I've been using OpenBSD since way back at release 2.3 in 1998, so I've gone through upgrades that took a fair amount of work due to incompatible changes, like the switch from ipf to pf for host firewalling or the change to ELF binaries. The upgrade from 5.7 to 5.8 was a pretty smooth and easy one, for the most part. The two most painful changes for me were the replacement of sudo with doas and the dropping of support in the rc.conf for the pf_rules variable. While sudo is still available as a package, I like the idea of reducing attack surface with a simpler program, so I made the switch. The two things I miss most about sudo are the ability to authenticate for a period of time and the ability to have a single config file across a whole set of servers. The former I'm just living with, the latter I've adjusted to by having a single config file that has lines commented out depending on which server it's on. I did have one moment of concern about the quality of doas when it incorrectly reported the line number on which I had a syntax error in the config file--fortunately, this was just a failure to increment the line count on continuation lines (ending with a "\") which is fixed in the -current release.
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