OpenBSD: Upgrade anxiety
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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. 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.
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