I upgraded my last major machine from Jessie to Stretch last week. That machine was the one running the most services, but I’d made notes while updating various others to ensure it went smoothly. Below are the things I noted along the way, both for my own reference and in case they are of use to anyone else.

  • Roundcube with the sqlite3 backend stopped working after the upgrade; fix was to edit /etc/roundcube/debian-db-roundcube.php and change sqlite3:// to sqlite:// in the $config['db_dsnw'] line.
  • Dovecot no longer supports SSLv2 so had to remove !SSLv2 from the ssl_protocols list in /etc/dovecot/conf.d/10-ssl.conf
  • Duplicity now tries to do a mkdir so I had to change from the scp:// backend to the sftp:// backend in my backup scripts.
  • Needed to add needs_root_rights=yes to /etc/X11/Xwrapper.config so Kodi systemd unit could still start it on a new VT. Need to figure out how to get this working without the need for root.
  • Upgrading fail2ban would have been easier if I’d dropped my additions in /etc/fail2ban/jail.d/ rather than the master config. Fixed for next time.
  • ejabberd continues to be a pain; I do wonder if it’s worth running an XMPP server these days. I certainly don’t end up using it to talk to people myself.
  • Upgrading 1200+ packages takes a long time, even when the majority of them don’t have any questions to ask during the process.
  • PostgreSQL upgrades have got so much easier. pg_upgradecluster 9.4 main chugged away but did exactly what I needed.

Other than those points things were pretty smooth. Nice work by all those involved!