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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.

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