Update 2017-04-17: Minor updates to adjust to the post-6.1 world, such as no more CDs. Thanks to Marc Espie for (as always) valuable input.
Update 2018-06-12: Modern
man.openbsd.org links are much simpler now than when this was originally written, links updated. Also small tweaks to make the text reflect the user visible changes to the upgrade program.
Update 2019-04-26 + 2024-09-01: Now that you've read this piece to the end and have probably gone through more than a few manual steps, you will probably be pleased to hear that the process is now about to become significantly simpler in almost all cases.
Only hours after the news of the
OpenBSD 6.5 release hit, the new
sysupgrade(8) command was added to OpenBSD-current, and so will most likely be part of the OpenBSD 6.6 release, expected in about six months. In its present form,
sysupgrade(8) only performs the base system upgrade, so the
pkg_add(8) parts mentioned in this piece will still be needed as a separate step. Further details will be available as development proceeds, but now you know about at least one thing to look forward to in
OpenBSD 7.6 (due some time in late October to early November of 2024, with the release page starting to emerge some weeks ahead of that date.