(FAQ says to send bug reports to the debian-backports mailing list; so I'm doing so since it hasn't been sent here. Also cc'ing someone else's report in the BTS).
# certbot Traceback (most recent call last): File "/usr/bin/certbot", line 5, in <module> from pkg_resources import load_entry_point File "/usr/lib/python2.7/dist-packages/pkg_resources.py", line 2876, in <module> working_set = WorkingSet._build_master() File "/usr/lib/python2.7/dist-packages/pkg_resources.py", line 451, in _build_master return cls._build_from_requirements(__requires__) File "/usr/lib/python2.7/dist-packages/pkg_resources.py", line 464, in _build_from_requirements dists = ws.resolve(reqs, Environment()) File "/usr/lib/python2.7/dist-packages/pkg_resources.py", line 639, in resolve raise DistributionNotFound(req) pkg_resources.DistributionNotFound: psutil>=2.2.1 Neither Jessie nor Jessie-backports has a new enough python-psutil, even if the versioned Depends: were not missing. This makes me think you have accidentally forgotten to test your backport on a Jessie system or, alternatively, your Jessie system is not "clean". PS: You probably need a versioned Depends: in unstable too, since the too-old version is part of stable.