Here's a simplified Python script (henceforth app.py) that forks a child which then runs a subprocess: import os import subprocess if os.fork() > 0: os._exit(0) subprocess.run(["/bin/true"]) When run as a normal user, it works: $ python3 app.py $ echo $? 0 When run as root from a sudo-launched parent shell, it works: $ sudo bash # python3 app.py # However when the parent is sudo, it fails in a bizarre way: $ sudo python3 app.py $ Traceback (most recent call last): File "/tmp/app.py", line 7, in <module> subprocess.run(["/bin/true"]) File "/usr/lib/python3.11/subprocess.py", line 548, in run with Popen(*popenargs, **kwargs) as process: ^^^^^^^^^^^^^^^^^^^^^^^^^^^ File "/usr/lib/python3.11/subprocess.py", line 1026, in __init__ self._execute_child(args, executable, preexec_fn, close_fds, File "/usr/lib/python3.11/subprocess.py", line 1955, in _execute_child raise child_exception_type(errno_num, err_msg, err_filename) OSError: [Errno 38] Function not implemented: '/bin/true' and: $ sudo bash # exec python3 app.py $ Traceback ... (same error message as above) Apparently something in the child process created by subprocess.run it getting ENOSYS, but it's a mystery to me how having sudo as the parent can cause this. Update: The system in question is TrueNAS SCALE (Debian-derived Linux) with Python 3.11.9. Since posting I discovered that this does not repro on another Linux system, so I now suspect it is somehow related to sudo configuration or kernel security options. Continue reading...