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Comment by doublepg23 | Hacker News Reader

Maybe someone here would have advice for upgrading ancient OpenBSD installs?

I inherited some 5.x OpenBSD systems at my current job and I'm really curious how I'd go about upgrading to 7.4 - I have a feeling I'll be running into some broken links.

I'd really like to meet the person who was gung-ho enough to use OpenBSD in prod but seemingly treated them like a LTS system - not a "releases are supported for ~1 year" system.

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Every release has an upgrade guide, like this: https://www.openbsd.org/faq/upgrade74.html

Make backups, make sure you can restore them, then just step through it one version at a time. Things got a lot easier around 6.6 when sysupgrade was introduced.

Luckily, I believe a lot of the applications are our own and the rest are in base or with a good upgrade path (nginx).

My only concern is if I'll find missing packages for such old releases - I guess that's nothing a VM wouldn't show though.

It looks like some mirrors have packages going way back (http://ftp.eu.openbsd.org/pub/OpenBSD/), but depending on your use-case, it may be more beneficial to focus on the base system upgrades (documented in the upgrade guide) and worry about the packages later.

That many years of package changes could be troublesome to deal with, and it may be better to fast-forward to whatever the modern tooling would be.

I believe that's the case too.

However speaking with my manager I think the long term plan is to dump it for RHEL - too bad because I'd like it on my resume :-) Not every day you can play with OpenBSD in prod - usually it's just on my oddball computers.

It's possible, but you'll run into annoying breakage long the way. It's probably safer and less troublesome (unless you're deeply familiar with the changes along the way and the old upgrade procedures) to take the existing configurations as guidelines what to recreate on the latest release.

Probably the best method. I believe most applications our either our own (some Golang tools, for some reason?) or basic base applications (migration to relayd instead of nginx as a proxy is probably a good idea.)

What are you using them for? I feel a lot more comfortable using OpenBSD in production than Linux for the long-term (my personal opinion). I've been using it since ~3.5, and the 6 months releases have been ticking along nearly flawlessly for a long, long time.

Yes I feel like OpenBSD can be a great system for this use case, but the prior owner of this system had neglected it. Now it's still on 5.6 and who knows how much cruft has built up.

It's currently acting as a bridge system that translates 5010 X12s to 4010 and vice versa. Strangely enough the whole stack in Golang which I don't believe considers OpenBSD to be a supported platform?

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