• kbare at CLUB.CC.CMU.EDU
• Jessie to Stretch Upgrade

WARNING: I have not yet tested cascaded wheezy -> jessie -> stretch upgrades. As such, I do not currently recommend upgrading jessie machines that previously ran wheezy.

GOOD NEWS: The same steps also appear to work for stretch -> buster and buster -> bullseye upgrades, if proper substitutions are made.

As of 8/25/2018, it works, but isn't seamless. Take the following steps:

• Add stretch-cclub repo: echo "deb http://debian.club.cc.cmu.edu/debian/ stretch-cclub contrib" >> /etc/apt/sources.list

• apt-get update

• apt-get -t stretch-cclub install cclub-fix-debian-mirror-configuration

• Change /etc/apt/apt.conf.d/90cclub APT::Default-Release to stretch-cclub

• Hold all cclub configuration packages:
  

  dpkg --get-selections | sed -e 's/^\(cclub-.*-configuration[ \t]\+\)install$/\1hold/' -e 't' -e 'd' | dpkg --set-selections

• apt-get update

• rm /var/lib/cclub-configuration/flags/passwd-update-configured

• DEBIAN_FRONTEND=noninteractive apt-get -o DPkg::options::=--force-confdef -o DPkg::options::=--force-confold dist-upgrade

• Check /etc for .dpkg-dist/.ucf-dist files for configuration that is not managed by the cclub configuration packages; fold-in the Debian changes as appropriate
  • If a configuration file is managed by the cclub configuration packages, there is usually a copy of the file under /usr/share/cclub-configuration

  • Take make this easier the next time, delete any .dpkg-dist/.ucf-dist files after you've confirmed there are not any changes that need to be folded in

• Unhold all cclub configuration packages:
  

  dpkg --get-selections | sed -e 's/^\(cclub-.*-configuration[ \t]\+\)hold$/\1install/' -e 't' -e 'd' | dpkg --set-selections

• apt-get dist-upgrade

• touch /var/lib/cclub-configuration/flags/passwd-update-configured

• Copy any newly added users (in /etc/passwd or /etc/passwd.OLD) to /etc/passwd.system no longer needed with cclub-passwd-update-configuration >= 1.2

• mv /etc/pam.d/login.dpkg-dist /etc/pam.d/login no longer needed with cclub-base-configuration >= 1.5

• dpkg-reconfigure cclub-base-configuration no longer needed with cclub-base-configuration >= 1.5

• (optional): apt-get clean

• (optional): apt-get autoremove

If we're doing upgrades like this frequently, I can look into scripting parts of the process.