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Old 8th January 2009
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snes-addict snes-addict is offline
Real Name: Ken
BSD gamer
 
Join Date: Oct 2008
Location: Minnesota, USA
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In terms of doing binary upgrades from one release to another, you shouldn't have any problems as long as you upgrade to the release which comes right after yours (e.g. 4.0 -> 4.1, NOT 4.0 -> 4.4).
Quote:
Originally Posted by OpenBSD FAQ
Note: Upgrades are only supported from one release to the release immediately following it. Do not skip releases.
Keeping this in mind, the only thing you should have to worry about is properly merging in the new /etc files with your own installed /etc files.

In your case, having missed several releases, I'd probably just backup all important data and install 4.4-release from scratch; it's the easiest solution.

As per your other question, I cannot really say much about GNU/Linux security updates because I don't follow any distros (I wouldn't be surprised, however, if OpenBSD is still more secure).
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