Back when I looked at OpenBSD a decade ago, I liked the OS but upgrading from one version to the next seemed to be problematic. Anybody had any experiences (good or bad) with upgrading modern OpenBSD?
Upgrading OpenBSD is as transparent as it gets. Put a new kernel in place, extract the install sets, run sysmerge to update /etc and X configuration and you're done.
The FAQ has a very cautious explanation of the whole process, pointing out every imaginable pitfall. Once you've done it, it's a five minute job on most standard installations.
The official recommendation is to boot the installation kernel and upgrade that way, but I've never had a problem doing a remote upgrade. It's always been entirely painless.
One could argue that it's not quite as simple as "apt-get dist-upgrade" but I like it better - the upgrade process is more explicit about not touching your config files. And since it's a BSD, the base system isn't packaged, so I'm not entirely sure how it would work (although FreeBSD does have freebsd-update now, so it's possible).
Thanks for the details. On Linux the upgrade process can be problematic depending on which distro you're using and how wrenching the upgrades are to the various packages you're relying on, but I must admit I've been spoiled by Debian's apt-get dist-upgrade. Good to hear that with a little experience, OpenBSD's upgrade can be similarly stable.
OpenBSD's way for system upgrades is so easy: unzip tarballs, run /etc diff, reboot. Its always astonishing how simple and carefree it is to upgrade to the next major.
Contrary to that, most companies would never upgrade a linux system. My feeling is, the most used "upgrade" plan for debian is to not upgrade as long as possible and then do a full reinstall with a new version.