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I think the issue the upper poster is referring to are things like when chrome deprecated ancient certificate features, which enterprise-solutions still happen to use by default 15 years after they were deprecated.

(One such issue were certificates with a common name and no subject alt name.)

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Yes, the common name and the no SAN was one of those problems. It didn't help that 90% of all tutorials to do a self signed CA only set a CN, and sometimes you had dependent internal systems. How this appears to people who end up servicing tickets are just 'Chrome doesn't work anymore' and having to answer many people that 'Chrome won't work any more until a larger business process resolves, and there's nothing we can do about it' really sucks. Also to an end user who might be a nontechnical administrator of a enterprise application there was no indication that it was going to become a problem, they just show up to work one day and they can't work.

That issue bit me in the ass, but my biggest complaint about it was the horrible error message that Chrome gave making it impossible to figure out what the problem was.

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