository
 
 ```bash
 # Fork on GitHub
-# https://github.com/statsperform/spec-kit/fork
+# https://github.com/github/spec-kit/fork
 
 # Clone your fork
 git clone https://github.com/YOUR-USERNAME/spec-kit.git
 cd spec-kit
 ```
 
-### 2. Add Extension to Catalog
+### 2. Add Extension to Community Catalog
 
-Edit `extensions/catalog.json` and add your extension:
+Edit `extensions/catalog.community.json` and add your extension:
 
 ```json
 {
   "schema_version": "1.0",
   "updated_at": "2026-01-28T15:54:00Z",
-  "catalog_url": "https://raw.githubusercontent.com/statsperform/spec-kit/main/extensions/catalog.json",
+  "catalog_url": "https://raw.githubusercontent.com/github/spec-kit/main/extensions/catalog.community.json",
   "extensions": {
     "your-extension": {
       "name": "Your Extension Name",
@@ -198,15 +204,25 @@ Edit `extensions/catalog.json` and add your extension:
 - Use current timestamp for `created_at` and `updated_at`
 - Update the top-level `updated_at` to current time
 
-### 3. Submit Pull Request
+### 3. Update Extensions README
+
+Add your extension to the Available Extensions table in `extensions/README.md`:
+
+```markdown
+| Your Extension Name | Brief description of what it does | [repo-name](https://github.com/your-org/spec-kit-your-extension) |
+```
+
+Insert your extension in alphabetical order in the table.
+
+### 4. Submit Pull Request
 
 ```bash
 # Create a branch
 git checkout -b add-your-extension
 
 # Commit your changes
-git add extensions/catalog.json
-git commit -m "Add your-extension to catalog
+git add extensions/catalog.community.json extensions/README.md
+git commit -m "Add your-extension to community catalog
 
 - Extension ID: your-extension
 - Version: 1.0.0
@@ -218,7 +234,7 @@ git commit -m "Add your-extension to catalog
 git push origin add-your-extension
 
 # Create Pull Request on GitHub
-# https://github.com/statsperform/spec-kit/compare
+# https://github.com/github/spec-kit/compare
 ```
 
 **Pull Request Template**:
@@ -243,6 +259,8 @@ Brief description of what your extension does.
 - [x] Extension tested on real project
 - [x] All commands working
 - [x] No security vulnerabilities
+- [x] Added to extensions/catalog.community.json
+- [x] Added to extensions/README.md Available Extensions table
 
 ### Testing
 Tested on:

extensions/EXTENSION-USER-GUIDE.md

@@ -76,13 +76,15 @@ vim .specify/extensions/jira/jira-config.yml
 
 ## Finding Extensions
 
+**Note**: By default, `specify extension search` uses your organization's catalog (`catalog.json`). If the catalog is empty, you won't see any results. See [Extension Catalogs](#extension-catalogs) to learn how to populate your catalog from the community reference catalog.
+
 ### Browse All Extensions
 
