I've been experiencing this issue too, over the last couple of weeks.
Interestingly, only one of my two Macs is affected, and neither of the
family iPhones, so I'm not sure it's definitely an exim bug - I think
it may be a problem with Mail.app.
My suspicion fell on the certificate management in the Keychain. I
quit Mail, opened the Keychain Access application, and deleted
anything I could find in the Mac account's keychain relating to my
Debian mail server (its self-signed certificate, and any saved
passwords). I then tried Mail again, and *touch wood* I haven't seen
any recurrence of the problem, but it's been less than 24 hours, and
my wife -- who was the main affected user -- hasn't tried using her
account much yet, so watch this space.
Another aspect of the issue, which you may wish to confirm in your
case, is that Mail claims that the SMTP server is offline, even when
it isn't. This is still the case for me, even though the account can
successfully send mail through my exim SMTP server. So whatever Mail
is doing to test the availability of the SMTP server clearly isn't
quite working properly, although whether that's the fault of Mail.app
or exim is unknown. I suspect Mail, because Thunderbird on the Mac
has no problem using my exim setup (you might want to confirm this
yourself also)
For completeness of information, the client is currently running on
Mac OS X 10.6.1, but I'm fairly certain Mac OS X Server 10.5.8, which
I was running previously, was also affected. The Mac that works fine
is running Mac OS X 10.5.8 client edition.
Tim
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