Speaking on Deep Background, the Press Secretary whispered:
We see that even when we offer POP with SSL and SMTP AUTH with SSL, few customers wind up using it. That there are continuing problems with the commercial certificate infrastructure doesn't help matters.
Examples of the problems:
1. Eudora contains root certificates only for Verisign and Thawte, and uses its own root certificate store, whereas Microsoft client tools (for all their other weaknesses) include a much broader array of root certificates. If you want to buy certs from someone other than Verisign (since they own Thawte) you have to talk users through integrating other root certs (or your cert) into their copies of Eudora. Or just use a private CA and talk your customers through importing the root cert from your private CA.
While the approval process for other certs in Eudora is obscure, it at least works. I ran into a brick wall trying to get Infernal Exploder for the Mac to accept same; the Windows version was not a problem.
2. SSL incompatabilities: Eudora changed their method of negotiation with Eudora 5.2 and later. The result is an inability to negotiate TLS with Sendmail/Openssl. A configuration parameter in Eudora gets it to go back to the "old way" in their code, which works fine. But now we're talking about another case of talking an end user through a configuration. Might be OK for a corporate setting, but it gets pretty problematic for the ISP.
Note Eudora 6.0 has a public configuration setting for the flavor of SSL.[1] Yes, it should be automagic but "the nice thing about standards in this industry..." applies lots of places...
We've clearly got the mechanisms to allow encryption on the most important of the protocols. However the infrastructure and compatability issues make them more difficult to employ than should be the case.
That these problems show up at networking conferences (IETF, NANOG, etc.), though, really points to a larger problem. If network research, engineering and operations folks can't manage to get encryption deployed for themselves, how likely is it that end customers will use them?
WhatHeSaid. We really need to do a better job of begging/cajoling/requiring encryption. I know one ISP that requires POP/SMTP be on SSL unless you're on their dialup, and I've heard Worldnet does too. [true?] The rest? [1] At least in the Mac version I can lay hands on.. -- A host is a host from coast to coast.................wb8foz@nrk.com & no one will talk to a host that's close........[v].(301) 56-LINUX Unless the host (that isn't close).........................pob 1433 is busy, hung or dead....................................20915-1433