I don't understand what you mean by "certs breaking".
You probably need to let go of the ideal that decades-old software should be able to be connected to a public network.
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Yeah it's a bit silly, but I like to build software to last without forced expiration dates (only end of support).
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It's certainly a mistake if a sysadmin connects an old OS of mine to the internet. But people trying out historical stuff in a VM?
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A part of me likes the idea of a decades old system booting, then installing updates for a few hours, and now it's the latest system.
End of conversation
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