 ```bash
 specify extension search
 ```
 
-Shows all available extensions in the catalog.
+Shows all extensions in your organization's catalog.
 
 ### Search by Keyword
 
@@ -415,11 +417,15 @@ export SPECKIT_CATALOG_URL="https://example.com/staging/catalog.json"
 
 ---
 
+## Extension Catalogs
+
+For information about how Spec Kit's dual-catalog system works (`catalog.json` vs `catalog.community.json`), see the main [Extensions README](README.md#extension-catalogs).
+
 ## Organization Catalog Customization
 
-### Why the Default Catalog is Empty
+### Why Customize Your Catalog
 
-The default spec-kit catalog ships empty by design. This allows organizations to:
+Organizations customize their `catalog.json` to:
 
 - **Control available extensions** - Curate which extensions your team can install
 - **Host private extensions** - Internal tools that shouldn't be public

extensions/README.md

@@ -1,8 +1,74 @@
-# Spec Kit Community Extensions
+# Spec Kit Extensions
 
-Community-contributed extensions for [Spec Kit](https://github.com/github/spec-kit).
+Extension system for [Spec Kit](https://github.com/github/spec-kit) - add new functionality without bloating the core framework.
 
-## Available Extensions
+## Extension Catalogs
+
+Spec Kit provides two catalog files with different purposes:
+
+### Your Catalog (`catalog.json`)
+
+- **Purpose**: Default upstream catalog of extensions used by the Spec Kit CLI
+- **Default State**: Empty by design in the upstream project - you or your organization populate a fork/copy with extensions you trust
+- **Location (upstream)**: `extensions/catalog.json` in the GitHub-hosted spec-kit repo
+- **CLI Default**: The `specify extension` commands use the upstream catalog URL by default, unless overridden
+- **Org Catalog**: Point `SPECKIT_CATALOG_URL` at your organization's fork or hosted catalog JSON to use it instead of the upstream default
+- **Customization**: Copy entries from the community catalog into your org catalog, or add your own extensions directly
+
+**Example override:**
+```bash
+# Override the default upstream catalog with your organization's catalog
+export SPECKIT_CATALOG_URL="https://your-org.com/spec-kit/catalog.json"
+specify extension search  # Now uses your organization's catalog instead of the upstream default
+```
+
+### Community Reference Catalog (`catalog.community.json`)
+
+- **Purpose**: Browse available community-contributed extensions
+- **Status**: Active - contains extensions submitted by the community
+- **Location**: `extensions/catalog.community.json`
+- **Usage**: Reference catalog for discovering available extensions
+- **Submission**: Open to community contributions via Pull Request
+
+**How It Works:**
+
+## Making Extensions Available
+
+You control which extensions your team can discover and install:
+
+### Option 1: Curated Catalog (Recommended for Organizations)
+
+Populate your `catalog.json` with approved extensions:
+
+1. **Discover** extensions from various sources:
+   - Browse `catalog.community.json` for community extensions
+   - Find private/internal extensions in your organization's repos
+   - Discover extensions from trusted third parties
+2. **Review** extensions and choose which ones you want to make available
+3. **Add** those extension entries to your own `catalog.json`
+4. **Team members** can now discover and install them:
+   - `specify extension search` shows your curated catalog
+   - `specify extension add <name>` installs from your catalog
+
+**Benefits**: Full control over available extensions, team consistency, organizational approval workflow
+
+**Example**: Copy an entry from `catalog.community.json` to your `catalog.json`, then your team can discover and install it by name.
+
+### Option 2: Direct URLs (For Ad-hoc Use)
+
+Skip catalog curation - team members install directly using URLs:
+
+```bash
+specify extension add --from https://github.com/org/spec-kit-ext/archive/refs/tags/v1.0.0.zip
+```
+
+**Benefits**: Quick for one-off testing or private extensions
+
+**Tradeoff**: Extensions installed this way won't appear in `specify extension search` for other team members unless you also add them to your `catalog.json`.
+
+## Available Community Extensions
+
+The following community-contributed extensions are available in [`catalog.community.json`](catalog.community.json):
 
 | Extension | Purpose | URL |
 |-----------|---------|-----|
@@ -11,4 +77,43 @@ Community-contributed extensions for [Spec Kit](https://github.com/github/spec-k
 
 ## Adding Your Extension
 
-See the [Extension Publishing Guide](EXTENSION-PUBLISHING-GUIDE.md) for instructions on how to submit your extension to the community catalog.
+### Submission Process
+
+To add your extension to the community catalog:
+
+1. **Prepare your extension** following the [Extension Development Guide](EXTENSION-DEVELOPMENT-GUIDE.md)
+2. **Create a GitHub release** for your extension
+3. **Submit a Pull Request** that:
+   - Adds your extension to `extensions/catalog.community.json`
+   - Updates this README with your extension in the Available Extensions table
+4. **Wait for review** - maintainers will review and merge if criteria are met
+
+See the [Extension Publishing Guide](EXTENSION-PUBLISHING-GUIDE.md) for detailed step-by-step instructions.
+
+### Submission Checklist
+
+Before submitting, ensure:
+
+- ✅ Valid `extension.yml` manifest
+- ✅ Complete README with installation and usage instructions
+- ✅ LICENSE file included
+- ✅ GitHub release created with semantic version (e.g., v1.0.0)
+- ✅ Extension tested on a real project
+- ✅ All commands working as documented
+
+## Installing Extensions
+Once extensions are available (either in your catalog or via direct URL), install them:
+
+```bash
+# From your curated catalog (by name)
+specify extension search                  # See what's in your catalog
+specify extension add <extension-name>    # Install by name
+
+# Direct from URL (bypasses catalog)
+specify extension add --from https://github.com/<org>/<repo>/archive/refs/tags/<version>.zip
+
+# List installed extensions
+specify extension list
+```
+
+For more information, see the [Extension User Guide](EXTENSION-USER-GUIDE.md).

extensions/RFC-EXTENSION-SYSTEM.md

@@ -858,11 +858,41 @@ def should_execute_hook(hook: dict, config: dict) -> bool:
 
 ## Extension Discovery & Catalog
 
-### Central Catalog
+### Dual Catalog System
+
+Spec Kit uses two catalog files with different purposes:
+
+#### User Catalog (`catalog.json`)
 
 **URL**: `https://raw.githubusercontent.com/github/spec-kit/main/extensions/catalog.json`
 
-**Format**:
+- **Purpose**: Organization's curated catalog of approved extensions
+- **Default State**: Empty by design - users populate with extensions they trust
+- **Usage**: Default catalog used by `specify extension` CLI commands
+- **Control**: Organizations maintain their own fork/version for their teams
+
+#### Community Reference Catalog (`catalog.community.json`)
+
+**URL**: `https://raw.githubusercontent.com/github/spec-kit/main/extensions/catalog.community.json`
+
+- **Purpose**: Reference catalog of available community-contributed extensions
+- **Verification**: Community extensions may have `verified: false` initially
+- **Status**: Active - open for community contributions
+- **Submission**: Via Pull Request following the Extension Publishing Guide
+- **Usage**: Browse to discover extensions, then copy to your `catalog.json`
+
+**How It Works:**
+
+1. **Discover**: Browse `catalog.community.json` to find available extensions
+2. **Review**: Evaluate extensions for security, quality, and organizational fit
+3. **Curate**: Copy approved extension entries from community catalog to your `catalog.json`
+4. **Install**: Use `specify extension add <name>` (pulls from your curated catalog)
+
+This approach gives organizations full control over which extensions are available to their teams while maintaining a shared community resource for discovery.
+
+### Catalog Format
+
+**Format** (same for both catalogs):
 
