diff --git a/src/specify_cli/__init__.py b/src/specify_cli/__init__.py
index 83d2fdf87..2959e636e 100644
--- a/src/specify_cli/__init__.py
+++ b/src/specify_cli/__init__.py
@@ -32,6 +32,7 @@
 import json
 from pathlib import Path
 from typing import Optional, Tuple
+from enum import Enum
 
 import typer
 import httpx
@@ -62,6 +63,27 @@ def _github_auth_headers(cli_token: str | None = None) -> dict:
     token = _github_token(cli_token)
     return {"Authorization": f"Bearer {token}"} if token else {}
 
+def _confirm_overwrite(item: Path) -> bool:
+    prompt = f"[bright_blue]{str(item)}[/bright_blue] exists. Overwrite it with a template?"
+    keep = OverwriteOptionsEnum.KEEP.value
+    OVERWRITE_OPTIONS[keep] = OVERWRITE_OPTIONS[keep].format(item.name)
+
+    result = select_with_arrows(
+        OVERWRITE_OPTIONS,
+        prompt_text=prompt,
+        default_key=OverwriteOptionsEnum.OVERWRITE.value,
+    )
+
+    if result is OverwriteOptionsEnum.OVERWRITE.value:
+        return True
+    return False
+
+def _overwrite_is_allowed(item: Path, force: bool = False) -> bool:
+    if not force and str(item) in FILES_TO_CONFIRM_OVERWRITING:
+        if not _confirm_overwrite(item):
+            return False
+    return True
+
 # Constants
 AI_CHOICES = {
     "copilot": "GitHub Copilot",
@@ -82,6 +104,17 @@ def _github_auth_headers(cli_token: str | None = None) -> dict:
 # Claude CLI local installation path after migrate-installer
 CLAUDE_LOCAL_PATH = Path.home() / ".claude" / "local" / "claude"
 
+class OverwriteOptionsEnum(Enum):
+    OVERWRITE = "Overwrite"
+    KEEP = "Keep"
+
+OVERWRITE_OPTIONS = {
+    OverwriteOptionsEnum.OVERWRITE.value: "Proceed with overwriting",
+    OverwriteOptionsEnum.KEEP.value: "Keep [blue]{}[/blue] and proceed",
+}
+
+FILES_TO_CONFIRM_OVERWRITING = ["memory/constitution.md"]
+
 # ASCII Art Banner
 BANNER = """
 ███████╗██████╗ ███████╗ ██████╗██╗███████╗██╗   ██╗
@@ -543,7 +576,7 @@ def download_template_from_github(ai_assistant: str, download_dir: Path, *, scri
     return zip_path, metadata
 
 
-def download_and_extract_template(project_path: Path, ai_assistant: str, script_type: str, is_current_dir: bool = False, *, verbose: bool = True, tracker: StepTracker | None = None, client: httpx.Client = None, debug: bool = False, github_token: str = None) -> Path:
+def download_and_extract_template(project_path: Path, ai_assistant: str, script_type: str, is_current_dir: bool = False, *, verbose: bool = True, tracker: StepTracker | None = None, client: httpx.Client = None, debug: bool = False, github_token: str = None, force: bool = False) -> Path:
     """Download the latest release and extract it to create a new project.
     Returns project_path. Uses tracker if provided (with keys: fetch, download, extract, cleanup)
     """
@@ -631,6 +664,7 @@ def download_and_extract_template(project_path: Path, ai_assistant: str, script_
                                     if sub_item.is_file():
                                         rel_path = sub_item.relative_to(item)
                                         dest_file = dest_path / rel_path
+                                        if not _overwrite_is_allowed(rel_path, force): continue
                                         dest_file.parent.mkdir(parents=True, exist_ok=True)
                                         shutil.copy2(sub_item, dest_file)
                             else:
@@ -965,7 +999,7 @@ def init(
             local_ssl_context = ssl_context if verify else False
             local_client = httpx.Client(verify=local_ssl_context)
 
-            download_and_extract_template(project_path, selected_ai, selected_script, here, verbose=False, tracker=tracker, client=local_client, debug=debug, github_token=github_token)
+            download_and_extract_template(project_path, selected_ai, selected_script, here, verbose=False, tracker=tracker, client=local_client, debug=debug, github_token=github_token, force=force)
 
             # Ensure scripts are executable (POSIX)
             ensure_executable_scripts(project_path, tracker=tracker)