Whenever my OS hits its EOL. For desktop computers: typically i use either Windows, or some Ubuntu derivative (typically with XFCE), so both are pretty long te

Whenever my OS hits its EOL. For desktop computers: typically i use either Windows, or some Ubuntu derivative (typically with XFCE), so both are pretty long term options with regular updates. Might ditch Windows 10 after it hits EOL and move over to just Linux, or maybe just use Windows 10 without networking for older games (in lieu of finding a better solution, like a VM with GPU passthrough because the old games that i like refuse to run on Linux without significant effort). For servers: same reasoning, previously i ran CentOS (RIP), but nowadays it's also either Debian or Ubuntu. Right now i'm thinking of trying out Debian LTS (community effort over at https://www.debian.org/lts/ https://www.debian.org/lts/) and afterwards just migrating over to Ubuntu across all of my nodes because the longer release cycle is more favourable for my needs. Then again, i primarily use my servers as just hosts for Docker containers, so i can have clear separation between the software and its versions that i need, as well as have more flexibility in regards to a compartmentalized setup where i might want 10 different versions on MySQL with resource limits for each, for all sorts of stable software. Thus, if i ever need to use something old/EOL as well, i can just throw it into a container and (slightly) mitigate the possible fallout. Relatively little automation to speak of currently because of how simple everything is: fail2ban, Zabbix, Docker Swarm/Kubernetes cluster join, sometimes ddclient and a bunch of tools, sometimes additional setup for backups and additional HDDs (in homelab, not for cloud VPSes). Would introduce Ansible otherwise, like i have at my workplace. In short: whatever the EOL is for the device (currently ~5 years for most), though i focus on a stable and vaguely secure baseline over bringing over my exact configuration, the latter doesn't matter to me much. Then again, i don't rice my desktop either and treat everything as a boring set of tools to solve problems with.