[Bug 1888058] Re: Got “Authentication failed” while running do-release-upgrade from 19.10 to 20.04 LTS with proxy configured

[Ubuntu QA Website]

This bug has been reported on the Ubuntu ISO testing tracker.

A list of all reports related to this bug can be found here:
http://iso.qa.ubuntu.com/qatracker/reports/bugs/1888058

** Tags added: iso-testing

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https://bugs.launchpad.net/bugs/1888058

Title:
  Got “Authentication failed” while running do-release-upgrade from
  19.10 to 20.04 LTS with proxy configured

Status in ubuntu-release-upgrader package in Ubuntu:
  New

Bug description:
  I'm running `squid-deb-proxy` server in my local network. It works
  well for all package downloads while running all APT commands. It is
  configured for all possible known URLs of the mirrors including *old-
  releases*. The Ubuntu 19.10 client has installed client side - the
  `squid-deb-proxy-client` package.

  ```
  $ dpkg -l squid-deb-proxy-client | tail -n1
  ii  squid-deb-proxy-client 0.8.14+nmu2  all          automatic proxy discovery for APT based on Avahi

  $ sudo apt update 
  Hit:1 http://archive.ubuntu.com/ubuntu eoan InRelease
  Hit:2 http://archive.ubuntu.com/ubuntu eoan-updates InRelease
  Hit:3 http://archive.ubuntu.com/ubuntu eoan-backports InRelease
  Hit:4 http://security.ubuntu.com/ubuntu eoan-security InRelease
  Reading package lists... Done
  Building dependency tree       
  Reading state information... Done
  All packages are up to date.
  ```

  But when I try to start upgrade process to get 20.04 LTS - using `sudo
  do-release-upgrade` in the terminal I got the following error message:

  ```
  $ sudo do-release-upgrade 
  Checking for a new Ubuntu release
  Your Ubuntu release is not supported anymore.
  For upgrade information, please visit:
  http://www.ubuntu.com/releaseendoflife

  Get:1 Upgrade tool signature [1 554 B]                                                                                                              
  Get:2 Upgrade tool [1 342 kB]                                                                                                                       
  Fetched 1 343 kB in 0s (0 B/s)                                                                                                                      
  authenticate 'focal.tar.gz' against 'focal.tar.gz.gpg' 
  Authentication failed
  Authenticating the upgrade failed. There may be a problem with the network or with the server. 
  ```

  I do not see anything special in the logs on `squid-deb-proxy` server
  side:

  ```
  ==> /var/log/squid-deb-proxy/access.log <==
  1595069772.862    212 192.168.3.47 TCP_MISS/200 3349 CONNECT changelogs.ubuntu.com:443 - HIER_DIRECT/91.189.95.15 -
  1595069774.726      2 192.168.3.47 TCP_MEM_HIT/200 1950 GET http://archive.ubuntu.com/ubuntu/dists/focal-updates/main/dist-upgrader-all/current/focal.tar.gz.gpg - HIER_NONE/- application/x-gzip
  1595069775.410    681 192.168.3.47 TCP_HIT/200 1342082 GET http://archive.ubuntu.com/ubuntu/dists/focal-updates/main/dist-upgrader-all/current/focal.tar.gz - HIER_NONE/- application/x-gzip
  ```

  How should I fix the problem with *Authentication failed* to run the
  upgrade through proxy server normally? I do not want to switch proxy
  server (or exclude its configuration from the client) off to fix the
  problem.

  ---

  The results does not depend on proxy configuration method - the
  "Authentication failed" message is shown for both `squid-deb-proxy-
  client` avahi-based package and for `Acquire::http::Proxy` in
  `apt.conf`.

  Note: previous versions do not suffer from this bug. I have
  successfully upgraded 16.04 LTS to 18.04 LTS with enabled proxy. But
  the upgrade from 18.04 LTS to 19.10 and from 18.04 LTS to 20.04 LTS is
  now impossible because of the "Authentication failed" message.

  ProblemType: Bug
  DistroRelease: Ubuntu 19.10
  Package: ubuntu-release-upgrader-core 1:19.10.15.4
  ProcVersionSignature: Ubuntu 5.3.0-62.56-generic 5.3.18
  Uname: Linux 5.3.0-62-generic x86_64
  ApportVersion: 2.20.11-0ubuntu8.9
  Architecture: amd64
  CrashDB: ubuntu
  CurrentDesktop: MATE
  Date: Sat Jul 18 16:53:01 2020
  InstallationDate: Installed on 2019-10-19 (273 days ago)
  InstallationMedia: Ubuntu-MATE 19.10 "Eoan Ermine" - Release amd64 (20191017)
  PackageArchitecture: all
  SourcePackage: ubuntu-release-upgrader
  UpgradeStatus: No upgrade log present (probably fresh install)

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