 ```json
 {
@@ -931,25 +961,52 @@ specify extension info jira
 
 ### Custom Catalogs
 
-Organizations can host private catalogs:
+**⚠️ FUTURE FEATURE - NOT YET IMPLEMENTED**
+
+The following catalog management commands are proposed design concepts but are not yet available in the current implementation:
 
 ```bash
-# Add custom catalog
+# Add custom catalog (FUTURE - NOT AVAILABLE)
 specify extension add-catalog https://internal.company.com/spec-kit/catalog.json
 
-# Set as default
+# Set as default (FUTURE - NOT AVAILABLE)
 specify extension set-catalog --default https://internal.company.com/spec-kit/catalog.json
 
-# List catalogs
+# List catalogs (FUTURE - NOT AVAILABLE)
 specify extension catalogs
 ```
 
-**Catalog priority**:
+**Proposed catalog priority** (future design):
 
-1. Project-specific catalog (`.specify/extension-catalogs.yml`)
-2. User-level catalog (`~/.specify/extension-catalogs.yml`)
+1. Project-specific catalog (`.specify/extension-catalogs.yml`) - *not implemented*
+2. User-level catalog (`~/.specify/extension-catalogs.yml`) - *not implemented*
 3. Default GitHub catalog
 
+#### Current Implementation: SPECKIT_CATALOG_URL
+
+**The currently available method** for using custom catalogs is the `SPECKIT_CATALOG_URL` environment variable:
+
+```bash
+# Point to your organization's catalog
+export SPECKIT_CATALOG_URL="https://internal.company.com/spec-kit/catalog.json"
+
+# All extension commands now use your custom catalog
+specify extension search       # Uses custom catalog
+specify extension add jira     # Installs from custom catalog
+```
+
+**Requirements:**
+- URL must use HTTPS (HTTP only allowed for localhost testing)
+- Catalog must follow the standard catalog.json schema
+- Must be publicly accessible or accessible within your network
+
+**Example for testing:**
+```bash
+# Test with localhost during development
+export SPECKIT_CATALOG_URL="http://localhost:8000/catalog.json"
+specify extension search
+```
+
 ---
 
