Since Gmail allegedly supports S/MIME now, and Mac and iOS Mail have for ages, I thought I'd buy a certificate and try using it to see how people reacted.
Got through the sales process, and it turned out the CA hadn't updated its site in years and it only worked with either (a) Internet Explorer or (b) Firefox 68 or earlier, neither of which will run on my Mac for obvious reasons.
So, refund for that, and does anyone know of a CA that sells S/MIME certificates cheaply, that doesn't require that you own the entire domain, and that has a web site that works?
@mathew FWIW, my short experience using S/MIME (some time ago now) was that nobody knew or cared what it was, and I would get the occasional reply expressing concern that I might have a virus, because the signature showed up for the recipient as an attachment they weren't expecting with an unfamiliar file extension.
@daisy @mathew I have basically the same experience using OpenPGP long ago (people didn't think it was a virus, but the signatures did prevent some clients from properly displaying my emails). S/MIME seems to work okay in large organizations that support it, but even then my experience is that it's pretty messy if you try to talk to someone from another organization; there's often no way to retrieve someone's certs other than asking the intended recipient and often you don't have a trusted mechanism to get the public root cert for the other organization, undermining the usefulness of signatures for authentication.
