This bug was fixed in the package update-manager - 1:16.04.16

update-manager (1:16.04.16) xenial; urgency=medium

  * Use HTTPS for (LP: #1744318)
  * Add support for HTTPS proxies; this breaks 
    API - the return value is now a dict, rather than a string (LP: #1771914).

 -- Julian Andres Klode <>  Tue, 20 Aug 2019 13:59:31

** Changed in: update-manager (Ubuntu Xenial)
       Status: Fix Committed => Fix Released

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  release-upgrade-motd can't update message via apt proxy

Status in update-manager package in Ubuntu:
  Fix Released
Status in update-manager source package in Xenial:
  Fix Released
Status in update-manager source package in Bionic:
  Fix Released

Bug description:
  apt proxy settings are not applied to https urls, and thus the 
release-upgrade-motd script fails, and upgrades from bionic to new versions 
won't be detected either, if you need to use a proxy. This is a regression from 
the 1:18.04.6 upload which switched from http to https.

  [Test case]
  Set acquire::http::proxy to a non-existing host, e.g. 
http://invalid.invalid/, and check that the tool fails.

  Do the same with acquire::https::proxy.

  (Kind of a reverse check, since I don't have a proxy setup to test
  against. If there's an actual proxy and otherwise, no internet, it can
  be verified by setting the actual proxy and checking that it works
  with it).

  [Regression potential]
  The fix changes the API of init_proxy() in UpdateManager/Core/ to 
make it return a dict with 'http' and 'https' members rather than just a 
string. It seems the return value is only used by the test case, though, so 
that should be fine.

  Apart from that, it also allows https proxies now, since we're doing
  https anyway, which means that a proxy setting ignored before now is
  not. The same applies to the the new proxy variables used - they were
  not used before, so things might fail that used to work - like you
  specify an invalid https proxy but don't actually need one. Low risk,

  [Original bug report]
  I have configured apt proxy in apt.conf.d and apt update and apt install can 
work correctly. However, when I logged in system everyday, in the login 
message, it says:

  Failed to connect to
  Check your Internet connection or proxy settings

  After further investigation, I found the the issue is caused in
  package python3-update-manager:

  python3-update-manager: /usr/lib/python3/dist-

  In the init_proxy function of the python script, it only set a http
  proxy by below code:

  proxy_support = ProxyHandler({"http": proxy})

  after changing the line to add https proxy, it can work:

  proxy_support = ProxyHandler({"http": proxy, "https":proxy})

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