Stewart Dean wrote:
It looks like Mail.app treats "non-standard" ports differently.  On the
standard port (993), the "SSL" option seems to do pure SSL; but with another port specified, it does clean-plus-starttls (and hence fails horribly, because
it's talking to a pure SSl service)
Is there anything I can do to get MacMail to behave correctly? Or will it clear up when I shut down UWIMAP and give Dovecot the default ports. A Bronx cheer for Mac Mail........

It's possible it *might* clear up when you move to the standard ports; the server advertises STARTTLS capability (well, at least my Dovecot build does :) ). so it's possible that the Mail app is sniffing the server CAPABILITY flags, seeing a non-default port and trying to do something smart. I found this blurb:

"Apple’s Mail application has checkboxes to enable TLS for incoming Internet Message Access Protocol (IMAP) or outgoing SMTP connections. STARTTLS or direct TLS is used automatically, depending on the target port." (http://sial.org/howto/openssl/tls-name/)

If you have tcpdump (or similar) on one of your OS X boxen, fire it up and trap the packets between the two servers and check out the net traffic and what ports it's trying to use. That'd be where I start...

Also, check out this blog post:
http://blog.scottlowe.org/2005/07/02/starttls-and-imap-in-mailapp/

"So, it appears that Mail.app does indeed support STARTTLS for IMAP, but only if you set the port number back to 143 after checking the “Use SSL” checkbox."

-te

--
Troy Engel | Systems Engineer
Fluid, Inc | http://www.fluid.com

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