feat(extensions): add --force flag to extension add for overwrite reinstall

src/specify_cli/__init__.py

@@ -4262,6 +4262,7 @@ def extension_add(
     extension: str = typer.Argument(help="Extension name or path"),
     dev: bool = typer.Option(False, "--dev", help="Install from local directory"),
     from_url: Optional[str] = typer.Option(None, "--from", help="Install from custom URL"),
+    force: bool = typer.Option(False, "--force", help="Overwrite if already installed"),
     priority: int = typer.Option(10, "--priority", help="Resolution priority (lower = higher precedence, default 10)"),
 ):
     """Install an extension."""
@@ -4276,6 +4277,9 @@ def extension_add(
     manager = ExtensionManager(project_root)
     speckit_version = get_speckit_version()
 
+    if force:
+        console.print("[yellow]--force:[/yellow] Will overwrite if already installed\n")
+
     try:
         with console.status(f"[cyan]Installing extension: {extension}[/cyan]"):
             if dev:
@@ -4289,7 +4293,12 @@ def extension_add(
                     console.print(f"[red]Error:[/red] No extension.yml found in {source_path}")
                     raise typer.Exit(1)
 
-                manifest = manager.install_from_directory(source_path, speckit_version, priority=priority)
+                if force:
+                    console.print(f"[yellow]--force:[/yellow] Reinstalling from [cyan]{source_path}[/cyan]...")
+
+                manifest = manager.install_from_directory(
+                    source_path, speckit_version, priority=priority, force=force
+                )
 
             elif from_url:
                 # Install from URL (ZIP file)
@@ -4324,7 +4333,7 @@ def extension_add(
                     zip_path.write_bytes(zip_data)
 
                     # Install from downloaded ZIP
-                    manifest = manager.install_from_zip(zip_path, speckit_version, priority=priority)
+                    manifest = manager.install_from_zip(zip_path, speckit_version, priority=priority, force=force)
                 except urllib.error.URLError as e:
                     console.print(f"[red]Error:[/red] Failed to download from {from_url}: {e}")
                     raise typer.Exit(1)
@@ -4337,7 +4346,9 @@ def extension_add(
                 # Try bundled extensions first (shipped with spec-kit)
                 bundled_path = _locate_bundled_extension(extension)
                 if bundled_path is not None:
-                    manifest = manager.install_from_directory(bundled_path, speckit_version, priority=priority)
+                    manifest = manager.install_from_directory(
+                        bundled_path, speckit_version, priority=priority, force=force
+                    )
                 else:
                     # Install from catalog (also resolves display names to IDs)
                     catalog = ExtensionCatalog(project_root)
@@ -4358,7 +4369,9 @@ def extension_add(
                     if resolved_id != extension:
                         bundled_path = _locate_bundled_extension(resolved_id)
                         if bundled_path is not None:
-                            manifest = manager.install_from_directory(bundled_path, speckit_version, priority=priority)
+                            manifest = manager.install_from_directory(
+                                bundled_path, speckit_version, priority=priority, force=force
+                            )
 
                     if bundled_path is None:
                         # Bundled extensions without a download URL must come from the local package
@@ -4394,7 +4407,7 @@ def extension_add(
 
                         try:
                             # Install from downloaded ZIP
-                            manifest = manager.install_from_zip(zip_path, speckit_version, priority=priority)
+                            manifest = manager.install_from_zip(zip_path, speckit_version, priority=priority, force=force)
                         finally:
                             # Clean up downloaded ZIP
                             if zip_path.exists():

src/specify_cli/extensions.py

@@ -1132,6 +1132,7 @@ def install_from_directory(
         speckit_version: str,
         register_commands: bool = True,
         priority: int = 10,
+        force: bool = False,
     ) -> ExtensionManifest:
         """Install extension from a local directory.
 
@@ -1140,6 +1141,8 @@ def install_from_directory(
             speckit_version: Current spec-kit version
             register_commands: If True, register commands with AI agents
             priority: Resolution priority (lower = higher precedence, default 10)
+            force: If True and extension is already installed, remove it first
+                   before proceeding with installation
 
         Returns:
             Installed extension manifest
@@ -1161,14 +1164,22 @@ def install_from_directory(
 
         # Check if already installed
         if self.registry.is_installed(manifest.id):
-            raise ExtensionError(
-                f"Extension '{manifest.id}' is already installed. "
-                f"Use 'specify extension remove {manifest.id}' first."
-            )
+            if not force:
+                raise ExtensionError(
+                    f"Extension '{manifest.id}' is already installed. "
+                    f"Use 'specify extension remove {manifest.id}' first, "
+                    f"or retry with --force to overwrite."
+                )
 
