Tested with 1.5ubuntu3.18.10.3 on Cosmic:

https://launchpadlibrarian.net/416582074/buildlog_ubuntu-cosmic-amd64.unattended-upgrades_1.5ubuntu3.18.10.3_BUILDING.txt.gz
 :
...
OK
Running ./test_rewind.py with python3
DEBUG:root:APT::VersionedKernelPackages is not set
DEBUG:root:adjusting candidate version: test-package=2.0
...

OK
...


** Tags removed: verification-needed verification-needed-bionic 
verification-needed-cosmic
** Tags added: verification-done verification-done-bionic 
verification-done-cosmic

** Also affects: unattended-upgrades (Ubuntu Xenial)
   Importance: Undecided
       Status: New

** Changed in: unattended-upgrades (Ubuntu Xenial)
       Status: New => In Progress

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https://bugs.launchpad.net/bugs/1820888

Title:
  unattended-upgrades may hold back upgrades due to comparing package
  versions by their string representation

Status in unattended-upgrades package in Ubuntu:
  Fix Released
Status in unattended-upgrades source package in Xenial:
  In Progress
Status in unattended-upgrades source package in Bionic:
  Fix Committed
Status in unattended-upgrades source package in Cosmic:
  Fix Committed

Bug description:
  [Impact]

   * Without the fix u-u could not upgrade particular packages from -security. 
It could be observed in Cosmic with systemd security updates failing to install 
partly due to 239-7ubuntu10.10 being smaller than 239-7ubuntu10.8 when 
comparing them as strings:
  
https://objectstorage.prodstack4-5.canonical.com/v1/AUTH_77e2ada1e7a84929a74ba3b87153c0ac/autopkgtest-disco/disco/amd64/u/unattended-upgrades/20190318_182031_fe4fe@/log.gz

  [Test Case]

   * The fix includes the extension of the build-time test cases to
  cover package sets with which u-u fails with without the fallback:

  ...
  Running ./test_rewind.py with python3
  DEBUG:root:APT::VersionedKernelPackages is not set
  DEBUG:root:adjusting candidate version: test-package=2.0
  ...

  With the unfixed version the test case fails here because u-u tries to
  upgrade test-package to version 12.0 because it does not find version
  2.0 smaller.

  [Regression Potential]

  * The change is very small and isolated, but fixing it revealed the
  issue fixed in LP: #1821101. Since the found issue's fix introduces
  fallbacks when apt's resolver can't find a the solution it is unlikely
  that other failures are triggered by the fix.

To manage notifications about this bug go to:
https://bugs.launchpad.net/ubuntu/+source/unattended-upgrades/+bug/1820888/+subscriptions

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