Hey!
0x800CCC0E IXP_E_FAILED_TO_CONNECT Cannot connect to server Pretty helpful error message after all... ;-)
Well, _did_ you've verified that the connection is started at all? Yup. As written in my first mail, the client tears down the connection after the ssl key exchange with a FIN,ACK.
I mean: http://support.microsoft.com/kb/302339/EN-US
"If you are connected to the Internet through MSN, the Microsoft Network, and you attempt to send messages by using an account other (...) (SSL): No, Socket Error: 10051, Error Number: 0x800CCC0E The windows machine is a vm on my machine. No antivirus, no nothing inbetween -- just win8.1 (at the latest patch level) and outlook.
Did you checked the connection with wireshark / tcpdump on the server side? What side sents the last packet, does one side terminates the connection, ... ? Yes. And as I said already: the connection with s_server works from the very same setup.
Here is a log extract from just right now with 'verbose_ssl': Jun 26 13:56:36 mail dovecot: imap-login: Debug: SSL: elliptic curve secp384r1 will be used for ECDH and ECDHE key exchanges Jun 26 13:56:36 mail dovecot: imap-login: Debug: SSL: where=0x10, ret=1: before/accept initialization [10.10.10.20] Jun 26 13:56:36 mail dovecot: imap-login: Debug: SSL: where=0x2001, ret=1: SSLv3 read client hello A [10.10.10.20] Jun 26 13:56:36 mail dovecot: imap-login: Debug: SSL: where=0x2001, ret=1: SSLv3 write server hello A [10.10.10.20] Jun 26 13:56:36 mail dovecot: imap-login: Debug: SSL: where=0x2001, ret=1: SSLv3 write certificate A [10.10.10.20] Jun 26 13:56:36 mail dovecot: imap-login: Debug: SSL: where=0x2001, ret=1: SSLv3 write key exchange A [10.10.10.20] Jun 26 13:56:36 mail dovecot: imap-login: Debug: SSL: where=0x2001, ret=1: SSLv3 write server done A [10.10.10.20] Jun 26 13:56:36 mail dovecot: imap-login: Debug: SSL: where=0x2001, ret=1: SSLv3 flush data [10.10.10.20] Jun 26 13:56:36 mail dovecot: imap-login: Debug: SSL: where=0x2002, ret=-1: SSLv3 read client certificate A [10.10.10.20] Jun 26 13:56:36 mail dovecot: imap-login: Warning: SSL failed: where=0x2002: SSLv3 read client certificate A [10.10.10.20] Jun 26 13:56:36 mail dovecot: imap-login: Disconnected (no auth attempts in 0 secs): user=<>, rip=10.10.10.20, lip=10.10.10.10, TLS handshaking: Disconnected So, yes, I guess outlook talks to dovecot...
-- Adi