diff --git a/personal/cron_scripts/system/update_system.py b/personal/cron_scripts/system/update_system.py
index 7a95d33..baac2d4 100644
--- a/personal/cron_scripts/system/update_system.py
+++ b/personal/cron_scripts/system/update_system.py
@@ -1,15 +1,45 @@
 #!/usr/bin/python3
 import subprocess
 import os
+from datetime import datetime, timezone
+from typing import Optional
 
+
+def generate_timestamp(fmt: Optional[str] = None, utc: bool = False) -> str:
+    """Return a timestamp string.
+
+    - If `fmt` is provided, return `datetime.strftime(fmt)`.
+    - If `fmt` is None, return an ISO 8601 timestamp. When `utc` is True
+      the timestamp ends with 'Z' (UTC). When `utc` is False it returns
+      the local time ISO format.
+
+    Examples:
+      - `generate_timestamp()` -> '2025-11-20T12:34:56Z'
+      - `generate_timestamp("%Y-%m-%d %H:%M:%S")` -> '2025-11-20 12:34:56'
+    """
+    if fmt:
+        dt = datetime.now(timezone.utc) if utc else datetime.now()
+        return dt.strftime(fmt)
+
+    dt = datetime.now(timezone.utc) if utc else datetime.now()
+    if utc:
+        # force trailing Z for UTC instead of +00:00
+        return dt.replace(tzinfo=timezone.utc).isoformat().replace('+00:00', 'Z')
+    return dt.isoformat()
+
+print(f"Starting system update at {generate_timestamp()}")
 # Update package lists
+print(f"{generate_timestamp()}: Updating package lists...")
 subprocess.run(['sudo', 'apt', 'update'], check=True)
 # Upgrade packages
+print(f"{generate_timestamp()}: Upgrading packages...")
 subprocess.run(['sudo', 'apt', 'upgrade', '-y'], check=True)
 
 # Check if reboot is required
 if os.path.exists('/var/run/reboot-required'):
-    print("Reboot required. Rebooting now...")
+    print(f"{generate_timestamp()}: Reboot required. Rebooting now...")
     subprocess.run(['sudo', 'reboot'])
 else:
-    print("No reboot required.")
+    print(f"{generate_timestamp()}: No reboot required.")
+
+