Hello, I'm trying to configure exim-4.80 with SMTPS and experiencing connection problems from an Apple Mac Mail client (mac os x 10.9.5, mac mail 7.3).
Perhaps someone has dealt with similar issues and can advise? My setup is: exim-4.80, self-signed certificates, with the following options: tls_on_connect_ports = 465 daemon_smtp_ports = 25 : 465 Sadly I can't use port 587/25 with STARTTLS - I need to use the TLS-on-connection option. I've tested the following which all work fine: openssl s_client -connect myserver:465 swaks --tls-on-connect --auth --server myserver thunderbird 31.5 on ubuntu iPhone mail iOS 7 But the apple mail client does not work. In the exim mainlog, I get: TLS error on connection from [[IP]] (gnutls_handshake): A TLS packet with unexpected length was received. I tried compiling from source with OpenSSL, and get this: TLS error on connection from [[IP]] (SSL_accept): error:00000000:lib(0):func(0):reason(0) TLS client disconnected cleanly (rejected our certificate?) The certificate is self-signed, but I've installed it in the Mac manually and marked it as "always trust". 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. Thanks! - Assaf -- ## List details at https://lists.exim.org/mailman/listinfo/exim-users ## Exim details at http://www.exim.org/ ## Please use the Wiki with this list - http://wiki.exim.org/
