On Thu, 1 May 2008, Ken Keating wrote:
How did you do this?  Did you change IMAPSSLPORT in imap4r1.c from 993
to 994 (the most straightforward way)?  Or did you use some other
means?  If so, what?
We didn't change IMAPSSLPORT.  We're running Solaris 10 and controlling
this through inetd:

Hmm. I still don't understand how imapd knows on your system that it is to run in SSL mode on port 994 as opposed to plaintext mode. It chooses SSL if (and only if):
 . it is on the imaps port (port 993)
or
 . the port is not the imap port (port 143) or imaps port (port 993) AND
   the name of its binary starts with "s"

I guess that you must be doing the latter, since your message definitely describes an imapd in SSL mode. OK by me... ;-)

To test for [2], run a packet sniffer and try a connection.  If both
sessions are quiet after connecting, that suggests [2], since a
plaintext IMAP client expects to be spoken to before it speaks, and in
SSL the client starts speaking first.
I think this describes what I'm seeing, but I'm going to run it by one
of my much more experienced colleagues to see if his interpretation is
the same.

Another test you can do is to get a non-SSL server running on port 994 and seeing if it works. If so, that would be pretty strong indication that the client is not in SSL mode.

Finally, turn on debugging telemetry in Mail.app.  I don't know how to
do that, but I know that it can be done.  See what the log there says.
If you see any IMAP protocol negotiations, either figure them out
yourself or pass it on to me and I'll tell you what it was doing.
I'm still trying to turn on any useful debugging in Mail.app.

I've asked our local Apple expert to get in touch with you and tell you have to get debugging telemetry with Mail.app.

Simon indicated in another response that there may be a problem if we use a self-signed certificate. We may have a self-signed certificate in our chain, but we definitely have an externally-signed certificate as well.

Bizarre if that is the cause.

I'm going to see if I can find an appropriate Mac users group and ask if anyone there is running imapd 2007a against Mail.app 2.1.3 on OS X 10.4.

Good luck!  Please let me know what you find.

-- Mark --

http://staff.washington.edu/mrc
Science does not emerge from voting, party politics, or public debate.
Si vis pacem, para bellum.
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