 ## CLI Commands

scripts/bash/update-agent-context.sh

@@ -351,10 +351,19 @@ create_new_agent_file() {
     # Convert \n sequences to actual newlines
     newline=$(printf '\n')
     sed -i.bak2 "s/\\\\n/${newline}/g" "$temp_file"
-    
+
     # Clean up backup files
     rm -f "$temp_file.bak" "$temp_file.bak2"
-    
+
+    # Prepend Cursor frontmatter for .mdc files so rules are auto-included
+    if [[ "$target_file" == *.mdc ]]; then
+        local frontmatter_file
+        frontmatter_file=$(mktemp) || return 1
+        printf '%s\n' "---" "description: Project Development Guidelines" "globs: [\"**/*\"]" "alwaysApply: true" "---" "" > "$frontmatter_file"
+        cat "$temp_file" >> "$frontmatter_file"
+        mv "$frontmatter_file" "$temp_file"
+    fi
+
     return 0
 }
 
@@ -492,13 +501,24 @@ update_existing_agent_file() {
         changes_entries_added=true
     fi
     
+    # Ensure Cursor .mdc files have YAML frontmatter for auto-inclusion
+    if [[ "$target_file" == *.mdc ]]; then
+        if ! head -1 "$temp_file" | grep -q '^---'; then
+            local frontmatter_file
+            frontmatter_file=$(mktemp) || { rm -f "$temp_file"; return 1; }
+            printf '%s\n' "---" "description: Project Development Guidelines" "globs: [\"**/*\"]" "alwaysApply: true" "---" "" > "$frontmatter_file"
+            cat "$temp_file" >> "$frontmatter_file"
+            mv "$frontmatter_file" "$temp_file"
+        fi
+    fi
+
     # Move temp file to target atomically
     if ! mv "$temp_file" "$target_file"; then
         log_error "Failed to update target file"
         rm -f "$temp_file"
         return 1
     fi
-    
+
     return 0
 }
 #==============================================================================

scripts/powershell/update-agent-context.ps1

@@ -258,6 +258,12 @@ function New-AgentFile {
     # Convert literal \n sequences introduced by Escape to real newlines
     $content = $content -replace '\\n',[Environment]::NewLine
 
+    # Prepend Cursor frontmatter for .mdc files so rules are auto-included
+    if ($TargetFile -match '\.mdc$') {
+        $frontmatter = @('---','description: Project Development Guidelines','globs: ["**/*"]','alwaysApply: true','---','') -join [Environment]::NewLine
+        $content = $frontmatter + $content
+    }
+
     $parent = Split-Path -Parent $TargetFile
     if (-not (Test-Path $parent)) { New-Item -ItemType Directory -Path $parent | Out-Null }
     Set-Content -LiteralPath $TargetFile -Value $content -NoNewline -Encoding utf8
@@ -334,6 +340,12 @@ function Update-ExistingAgentFile {
         $newTechEntries | ForEach-Object { $output.Add($_) }
     }
 
+    # Ensure Cursor .mdc files have YAML frontmatter for auto-inclusion
+    if ($TargetFile -match '\.mdc$' -and $output.Count -gt 0 -and $output[0] -ne '---') {
+        $frontmatter = @('---','description: Project Development Guidelines','globs: ["**/*"]','alwaysApply: true','---','')
+        $output.InsertRange(0, $frontmatter)
+    }
+
     Set-Content -LiteralPath $TargetFile -Value ($output -join [Environment]::NewLine) -Encoding utf8
     return $true
 }

