Hi Matthew,

I report the complete configuration of the machine in which I see the problem.
The machine is an Optiplex 745, with an Intel Core2 6320 CPU, 4 GB RAM and a 
rotational HD, which I use as a test box for Ubuntu 22.04.
It was joined to an AD domain with the "net ads join -U aduser" command and 
uses sssd for authentication and samba and winbind for sharing folders.

The minimun number of iterations needed for the
ExecStartPre=bash -c "for i in echo {1..20} ; do if [ $(env | grep KRB5CCNAME) 
== "" ]; then sleep 0.2 ; fi ; done"
command to work is 15, so it's a delay of about 3 s.

I normally do not see the bug in my personal workstation, which runs
Ubuntu 20.04 and is a much faster machine (Ryzen 5 with nvme SSD).

>From the logs I can see that gvfsd is correctly started by systemd
--user also in all my cases; so I suspect that the problem is that, with
the slow machine, the kerberos ticket needed by gvfsd is actually
written to the hard disk with too much delay.

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You received this bug notification because you are a member of Desktop
Packages, which is subscribed to gvfs in Ubuntu.
https://bugs.launchpad.net/bugs/1779890

Title:
  Nautilus does not use a valid Kerberos ticket when accessing Samba
  share

Status in gvfs:
  Unknown
Status in gvfs package in Ubuntu:
  Triaged

Bug description:
  Nautilus prompts for username and password when accessing a Samba
  share on a network drive, despite having a perfectly valid unexpired
  Kerberos ticket. The Kerberos ticket is obtained automatically at
  logon by authentication against a Samba Active Directory server (Samba
  AD-DC).

  Accessing the same Samba share with the same Kerberos ticket via
  "smbclient //host/sharename -k" works fine.

  One known workaround is: "nautilus -q", and then "killall gvfsd".
  After that, accessing the Samba share with Nautilus works normally as
  it should.

  I did not experience this issue in Ubuntu 16.04. It appears that a
  regression was introduced somewhere between 16.04 and 18.04.

  The issue is quite annoying and confusing for the users who are used
  to accessing Samba shares on the network drive without being prompted
  for their username and password.

  The issue appears to manifest itself usually not on the first access
  to a Samba share, but on subsequent accesses after a system reboot or
  upon user logout/login. Strangely, removing ~/.cache/ibus/bus/registry
  file before user login appears to fix the issue for the current user
  session, but then the problem reappears upon subsequent user logins or
  after a system reboot.

  Nemo appears to have the same problem as Nautilus.

  ProblemType: Bug
  DistroRelease: Ubuntu 18.04
  Package: gvfs-daemons 1.36.1-0ubuntu1
  ProcVersionSignature: Ubuntu 4.15.0-24.26-generic 4.15.18
  Uname: Linux 4.15.0-24-generic x86_64
  NonfreeKernelModules: nvidia_modeset nvidia
  ApportVersion: 2.20.9-0ubuntu7.2
  Architecture: amd64
  Date: Tue Jul  3 11:12:06 2018
  ExecutablePath: /usr/lib/gvfs/gvfsd
  InstallationDate: Installed on 2018-04-27 (66 days ago)
  InstallationMedia: Ubuntu 18.04 LTS "Bionic Beaver" - Release amd64 (20180426)
  ProcEnviron:
   LANG=en_CA.UTF-8
   PATH=(custom, no user)
   SHELL=/bin/bash
   XDG_RUNTIME_DIR=<set>
  SourcePackage: gvfs
  UpgradeStatus: No upgrade log present (probably fresh install)

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