You have been subscribed to a public bug by Simon Poirier (simpoir):

[Impact]

 * When launching an Ubuntu release-upgrade through landscape-client, the
   upgrade-tool fails GPG verification due to trusted apt key having changed
   location as of 18.04 LTS.

 * The proposed patch extends gpg lookup path to include all
   /etc/apt/trusted.gpg.d/*.gpg files in addition to /etc/apt/trusted.gpg
   when verifying the upgrade-tool signature.

[Test Case]

 * Install and register the landscape-client against a landscape-server
   on a series supporting an upgrade.

 * Wait for it to sync up packages.

 * On the computer packages page, there is a link at the bottom to request a
   release upgrade of that machine, if a supported version is available.

 * The upgrade fails and /var/log/landscape/release-upgrader.log will indicate
   a failed gpg verification.

[Where problems could occur]

 * One thing which has been considered in this fix is how someone could have
   worked around the issue by re-creating the old key path. The fix covers
   such a case by still reading the deprecated trusted.gpg file.

 * Although some care has been taken to only load valid gpg keys from apt
   trusted keychain, there could be unforeseen scenarios where invalid data
   gets read from the keychain. In such a case, the strict nature of gpg would
   reject the signature verification, thus being no worse than without the fix.

 * The affected callsite is used for verifying the release-upgrader code prior
   to running it. One bad thing which we could imagine with this code path is
   falsely accepting an invalid file signature, which may create a security
   issue. This would likely take shape of injecting a gpg key, without
   having root access, in the search path.

[Other Info]

 * There is no way to directly verify this issue on 20.10 Groovy and later
   (without faking a release) due to the lack of upgrade path to a supported
   LTS. The ubuntu-keyring package having the same file layout, the same
   validation failure is however to be expected if left unpatched.

[Original description]

Since bionic, ubuntu-keyring removed `/etc/apt/trusted.gpg` in favor of
`/etc/apt/trusted.gpg.d/`

This breaks signature verification for the upgrade-tool.
Trying to release-upgrade through landscape yields a failure on signature check:

2020-11-10 15:47:51,019 WARNING  [MainThread] Invalid signature for 
upgrade-tool tarball: /usr/bin/gpg failed (out='', err='gpg: keybox 
'/etc/apt/trusted.gpg' created
gpg: Signature made Fri Oct 16 03:28:09 2020 UTC
gpg:                using RSA key 3B4FE6ACC0B21F32
gpg: Can't check signature: No public key

** Affects: landscape-client
     Importance: High
     Assignee: Simon Poirier (simpoir)
         Status: Fix Committed

** Affects: landscape-client (Ubuntu)
     Importance: Undecided
     Assignee: Simon Poirier (simpoir)
         Status: In Progress

** Affects: landscape-client (Ubuntu Bionic)
     Importance: Undecided
     Assignee: Simon Poirier (simpoir)
         Status: In Progress

** Affects: landscape-client (Ubuntu Focal)
     Importance: Undecided
     Assignee: Simon Poirier (simpoir)
         Status: In Progress

** Affects: landscape-client (Ubuntu Groovy)
     Importance: Undecided
     Assignee: Simon Poirier (simpoir)
         Status: Won't Fix

** Affects: landscape-client (Ubuntu Hirsute)
     Importance: Undecided
     Assignee: Simon Poirier (simpoir)
         Status: In Progress

** Affects: landscape-client (Ubuntu Impish)
     Importance: Undecided
         Status: New

** Affects: landscape-client (Ubuntu Jammy)
     Importance: Undecided
     Assignee: Simon Poirier (simpoir)
         Status: In Progress

-- 
Changed ubuntu-keyring paths breaks upgrade to focal.
https://bugs.launchpad.net/bugs/1903776
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