tests/test_cursor_frontmatter.py

@@ -0,0 +1,263 @@
+"""
+Tests for Cursor .mdc frontmatter generation (issue #669).
+
+Verifies that update-agent-context.sh properly prepends YAML frontmatter
+to .mdc files so that Cursor IDE auto-includes the rules.
+"""
+
+import os
+import shutil
+import subprocess
+import textwrap
+
+import pytest
+
+SCRIPT_PATH = os.path.join(
+    os.path.dirname(__file__),
+    os.pardir,
+    "scripts",
+    "bash",
+    "update-agent-context.sh",
+)
+
+EXPECTED_FRONTMATTER_LINES = [
+    "---",
+    "description: Project Development Guidelines",
+    'globs: ["**/*"]',
+    "alwaysApply: true",
+    "---",
+]
+
+requires_git = pytest.mark.skipif(
+    shutil.which("git") is None,
+    reason="git is not installed",
+)
+
+
+class TestScriptFrontmatterPattern:
+    """Static analysis — no git required."""
+
+    def test_create_new_has_mdc_frontmatter_logic(self):
+        """create_new_agent_file() must contain .mdc frontmatter logic."""
+        with open(SCRIPT_PATH, encoding="utf-8") as f:
+            content = f.read()
+        assert 'if [[ "$target_file" == *.mdc ]]' in content
+        assert "alwaysApply: true" in content
+
+    def test_update_existing_has_mdc_frontmatter_logic(self):
+        """update_existing_agent_file() must also handle .mdc frontmatter."""
+        with open(SCRIPT_PATH, encoding="utf-8") as f:
+            content = f.read()
+        # There should be two occurrences of the .mdc check — one per function
+        occurrences = content.count('if [[ "$target_file" == *.mdc ]]')
+        assert occurrences >= 2, (
+            f"Expected at least 2 .mdc frontmatter checks, found {occurrences}"
+        )
+
+    def test_powershell_script_has_mdc_frontmatter_logic(self):
+        """PowerShell script must also handle .mdc frontmatter."""
+        ps_path = os.path.join(
+            os.path.dirname(__file__),
+            os.pardir,
+            "scripts",
+            "powershell",
+            "update-agent-context.ps1",
+        )
+        with open(ps_path, encoding="utf-8") as f:
+            content = f.read()
+        assert "alwaysApply: true" in content
+        occurrences = content.count(r"\.mdc$")
+        assert occurrences >= 2, (
+            f"Expected at least 2 .mdc frontmatter checks in PS script, found {occurrences}"
+        )
+
+
+@requires_git
+class TestCursorFrontmatterIntegration:
+    """Integration tests using a real git repo."""
+
+    @pytest.fixture
+    def git_repo(self, tmp_path):
+        """Create a minimal git repo with the spec-kit structure."""
+        repo = tmp_path / "repo"
+        repo.mkdir()
+
+        # Init git repo
+        subprocess.run(
+            ["git", "init"], cwd=str(repo), capture_output=True, check=True
+        )
+        subprocess.run(
+            ["git", "config", "user.email", "test@test.com"],
+            cwd=str(repo),
+            capture_output=True,
+            check=True,
+        )
+        subprocess.run(
+            ["git", "config", "user.name", "Test"],
+            cwd=str(repo),
+            capture_output=True,
+            check=True,
+        )
+
+        # Create .specify dir with config
+        specify_dir = repo / ".specify"
+        specify_dir.mkdir()
+        (specify_dir / "config.yaml").write_text(
+            textwrap.dedent("""\
+                project_type: webapp
+                language: python
+                framework: fastapi
+                database: N/A
+            """)
+        )
+
+        # Create template
+        templates_dir = specify_dir / "templates"
+        templates_dir.mkdir()
+        (templates_dir / "agent-file-template.md").write_text(
+            "# [PROJECT NAME] Development Guidelines\n\n"
+            "Auto-generated from all feature plans. Last updated: [DATE]\n\n"
+            "## Active Technologies\n\n"
+            "[EXTRACTED FROM ALL PLAN.MD FILES]\n\n"
+            "## Project Structure\n\n"
+            "[ACTUAL STRUCTURE FROM PLANS]\n\n"
+            "## Development Commands\n\n"
+            "[ONLY COMMANDS FOR ACTIVE TECHNOLOGIES]\n\n"
+            "## Coding Conventions\n\n"
+            "[LANGUAGE-SPECIFIC, ONLY FOR LANGUAGES IN USE]\n\n"
+            "## Recent Changes\n\n"
+            "[LAST 3 FEATURES AND WHAT THEY ADDED]\n"
+        )
+
+        # Create initial commit
+        subprocess.run(
+            ["git", "add", "-A"], cwd=str(repo), capture_output=True, check=True
+        )
+        subprocess.run(
+            ["git", "commit", "-m", "init"],
+            cwd=str(repo),
+            capture_output=True,
+            check=True,
+        )
+
+        # Create a feature branch so CURRENT_BRANCH detection works
+        subprocess.run(
+            ["git", "checkout", "-b", "001-test-feature"],
