diff --git a/src/specify_cli/_utils.py b/src/specify_cli/_utils.py
index beae253593..d009f25866 100644
--- a/src/specify_cli/_utils.py
+++ b/src/specify_cli/_utils.py
@@ -183,13 +183,13 @@ def atomic_write_json(target_file: Path, payload: dict[str, Any]) -> None:
             else:
                 log("Skipped merge (preserved existing settings)", "yellow")
         else:
-            shutil.copy2(sub_item, dest_file)
+            shutil.copyfile(sub_item, dest_file)
             log("Copied (no existing settings.json):", "blue")
 
     except Exception as e:
         log(f"Warning: Could not merge settings: {e}", "yellow")
         if not dest_file.exists():
-            shutil.copy2(sub_item, dest_file)
+            shutil.copyfile(sub_item, dest_file)
 
 
 def merge_json_files(existing_path: Path, new_content: Any, verbose: bool = False) -> dict[str, Any] | None:
@@ -272,6 +272,24 @@ def deep_merge_polite(base: dict[str, Any], update: dict[str, Any]) -> dict[str,
     return merged
 
 
+def ensure_writable_tree(path: Path) -> None:
+    """Add owner write+execute to every directory under path.
+
+    shutil.copytree always calls copystat() on directories, propagating
+    read-only bits from any read-only source. Call this after copytree to
+    guarantee destination directories accept writes regardless of source
+    permissions.
+    """
+    if os.name == "nt":
+        return
+    for dirpath, _, _ in os.walk(path):
+        dp = Path(dirpath)
+        try:
+            dp.chmod(dp.stat().st_mode | 0o300)
+        except OSError:
+            pass
+
+
 def _display_project_path(project_root: Path, path: str | Path) -> str:
     """Return a stable POSIX-style display path for paths under a project."""
     path_obj = Path(path)
diff --git a/src/specify_cli/commands/init.py b/src/specify_cli/commands/init.py
index 68f5bed31f..4a606ab970 100644
--- a/src/specify_cli/commands/init.py
+++ b/src/specify_cli/commands/init.py
@@ -430,7 +430,7 @@ def init(
                             import shutil as _shutil
                             dest_wf = project_path / ".specify" / "workflows" / "speckit"
                             dest_wf.mkdir(parents=True, exist_ok=True)
-                            _shutil.copy2(
+                            _shutil.copyfile(
                                 bundled_wf / "workflow.yml",
                                 dest_wf / "workflow.yml",
                             )
diff --git a/src/specify_cli/extensions.py b/src/specify_cli/extensions.py
index bddf637cbc..a9ce528709 100644
--- a/src/specify_cli/extensions.py
+++ b/src/specify_cli/extensions.py
@@ -27,6 +27,7 @@
 
 from .catalogs import CatalogEntry as BaseCatalogEntry, CatalogStackBase
 from ._init_options import is_ai_skills_enabled
+from ._utils import ensure_writable_tree
 
 _FALLBACK_CORE_COMMAND_NAMES = frozenset({
     "analyze",
@@ -1280,7 +1281,8 @@ def install_from_directory(
             shutil.rmtree(dest_dir)
 
         ignore_fn = self._load_extensionignore(source_dir)
-        shutil.copytree(source_dir, dest_dir, ignore=ignore_fn)
+        shutil.copytree(source_dir, dest_dir, ignore=ignore_fn, copy_function=shutil.copyfile)
+        ensure_writable_tree(dest_dir)
 
         # Register commands with AI agents
         registered_commands = {}
diff --git a/src/specify_cli/presets.py b/src/specify_cli/presets.py
index 47b4240d85..4c93651c79 100644
--- a/src/specify_cli/presets.py
+++ b/src/specify_cli/presets.py
@@ -30,6 +30,7 @@
 from .extensions import REINSTALL_COMMAND, ExtensionRegistry, normalize_priority
 from .integrations.base import IntegrationBase
 from ._init_options import is_ai_skills_enabled
+from ._utils import ensure_writable_tree
 
 
 def _substitute_core_template(
@@ -1534,7 +1535,8 @@ def install_from_directory(
         if dest_dir.exists():
             shutil.rmtree(dest_dir)
 
-        shutil.copytree(source_dir, dest_dir)
+        shutil.copytree(source_dir, dest_dir, copy_function=shutil.copyfile)
+        ensure_writable_tree(dest_dir)
 
         # Pre-register the preset so that composition resolution can see it
         # in the priority stack when resolving composed command content.