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Shell tips
Theo De Raadt committed a new version of sysupgrade, adding the ability to jump from an old OpenBSD version (down to 5.5 I think) to the latest release available. While this upgrade path is not really supported, it is now possible. The script will download signify keys of the new release, signed by the keys of your current release, this assures a continuity in the chain of trust
You can download the new version from cvsweb and save it locally. Just make it executable and you can run it to jump to a latest release.
Be careful, there is no guarantee the upgrade path will work 100%, although it should work most of the time :)