diff --git a/starpunk/media.py b/starpunk/media.py
index 216ccee..2a8073a 100644
--- a/starpunk/media.py
+++ b/starpunk/media.py
@@ -122,13 +122,19 @@ def validate_image(file_data: bytes, filename: str) -> Tuple[bytes, str, int, in
                 # Mark as HEIF so conversion happens below
                 img.format = 'HEIF'
             except Exception as heic_error:
-                # Log the magic bytes for debugging (if in app context)
+                # Log the magic bytes and save file for debugging (if in app context)
                 try:
                     magic = file_data[:12].hex() if len(file_data) >= 12 else file_data.hex()
                     current_app.logger.warning(
                         f'Media upload failed both Pillow and HEIC: filename="{filename}", '
                         f'magic_bytes={magic}, pillow_error="{e}", heic_error="{heic_error}"'
                     )
+                    # Save failed file for analysis
+                    debug_dir = Path(current_app.config.get('DATA_PATH', 'data')) / 'debug'
+                    debug_dir.mkdir(parents=True, exist_ok=True)
+                    debug_file = debug_dir / f"failed_{datetime.now().strftime('%Y%m%d_%H%M%S')}_{filename}"
+                    debug_file.write_bytes(file_data)
+                    current_app.logger.info(f'Saved failed upload for analysis: {debug_file}')
                 except RuntimeError:
                     pass  # Outside app context (e.g., tests)
                 raise ValueError(f"Invalid or corrupted image: {e}")