On Feb 27, 2007, at 5:42 PM, Stephen Warren wrote:

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> Amitai Schlair wrote:
>> On Feb 27, 2007, at 5:06 PM, Jason R. Mastaler wrote:
>>
>>> Amitai Schlair <[EMAIL PROTECTED]> writes:
>>>
>>>>> With Apple Mail.app (which only does TLS):
>>>> Hm? I've been using it with SSL for years...
>>> Are you sure? The Mail.app config screen says SSL, but it's actually
>>> doing STARTTLS. If you run tmda-ofmipd with the '-d' option and look
>>> at the trace of the session it shows that.
>>
>> Until recently I had stunnel listening only on port 465 and not doing
>> anything SMTP-specific, and Mail.app sent mail through tmda-ofmipd
>> that way just fine. Maybe Mail.app falls back from one to the other
>> in a way that the UI only needs to expose "encrypt SMTP (y/n)?".
>
> Did your stunnel.conf contain this line?
>
> protocol = smtp
>
> That makes it do STARTTLS, otherwise it does "plain" SSL (if I recall
> correctly) I don't believe stunnel interprets the port number in any
> way, so it doesn't automatically know "the correct" mode to operate in
> simply because it's listening on port 465.

Until recently, no. That's what I meant by "not doing anything SMTP- 
specific." The whole of the config file was:

-----

cert = /etc/openssl/certs/schmonz-cert3.pem
key = /etc/openssl/private/schmonz-cert3.key
debug = mail.info
setuid = tofmipd
setgid = tofmipd
pid =

[smtps]
accept = smtps
connect = localhost:tofmipd

-----

So it can only have been a dumb SSL tunnel, ergo Mail.app must be  
capable of speaking SMTPS. (This message is sent that way, too. :-)
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