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I'd like to see a free CA for S/MIME certificates once again.

Since more than a year or two, all the free S/MIME certificates that you can get these days have issues:

- some of them a valid less than one year which is a huge hassle for S/MIME as opposed to HTTPS because you need to keep all your old certificates around

- some of them will not let you use your own private key (I wish i was kidding)

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I don't know S/MIME, why do you need to keep your old certificates?

From my understanding S/MIME is pretty much enterprise PGP, so if you don't have your old certificates you can't access old emails that were encrypted using them

i've always reencrypted when getting a new cert. not sure if thats an antipattern though. i just didn't want to be bothered by which cert encrypted what data

Encryption is performed with private key, not with certificate. If you can issue new certificate for the same private key, it should be able to decrypt old stuff.

Rotating keys might be a good security practice, though. But not necessary.

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