I've tested HTC Mail with the gmail imap server and from that I think I've found the problem. HTC Mail does support SSL but my mail server uses self-signed certificates and the version of HTC Mail on the 2.1 ROMS doesn't accept these (the orange stock HTC prompts you to accept unsigned certificates)
I'll have to dig-out the CA file from the server, convert it to pkcs12 and add it to the phone, that should fix it.
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