fix: preserve .vscode/settings.json and script +x bit on integration upgrade (#3020)

* fix: preserve .vscode/settings.json and script +x bit on integration upgrade

During 'specify integration upgrade', Phase 2 stale-cleanup removes files
present in the old manifest but absent from the new one. Copilot's setup()
merges into an existing .vscode/settings.json and stops tracking it, so the
file was being deleted on upgrade (destroying user settings). Add a
stale_cleanup_exclusions() hook that integrations use to protect such
conditionally-tracked merge targets. Also restore the executable bit on
shared .sh scripts after the managed-refresh step on POSIX.

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* fix: address review on stale-cleanup fix

- Normalize stale_cleanup_exclusions() to POSIX before subtracting from
  manifest keys, so exclusions built with os.path.join / backslashes still
  match on Windows.
- Strengthen test_upgrade_preserves_existing_vscode_settings to add a
  user-defined key and assert it survives the upgrade (via --force, exercising
  the merge + stale-cleanup path) instead of the brittle after == before check.

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

---------

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

src/specify_cli/integrations/_migrate_commands.py

@@ -2,6 +2,7 @@
 from __future__ import annotations
 
 import os
+from pathlib import PurePath
 
 import typer
 
@@ -461,6 +462,9 @@ def integration_upgrade(
                 raise _SharedTemplateRefreshError(
                     f"Failed to refresh shared infrastructure for '{key}': {exc}"
                 ) from exc
+            if os.name != "nt":
+                from .. import ensure_executable_scripts
+                ensure_executable_scripts(project_root)
         new_manifest.save()
         _write_integration_json(project_root, installed_key, installed_keys, settings)
         if installed_key == key:
@@ -478,7 +482,13 @@ def integration_upgrade(
     # Phase 2: Remove stale files from old manifest that are not in the new one
     old_files = old_manifest.files
     new_files = new_manifest.files
-    stale_keys = set(old_files) - set(new_files)
+    # Exclude integration-declared paths that use conditional manifest tracking
+    # (e.g. merge targets like .vscode/settings.json) so they are never deleted
+    # as "stale" while still being actively managed.  Manifest keys are stored
+    # in POSIX form, so normalize the exclusions the same way before subtracting
+    # (an integration may build paths with os.path.join / backslashes).
+    exclusions = {PurePath(p).as_posix() for p in integration.stale_cleanup_exclusions()}
+    stale_keys = (set(old_files) - set(new_files)) - exclusions
     if stale_keys:
         stale_manifest = IntegrationManifest(key, project_root, version="stale-cleanup")
         stale_manifest._files = {k: old_files[k] for k in stale_keys}

src/specify_cli/integrations/base.py

@@ -393,6 +393,18 @@ class IntegrationBase(ABC):
         """
         return f"speckit.{template_name}.md"
 
+    def stale_cleanup_exclusions(self) -> set[str]:
+        """Return project-relative paths that upgrade must never stale-delete.
+
+        During ``integration upgrade``, files recorded in a previous manifest
+        but absent from the freshly written one are treated as stale and
+        removed.  Conditionally-tracked files (e.g. a settings file that the
+        integration merges into when it already exists, and therefore stops
+        tracking) would otherwise be deleted even though they are still
+        managed.  Subclasses list such paths here to protect them.
+        """
+        return set()
+
     def commands_dest(self, project_root: Path) -> Path:
         """Return the absolute path to the commands output directory.
 

src/specify_cli/integrations/copilot/__init__.py

@@ -282,6 +282,17 @@ class CopilotIntegration(IntegrationBase):
         """Copilot commands use ``.agent.md`` extension."""
         return f"speckit.{template_name}.agent.md"
 
+    def stale_cleanup_exclusions(self) -> set[str]:
+        """Protect ``.vscode/settings.json`` from upgrade stale-deletion.
+
+        ``setup()`` records this file in the manifest only when it creates it;
+        when it already exists the file is merged and intentionally left
+        untracked.  On upgrade the untracked-but-existing file would otherwise
+        be flagged stale and deleted, destroying user settings (and the file
+        the integration still manages).
+        """
+        return {".vscode/settings.json"}
+
     def post_process_skill_content(self, content: str) -> str:
         """Inject shared hook guidance into Copilot skill content.