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Date: Wed, 30 Oct 2013 22:56:08 +0100
From: Andrea Venturoli <ml@netfence.it>
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Subject: [Half OT] Mavericks' Mail and SSL
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Hello.

Has anyone tried connecting OS X 10.9's Mail.app to sendmail with SSL?

Server side all I get is:

> sm-mta[53510]: STARTTLS=server, error: accept failed=0, reason=unknown,
 > SSL_error=5, errno=0, retry=-1, relay=...

Client side, the SMTP server is marked as offline, with no other 
explanation.
Of course it all worked flawlessly until the customer decided to upgrade 
from 10.8...

I couldn't come a to a conlusion myself, but I'm seeing a lot of threads 
about this out on the net; however, no solution is proposed.

My guess is either a bug on the client side (as someone goes on to 
suggest) or some exotic variation of the protocol... perhaps I need some 
OpenSSL tweak? Some specific settings in sendmail's config?

I tried both base's and ports' OpenSSL, but nothing seems to change.

Any hint is appreciated.

  bye & Thanks
	av.