[Bug 2080940] Re: unattended-upgrades broken by python-upgrade

[Julian Andres Klode]

While we're debating workarounds, to note:

This issue affects unattended-upgrades only once, in a non-default
configuration and does not break the ability to install upgrades. After
the upgrade ran, the next upgrade will work correctly (as it will have
imported the new email.errors due to restarting).

This may not just affect unattended-upgrades. Third-party applications
may be affected if

1. they use email.message to send or generate emails, and
2. they have not send an email prior to the update, and
3. they want to send an email after the update

Their failure case may be worse in that they graciously handle failure
and end up not crashing, and need a manual restart to be able to send
emails again.

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https://bugs.launchpad.net/bugs/2080940

Title:
  unattended-upgrades broken by python-upgrade

Status in python3.10 package in Ubuntu:
  New
Status in python3.12 package in Ubuntu:
  New
Status in python3.8 package in Ubuntu:
  New
Status in unattended-upgrades package in Ubuntu:
  Won't Fix

Bug description:
  at least focal and jammy are affected
  automatic updates installed "python3.10:amd64 3.10.12-1~22.04.6" tonight. This updated does not contain functions/classes required by unattended-upgrade. It resulted in broken status-emails for me, otherwise I would not have seen.

  One could argue that the bug is with python3.10, since there should be
  no breaking changes in LTS.

  Sep 17 06:05:01 xxx systemd[1]: Starting Daily apt upgrade and clean activities...
  Sep 17 06:05:24 xxx apt.systemd.daily[1894012]: Traceback (most recent call last):
  Sep 17 06:05:24 xxx apt.systemd.daily[1894012]:   File "/usr/bin/unattended-upgrade", line 2005, in main
  Sep 17 06:05:24 xxx apt.systemd.daily[1894012]:     send_summary_mail(res.pkgs, res.success, res.result_str,
  Sep 17 06:05:24 xxx apt.systemd.daily[1894012]:   File "/usr/bin/unattended-upgrade", line 1509, in send_summary_mail
  Sep 17 06:05:24 xxx apt.systemd.daily[1894012]:     ret = _send_mail_using_sendmail(from_email, to_email, subject, body)
  Sep 17 06:05:24 xxx apt.systemd.daily[1894012]:   File "/usr/bin/unattended-upgrade", line 1408, in _send_mail_using_sendmail
  Sep 17 06:05:24 xxx apt.systemd.daily[1894012]:     sendmail.stdin.write(msg.as_string())
  Sep 17 06:05:24 xxx apt.systemd.daily[1894012]:   File "/usr/lib/python3.10/email/message.py", line 151, in as_string
  Sep 17 06:05:24 xxx apt.systemd.daily[1894012]:     from email.generator import Generator
  Sep 17 06:05:24 xxx apt.systemd.daily[1894012]:   File "/usr/lib/python3.10/email/generator.py", line 17, in <module>
  Sep 17 06:05:24 xxx apt.systemd.daily[1894012]:     from email.errors import HeaderWriteError
  Sep 17 06:05:24 xxx apt.systemd.daily[1894012]: ImportError: cannot import name 'HeaderWriteError' from 'email.errors' (/usr/lib/python3.10/email/errors.py)

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