OpenBSD: Upgrade anxiety

My main laptop has been running OpenBSD 4.4 for a few months now, and that laptop has pretty much become my main PC for getting things done both at home and at the office.

And I've been quite happy with the stability and performance of the operating system as well as the applications I've installed from packages and ports. I'm using things like Firefox, Opera, Pidgin, Thunderbird, Geany, Nano, vi, OpenOffice, the GIMP, gFTP, Rox-filer, Xpdf, Adobe Reader (yep, I added it from ports) ... and really that's enough to keep me going day to day.

My anxiety comes from upgrading. OpenBSD is on a six-month upgrade cycle. Version 4.5 will be out in May. While I've been using OpenBSD off and on since 4.2, I've only done one upgrade, from 4.2 to 4.3, and while it wasn't the most painful experience, neither was it as easy as firing up Synaptic or running apt-get update apt-get upgrade in Debian. Not by a long shot.

As I recall, the system is able to update all of the applications installed as precompiled packages. But now I'm using a few selected ports (applications that are either fetched from other sites in binary form and installed in OpenBSD for reasons of licensing, or that are fetched in source form and compiled on the system). What do I do about those ports?

Most hard-core OpenBSD users run -current, which is the continually developing tree of the OS and which is supposed to be pretty stable in its own right. From what I understand of -current, it is relatively easy to update the entire tree, even if quite a bit of time is required for compiling everything.

But I'm running -release. I should be running -stable, which is -release (in this case 4.4) plus patches. But I've never taken the time to figure out how to patch OpenBSD. I really should. But I'm Linuxishly lazy about it. I could barely keep a Slackware system updated with update-pkg. I was always falling behind and welcomed slapt-get and its apt-get-like ability to automate the process.

I don't have that many ports running: Opera and its Flash plugin are really just Linux binaries, as is the Adobe Reader. And I'm in the middle of installing Java, which appears to be the big daddy of OpenBSD ports. I've already downloaded a bunch of binary and source files from a bunch of different places, as directed by the output from the make install of the java port. Tomorrow if I get my act together, I'll start the make install again and see if it'll compile by evening.

So how do I take my ports from 4.4 to 4.5? Do I delete them completely and start anew? I'll have to download a new ports tree, so perhaps the process is somewhat taken care of during the package upgrade since an OpenBSD port's purpose is to fetch, compile if necessary and otherwise prepare a binary package that's installed in the same manner as is a precompiled package on the system.

Another school of thought on upgrading OpenBSD — and more than a few Linuxes as well — is not to upgrade but to reinstall. After backing up /home and /etc, of course, completely reinstall the OS, creating new partitions for everything but /home (and /etc if you're so inclined; merging /etc is part of the "traditional" OpenBSD upgrade process, but if your /etc isn't heavily modified, a complete reinstall of it as well might not be a tragedy. Or it could be ... I'm not enough of an expert at present to say one way or the other).

A reinstall of everything, including /usr, where all the apps live, tends to really clean things up, and it's fairly easy to reinstall one-, two- or three-dozen binary packages, providing you remember exactly what they are. Run pkg_info and save the output — that way you'll have a list of everything you've added, both precompiled binary packages and packages made by the ports system.

I still love running OpenBSD, but I'm thinking pretty hard about how much easier this would all be if I were running Debian, Ubuntu or even FreeBSD, which I have a feeling has some crafty ways of dealing with package and port updates.

Clearly much of this has to do with gaps in my own knowledge, and running OpenBSD is, if anything, a learning experience, so I imagine that learning will continue.

Still, there's the matter of having an up-to-date system that works. To borrow and butcher Ford's moldy slogan, quality (and being as fully patched as possible) is job No. 1.