I have a situation that is similar but not with a windows server.

I have an experimental server which is installed with Ubuntu Disco.
Queues are authenticated with kerberos. This is IPP-Everywhere queues.

I have a client with Ubuntu 18.04.2 LTS.

Printing did not work with cups-2.2.7-1ubuntu2.4 on the client. Same
symptoms as described here, cannot print, authentication prompt despite
valid kerberos tickets.

I compiled upstream cups 2.2.7 with Eskos fix-password-prompt.patch AND
the kerberos truncate patch from #13 and installed it on the client.

It works, but printing is very slow, at least from firefox.

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https://bugs.launchpad.net/bugs/1783298

Title:
  [SRU] AuthInfoRequired negotiate in cups 2.2.7 in Bionic does not work

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