diff --git a/gemini/gemini.py b/gemini/gemini.py
index 6ba3d8f..807ed84 100644
--- a/gemini/gemini.py
+++ b/gemini/gemini.py
@@ -34,7 +34,6 @@ def main():
     client = genai.Client()
     context_data = {"file_ids": [], "cache_id": None}
 
-    # Load existing context if a context file is specified and exists
     if args.context and os.path.exists(args.context):
         try:
             with open(args.context, "r") as f:
@@ -68,11 +67,11 @@ def main():
         print("Cleanup complete.")
         return
 
-    # Wrap the main execution in a try/finally to guarantee cleanup on transient runs
     try:
         # ---------------------------------------------------------
         # UPLOAD LOGIC
         # ---------------------------------------------------------
+        new_files_added = False
         if args.files:
             for file_path in args.files:
                 if not os.path.exists(file_path):
@@ -85,6 +84,7 @@ def main():
                 
                 if uploaded_file.name not in context_data["file_ids"]:
                     context_data["file_ids"].append(uploaded_file.name)
+                    new_files_added = True
 
             if args.context:
                 with open(args.context, "w") as f:
@@ -94,15 +94,21 @@ def main():
         # CACHE CREATION LOGIC
         # ---------------------------------------------------------
         system_instruction = (
-#        "You are a strict data extraction tool. Output exactly what is requested "
-#        "(e.g., CSV). Never use markdown formatting blocks (like ```csv). "
-#        "Never include conversational text, greetings, or explanations. Output raw data only."
-        "You are a hybrid data extraction tool. If a specific format or file format output is requested "
-        "(e.g., CSV), then output exactly what was requested and never use markdown formatting blocks (like ```csv). "
-        "If a specific format was requested, never include conversational text, greetings, or explanations; "
-        "and output raw data only. If not specific data format is suggested, you can answer with conversational text."
+            "You are a hybrid data extraction tool. If a specific format or file format output is requested "
+            "(e.g., CSV), then output exactly what was requested and never use markdown formatting blocks (like ```csv). "
+            "If a specific format was requested, never include conversational text, greetings, or explanations; "
+            "and output raw data only. If not specific data format is suggested, you can answer with conversational text."
         )
 
+        # If new files were added but a cache already exists, we must destroy the stale cache.
+        if new_files_added and context_data.get("cache_id"):
+            print("New files detected. Destroying stale cache to rebuild...")
+            try:
+                client.caches.delete(name=context_data["cache_id"])
+            except Exception as e:
+                print(f"Warning: Could not delete stale cache. {e}", file=sys.stderr)
+            context_data["cache_id"] = None
+
         cache_too_small = False
         file_objects = []