Some testresults:
resolv.conf dns server*, nsswitch setting, hosts contains 127.0.1.1 entry, 
result
---------------------------------------------------------------------------------
127.0.0.53             , file resolve dns, no                            , fails
127.0.1.1              , file resolve dns, no                            , fails
127.0.0.53             , file dns        , no                            , works
127.0.1.1              , file dns        , no                            , works
127.0.0.53             , file resolve dns, yes                           , works
127.0.1.1              , file resolve dns, yes                           , works

* if 127.0.0.53, symlink to /lib/systemd/resolve.conf is in use

Conclusion: the problem is in nss_resolve

since nss_resolve should use dbus, I checked with dbus-monitor --system what is 
sent.
If you are able to reproduce this problem: To me it seems that the request is 
sent after the timeout already happened. Also while the login attempt is 
running, systemd-resolve is not working. Do you know a situation dbus-daemon is 
blocking?. If this proves true, what could cause this?

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https://bugs.launchpad.net/bugs/1764853

Title:
  winbind returns PAM_AUTHINFO_UNAVAIL on first login after reboot

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