fix: auto-override existing team-ai-directives on reinstall

Author: kanfil

.gitignore

@@ -51,6 +51,10 @@ bin/
 sdd-*/
 docs/dev
 
+# Synced copies (local working copies, not committed)
+.specify/
+.opencode/
+
 # User-specific configuration (now stored globally in ~/.config/specify/)
 # Old local config directory is kept for backward compatibility but should not be used
 .specify/config/

CHANGELOG.md

@@ -4,6 +4,13 @@ All notable changes to the Specify CLI and templates are documented here.
 
 # [Unreleased]
 
+### Fixed
+
+- **team-ai-directives override**: `sync_team_ai_directives()` now auto-overrides existing installation
+  - Added `force` parameter to allow reinstalling over existing team-ai-directives
+  - Matches pre-installed extension behavior (unconditionally overwrites)
+  - Removes need to manually run `specify extension remove team-ai-directives` first
+
 # [0.5.15] - 2026-04-23
 
 ### Changed

pyproject.toml

@@ -1,6 +1,6 @@
 [project]
 name = "agentic-sdlc-specify-cli"
-version = "0.5.15"
+version = "0.5.16"
 description = "Specify CLI (tikalk fork). Agentic SDLC toolkit for Spec-Driven Development with pre-installed extensions and AI integrations."
 requires-python = ">=3.11"
 dependencies = [

src/specify_cli/__init__.py

@@ -222,7 +222,7 @@ def _derive_target_repo_from_url(zip_url: str) -> str:
 
 
 def sync_team_ai_directives(
-    repo_url: str, project_root: Path, *, install: bool = True, skip_tls: bool = False
+    repo_url: str, project_root: Path, *, install: bool = True, force: bool = False
 ) -> tuple[str, Path]:
     """Install team-ai-directives as extension from ZIP URL or local path.
 
@@ -231,7 +231,8 @@ def sync_team_ai_directives(
         project_root: Project root directory
         install: If True, copy local directories to .specify/extensions/.
                  If False, use local directories in-place (reference mode).
-        skip_tls: Skip TLS verification (for HTTPS URLs)
+        force: If True, remove existing team-ai-directives before reinstalling.
+              If False (default), raise error if already installed.
 
     Returns:
         Tuple of (status, path) where status is "installed", "local", or "reference"
@@ -266,6 +267,11 @@ def sync_team_ai_directives(
         # Install mode: copy to .specify/extensions/
         ext_manager = ExtensionManager(project_root)
         speckit_version = get_speckit_version()
+
+        # Force override: remove existing team-ai-directives before reinstalling
+        if force and ext_manager.registry.is_installed(TEAM_DIRECTIVES_DIRNAME):
+            ext_manager.remove(TEAM_DIRECTIVES_DIRNAME)
+
         manifest = ext_manager.install_from_directory(
             potential_path, speckit_version, priority=1
         )
@@ -279,6 +285,10 @@ def sync_team_ai_directives(
         ext_manager = ExtensionManager(project_root)
         speckit_version = get_speckit_version()
 
+        # Force override: remove existing team-ai-directives before reinstalling
+        if force and ext_manager.registry.is_installed(TEAM_DIRECTIVES_DIRNAME):
+            ext_manager.remove(TEAM_DIRECTIVES_DIRNAME)
+
         download_dir = project_root / ".specify" / "extensions" / ".cache" / "downloads"
         download_dir.mkdir(parents=True, exist_ok=True)
         zip_path = download_dir / "team-ai-directives-download.zip"

src/specify_cli/cli_customization.py

@@ -337,9 +337,9 @@ def pre_init(
             )
             tracker.complete("team-directives", f"referenced: {directives_path}")
         else:
-            # ZIP URL: install to .specify/extensions/
+            # ZIP URL: install to .specify/extensions/ (auto-override existing)
             status, directives_path = sync_team_ai_directives(
-                team_ai_directives, project_path, install=True
+                team_ai_directives, project_path, install=True, force=True
             )
             if status == "installed":
                 tracker.complete("team-directives", f"installed to {directives_path}")