+            cwd=str(repo),
+            capture_output=True,
+            check=True,
+        )
+
+        # Create a spec so the script detects the feature
+        spec_dir = repo / "specs" / "001-test-feature"
+        spec_dir.mkdir(parents=True)
+        (spec_dir / "plan.md").write_text(
+            "# Test Feature Plan\n\n"
+            "## Technology Stack\n\n"
+            "- Language: Python\n"
+            "- Framework: FastAPI\n"
+        )
+
+        return repo
+
+    def _run_update(self, repo, agent_type="cursor-agent"):
+        """Run update-agent-context.sh for a specific agent type."""
+        script = os.path.abspath(SCRIPT_PATH)
+        result = subprocess.run(
+            ["bash", script, agent_type],
+            cwd=str(repo),
+            capture_output=True,
+            text=True,
+            timeout=30,
+        )
+        return result
+
+    def test_new_mdc_file_has_frontmatter(self, git_repo):
+        """Creating a new .mdc file must include YAML frontmatter."""
+        result = self._run_update(git_repo)
+        assert result.returncode == 0, f"Script failed: {result.stderr}"
+
+        mdc_file = git_repo / ".cursor" / "rules" / "specify-rules.mdc"
+        assert mdc_file.exists(), "Cursor .mdc file was not created"
+
+        content = mdc_file.read_text()
+        lines = content.splitlines()
+
+        # First line must be the opening ---
+        assert lines[0] == "---", f"Expected frontmatter start, got: {lines[0]}"
+
+        # Check all frontmatter lines are present
+        for expected in EXPECTED_FRONTMATTER_LINES:
+            assert expected in content, f"Missing frontmatter line: {expected}"
+
+        # Content after frontmatter should be the template content
+        assert "Development Guidelines" in content
+
+    def test_existing_mdc_without_frontmatter_gets_it_added(self, git_repo):
+        """Updating an existing .mdc file that lacks frontmatter must add it."""
+        # First, create the file WITHOUT frontmatter (simulating pre-fix state)
+        cursor_dir = git_repo / ".cursor" / "rules"
+        cursor_dir.mkdir(parents=True, exist_ok=True)
+        mdc_file = cursor_dir / "specify-rules.mdc"
+        mdc_file.write_text(
+            "# repo Development Guidelines\n\n"
+            "Auto-generated from all feature plans. Last updated: 2025-01-01\n\n"
+            "## Active Technologies\n\n"
+            "- Python + FastAPI (main)\n\n"
+            "## Recent Changes\n\n"
+            "- main: Added Python + FastAPI\n"
+        )
+
+        result = self._run_update(git_repo)
+        assert result.returncode == 0, f"Script failed: {result.stderr}"
+
+        content = mdc_file.read_text()
+        lines = content.splitlines()
+
+        assert lines[0] == "---", f"Expected frontmatter start, got: {lines[0]}"
+        for expected in EXPECTED_FRONTMATTER_LINES:
+            assert expected in content, f"Missing frontmatter line: {expected}"
+
+    def test_existing_mdc_with_frontmatter_not_duplicated(self, git_repo):
+        """Updating an .mdc file that already has frontmatter must not duplicate it."""
+        cursor_dir = git_repo / ".cursor" / "rules"
+        cursor_dir.mkdir(parents=True, exist_ok=True)
+        mdc_file = cursor_dir / "specify-rules.mdc"
+
+        frontmatter = (
+            "---\n"
+            "description: Project Development Guidelines\n"
+            'globs: ["**/*"]\n'
+            "alwaysApply: true\n"
+            "---\n\n"
+        )
+        body = (
+            "# repo Development Guidelines\n\n"
+            "Auto-generated from all feature plans. Last updated: 2025-01-01\n\n"
+            "## Active Technologies\n\n"
+            "- Python + FastAPI (main)\n\n"
+            "## Recent Changes\n\n"
+            "- main: Added Python + FastAPI\n"
+        )
+        mdc_file.write_text(frontmatter + body)
+
+        result = self._run_update(git_repo)
+        assert result.returncode == 0, f"Script failed: {result.stderr}"
+
+        content = mdc_file.read_text()
+        # Count occurrences of the frontmatter delimiter
+        assert content.count("alwaysApply: true") == 1, (
+            "Frontmatter was duplicated"
+        )
+
+    def test_non_mdc_file_has_no_frontmatter(self, git_repo):
+        """Non-.mdc agent files (e.g., Claude) must NOT get frontmatter."""
+        result = self._run_update(git_repo, agent_type="claude")
+        assert result.returncode == 0, f"Script failed: {result.stderr}"
+
+        claude_file = git_repo / ".claude" / "CLAUDE.md"
+        if claude_file.exists():
+            content = claude_file.read_text()
+            assert not content.startswith("---"), (
+                "Non-mdc file should not have frontmatter"
+            )