tags 52269 patch thanks Hi! The following patch fixes it. I used site.addsitedir but ensured the correct ordering of sys.path (we need to make the Guix-installed packages appear before Python's own site-packages directory otherwise we wouldn't be able to override its bundled packages such as 'pip'). Here's how I tested: Copy the sitecustomize.py file to the current directory, then: --8<---------------cut here---------------start------------->8--- $ pip --version pip 21.1.3 from $HOME/.guix-profile/lib/python3.9/site-packages/pip (python 3.9) $ guix show python-pip | recsel -p version version: 20.2.4 --8<---------------cut here---------------end--------------->8--- Ensure installed pip still overrides Python's own. PYTHONPATH=. forces the sitecustomize.py file in the CWD to take precedence over the one currently installed along Python. --8<---------------cut here---------------start------------->8--- $ guix shell --pure python python-pip python-pdbpp [env]$ PYTHONPATH=. python3 -c 'import pip; print(pip.__version__)' 20.2.4 --8<---------------cut here---------------end--------------->8--- Next I created a dummy script to trigger run pdb: #file: test.py print('hello') import pdb; pdb.set_trace() --8<---------------cut here---------------start------------->8--- $ guix shell --pure python python-pip python-pdbpp [env]$ python3 test.py hello > /tmp/toto/test.py(7)() -> exit(1) (Pdb) --8<---------------cut here---------------end--------------->8--- This is the current bug; this is the regular Pdb, not Pdbpp. Let's force our revised sitecustomize.py file: --8<---------------cut here---------------start------------->8--- $ PYTHONPATH=. python3 test.py hello [0] > /tmp/toto/test.py(7)() -> exit(1) (Pdb++) --8<---------------cut here---------------end--------------->8--- Better!