diff --git a/dissect/target/tools/shell.py b/dissect/target/tools/shell.py
index 175f960fcb..7185f57ce7 100644
--- a/dissect/target/tools/shell.py
+++ b/dissect/target/tools/shell.py
@@ -9,6 +9,7 @@
 import logging
 import os
 import pathlib
+import platform
 import pydoc
 import random
 import re
@@ -1442,6 +1443,20 @@ def main() -> None:
     if args.quiet:
         logging.getLogger("dissect").setLevel(level=logging.ERROR)
 
+    # PyPy < 3.10.14 readline is stuck in Python 2.7
+    if platform.python_implementation() == "PyPy":
+        major, minor, patch = tuple(map(int, platform.python_version_tuple()))
+        if major <= 3 and minor <= 10 and patch < 14:
+            print(
+                "\n".join(
+                    [
+                        "Note for users of PyPy < 3.10.14:",
+                        "Autocomplete might not work due to an outdated version of pyrepl/readline.py",
+                        "To fix this, please update your version of PyPy.",
+                    ]
+                )
+            )
+
     try:
         open_shell(args.targets, args.python, args.registry)
     except TargetError as e: