On Fri, Mar 13, 2015 at 09:40:26PM -0400, Assaf Gordon wrote:

> But the apple mail client does not work.

That's likely a misconfiguration of the apple Mail client.

    Preferences->
        Accounts->
            Outgoing Mail Server (SMTP)-> (Menu item)
                Edit SMTP Server list -> ("Advanced" view)
                    * Use custom port (enter 465)
                    * Use Secure Sockets Layer (SSL) (check)

                    Configure the correct username and password!

Test with

        Window->
            Connection Doctor
                

> In the exim mainlog, I get:
>   TLS error on connection from [[IP]] (gnutls_handshake): A TLS packet with 
> unexpected length was received.

This sure looks like a client-side issue.  Or perhaps GnuTLS is
misreporting the client disconnecting as "unexpected length".

> I also looked with wireshark (on the mac), and the connection starts on
> port 465 with TLSv1 (sending "Client hello" and receiving "Server Hello")
> - so I would think the configuration on the Mac Mail is correct (i.e. it
> doesn't start in plain text and tries STARTTLS).
> But then - it just stops and doesn't continue.
> 
> Any advice or suggestions on how to even start debugging it will be 
> appreciated.

MacOS/X will generally prompt to accept self-signed certs, which
end up on the keychain as trusted for the site in question (admin
password required).

-- 
        Viktor.

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