         # Reject manifests that would shadow core commands or installed extensions.
         self._validate_install_conflicts(manifest)
 
+        # Remove existing installation AFTER all validations pass so that a
+        # validation failure doesn't leave the user with a half-uninstalled
+        # extension (configs stranded in .backup/).
+        if force and self.registry.is_installed(manifest.id):
+            self.remove(manifest.id)
+
         # Install extension
         dest_dir = self.extensions_dir / manifest.id
         if dest_dir.exists():
@@ -1194,6 +1205,15 @@ def install_from_directory(
         hook_executor = HookExecutor(self.project_root)
         hook_executor.register_hooks(manifest)
 
+        # Restore config files from backup when reinstalling with --force
+        if force:
+            backup_config_dir = self.extensions_dir / ".backup" / manifest.id
+            if backup_config_dir.exists():
+                for cfg_file in backup_config_dir.iterdir():
+                    if cfg_file.is_file():
+                        shutil.copy2(cfg_file, dest_dir / cfg_file.name)
+                shutil.rmtree(backup_config_dir)
+
         # Update registry
         self.registry.add(manifest.id, {
             "version": manifest.version,
@@ -1212,13 +1232,16 @@ def install_from_zip(
         zip_path: Path,
         speckit_version: str,
         priority: int = 10,
+        force: bool = False,
     ) -> ExtensionManifest:
         """Install extension from ZIP file.
 
         Args:
             zip_path: Path to extension ZIP file
             speckit_version: Current spec-kit version
             priority: Resolution priority (lower = higher precedence, default 10)
+            force: If True and extension is already installed, remove it first
+                   before proceeding with installation
 
         Returns:
             Installed extension manifest
@@ -1265,7 +1288,9 @@ def install_from_zip(
                 raise ValidationError("No extension.yml found in ZIP file")
 
             # Install from extracted directory
-            return self.install_from_directory(extension_dir, speckit_version, priority=priority)
+            return self.install_from_directory(
+                extension_dir, speckit_version, priority=priority, force=force
+            )
 
     def remove(self, extension_id: str, keep_config: bool = False) -> bool:
         """Remove an installed extension.

tests/test_extensions.py

@@ -780,6 +780,102 @@ def test_install_duplicate(self, extension_dir, project_dir):
         with pytest.raises(ExtensionError, match="already installed"):
             manager.install_from_directory(extension_dir, "0.1.0", register_commands=False)
 
