diff --git a/.jules/sentinel.md b/.jules/sentinel.md
new file mode 100644
index 0000000000..db2769425d
--- /dev/null
+++ b/.jules/sentinel.md
@@ -0,0 +1,4 @@
+## 2024-05-24 - [Insecure Random Number Generation]
+**Vulnerability:** Weak random number generation using `random.choices` for passwords and unique identifiers (e.g. root SSH password, user IDs, session IDs).
+**Learning:** `random.choices` is not cryptographically secure and predictable. It should never be used for security-sensitive operations.
+**Prevention:** Always use the `secrets` module (e.g. `secrets.choice`) for generating cryptographic or security-sensitive identifiers.
diff --git a/agent.py b/agent.py
index 267a908077..f29f0d41da 100644
--- a/agent.py
+++ b/agent.py
@@ -1,4 +1,4 @@
-import asyncio, random, string, threading
+import asyncio, random, string, threading, secrets
 
 from collections import OrderedDict
 from dataclasses import dataclass, field
@@ -135,7 +135,7 @@ def all():
     @staticmethod
     def generate_id():
         def generate_short_id():
-            return "".join(random.choices(string.ascii_letters + string.digits, k=8))
+            return "".join(secrets.choice(string.ascii_letters + string.digits) for _ in range(8))
 
         while True:
             short_id = generate_short_id()
diff --git a/helpers/guids.py b/helpers/guids.py
index f0def4b4c6..41439e4bbe 100644
--- a/helpers/guids.py
+++ b/helpers/guids.py
@@ -1,4 +1,4 @@
-import random, string
+import random, string, secrets
 
 def generate_id(length: int = 8) -> str:
-    return "".join(random.choices(string.ascii_letters + string.digits, k=length))
+    return "".join(secrets.choice(string.ascii_letters + string.digits) for _ in range(length))
diff --git a/prepare.py b/prepare.py
index a4c4af9c45..ec0fcc714d 100644
--- a/prepare.py
+++ b/prepare.py
@@ -1,6 +1,7 @@
 from helpers import dotenv, runtime, settings
 import string
 import random
+import secrets
 import sys
 from helpers.print_style import PrintStyle
 
@@ -33,7 +34,7 @@ def _retire_legacy_collabora_runtime() -> None:
     # generate random root password if not set (for SSH)
     root_pass = dotenv.get_dotenv_value(dotenv.KEY_ROOT_PASSWORD)
     if not root_pass:
-        root_pass = "".join(random.choices(string.ascii_letters + string.digits, k=32))
+        root_pass = "".join(secrets.choice(string.ascii_letters + string.digits) for _ in range(32))
         PrintStyle.standard("Changing root password...")
     settings.set_root_password(root_pass)