Re: [exim] SMTPS connection errors with Apple Mac Mail

Top Page
Delete this message
Reply to this message
Author: Viktor Dukhovni
Date:  
To: exim-users
New-Topics: [...]
Subject: Re: [exim] SMTPS connection errors with Apple Mac Mail
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.