+    def test_install_force_reinstall(self, extension_dir, project_dir):
+        """Test force-reinstalling an already-installed extension."""
+        manager = ExtensionManager(project_dir)
+
+        # Install once
+        manifest1 = manager.install_from_directory(
+            extension_dir, "0.1.0", register_commands=False
+        )
+        assert manager.registry.is_installed("test-ext")
+
+        # Force-reinstall
+        manifest2 = manager.install_from_directory(
+            extension_dir, "0.1.0", register_commands=False, force=True
+        )
+
+        assert manifest2.id == "test-ext"
+        assert manager.registry.is_installed("test-ext")
+        # Check extension directory was recreated
+        ext_dir = project_dir / ".specify" / "extensions" / "test-ext"
+        assert ext_dir.exists()
+        assert (ext_dir / "extension.yml").exists()
+        assert (ext_dir / "commands" / "hello.md").exists()
+
+    def test_install_force_config_preserved(self, extension_dir, project_dir):
+        """Test that config files are preserved when force-reinstalling."""
+        manager = ExtensionManager(project_dir)
+
+        # Install once
+        manager.install_from_directory(
+            extension_dir, "0.1.0", register_commands=False
+        )
+
+        # Create a config file in the installed extension directory
+        ext_dir = project_dir / ".specify" / "extensions" / "test-ext"
+        config_file = ext_dir / "test-ext-config.yml"
+        config_file.write_text("test: config")
+
+        # Force-reinstall
+        manager.install_from_directory(
+            extension_dir, "0.1.0", register_commands=False, force=True
+        )
+
+        # Config file should still exist after reinstall
+        new_config = ext_dir / "test-ext-config.yml"
+        assert new_config.exists()
+        assert new_config.read_text() == "test: config"
+
+    def test_install_force_without_existing(self, extension_dir, project_dir):
+        """Test force-install when extension is NOT already installed (works normally)."""
+        manager = ExtensionManager(project_dir)
+
+        manifest = manager.install_from_directory(
+            extension_dir, "0.1.0", register_commands=False, force=True
+        )
+
+        assert manifest.id == "test-ext"
+        assert manager.registry.is_installed("test-ext")
+
+    def test_install_zip_force_reinstall(self, extension_dir, project_dir):
+        """Test force-reinstalling from ZIP when already installed."""
+        import zipfile
+        import tempfile
+
+        manager = ExtensionManager(project_dir)
+
+        # Install once from directory
+        manager.install_from_directory(extension_dir, "0.1.0", register_commands=False)
+
+        # Create a ZIP of the extension in a temp directory (not NamedTemporaryFile,
+        # which can fail on Windows due to file locking).
+        with tempfile.TemporaryDirectory() as tmpdir:
+            zip_path = Path(tmpdir) / "test-ext.zip"
+            with zipfile.ZipFile(zip_path, "w") as zf:
+                for f in extension_dir.rglob("*"):
+                    if f.is_file():
+                        zf.write(f, f.relative_to(extension_dir))
+
+            # Force-reinstall from ZIP
+            manifest = manager.install_from_zip(
+                zip_path, "0.1.0", force=True
+            )
+
+        assert manifest.id == "test-ext"
+        assert manager.registry.is_installed("test-ext")
+        ext_dir = project_dir / ".specify" / "extensions" / "test-ext"
+        assert ext_dir.exists()
+
+    def test_install_duplicate_error_mentions_force(self, extension_dir, project_dir):
+        """Test that duplicate install error message suggests --force."""
+        manager = ExtensionManager(project_dir)
+
+        manager.install_from_directory(extension_dir, "0.1.0", register_commands=False)
+
+        with pytest.raises(ExtensionError, match="--force"):
+            manager.install_from_directory(extension_dir, "0.1.0", register_commands=False)
+
     def test_install_rejects_extension_id_in_core_namespace(self, temp_dir, project_dir):
         """Install should reject extension IDs that shadow core commands."""
         import yaml
@@ -4321,3 +4417,69 @@ def test_remove_confirmation_plural_commands(self, tmp_path, extension_dir):
             )
 
         assert "2 commands" in result.output
+
+
+class TestExtensionForceCLI:
+    """CLI tests for `specify extension add --dev --force`."""
+
+    def _create_minimal_extension(self, base_dir: str | Path, ext_id: str = "test-ext") -> Path:
+        """Create a minimal extension directory with manifest."""
+        import yaml
+
+        ext_dir = Path(base_dir) / ext_id
+        ext_dir.mkdir(parents=True, exist_ok=True)
+        (ext_dir / "commands").mkdir()
+
+        manifest = {
+            "schema_version": "1.0",
+            "extension": {
+                "id": ext_id,
+                "name": "Test Extension",
+                "version": "1.0.0",
+                "description": "Test",
+            },
+            "requires": {"speckit_version": ">=0.1.0"},
+            "provides": {
+                "commands": [
+                    {
+                        "name": f"speckit.{ext_id}.hello",
+                        "file": "commands/hello.md",
+                        "description": "Test command",
+                    }
+                ]
+            },
+        }
+
+        (ext_dir / "extension.yml").write_text(yaml.dump(manifest))
+        (ext_dir / "commands" / "hello.md").write_text(
+            "---\ndescription: Test\n---\n\nHello $ARGUMENTS\n"
+        )
+        return ext_dir
+
+    def test_add_dev_force_reinstall(self, tmp_path):
+        """extension add --dev --force should reinstall without error."""
+        from typer.testing import CliRunner
+        from unittest.mock import patch
+        from specify_cli import app
+
+        project_dir = tmp_path / "project"
+        project_dir.mkdir()
+        (project_dir / ".specify").mkdir()
+
+        ext_src = self._create_minimal_extension(tmp_path)
+
+        runner = CliRunner()
+        with patch.object(Path, "cwd", return_value=project_dir):
+            # First install
+            result1 = runner.invoke(
+                app, ["extension", "add", str(ext_src), "--dev"], catch_exceptions=False
+            )
+            assert result1.exit_code == 0, strip_ansi(result1.output)
+            assert "installed" in strip_ansi(result1.output)
+
+            # Force reinstall
+            result2 = runner.invoke(
+                app, ["extension", "add", str(ext_src), "--dev", "--force"], catch_exceptions=False
+            )
+            assert result2.exit_code == 0, strip_ansi(result2.output)
+            assert "installed" in strip_ansi(result2.output)