I run my own email server (Mailenable) and have to use an alternate SMTP port to get around a firewall at work. I also use ASSP (spam filter as a middle-man which greatly reduces my spam issues. I’m using SSL/TLS authentication and this setup has worked fine for years using Mozilla Thunderbird, and K-9 for Android so I’m confident it’s not a system/architecture issue. I’ve recently decided to try eM Client based on a friend’s recommendation, and it’s not going so well.
In Thunderbird, the config is Connection Security=SSL/TLS & Authentication Method=Normal Password
I’ve tried all 4 configuration options in SMTP setup, and none will connect to send emails. After looking at the server logs, it appears to *try* and is pretty successful, but ultimately the app thinks it fails. I can see that the connection is made and some dialog between server & eM Client. See the server logs shown below.
Here’s my setup for clarity (again, working fine with other email apps)
eM Client --port 465–> LAN Router NAT --port 466–> ASSP SPAM server --port 465–> MailEnable SMTP Server
Here are both the eM client logs for the associated connection, and the SMTP server logs I have (since I own the SMTP box)
SMTP debug output from eM Client
SMTP S: 220 mydomain.com ESMTP MailEnable Service, Version: 0-6.70- ready at 01/04/13 16:25:32
SMTP C: EHLO [111.111.111.111]
SMTP S: 250-mydomain.com [127.0.0.1], this server offers 5 extensions
SMTP S: 250-SIZE 30720000
SMTP S: 250-HELP
SMTP S: 250-AUTH=LOGIN
SMTP S: 250 NOOP
[blank line here since HTML won't show it]
ASSP mail log
Jan-04-13 16:25:38 [SSL-in] 111.111.111.111 MTA offered STARTTLS - converting to SSL;
ex_log
2013-01-04 16:25:38 127.0.0.1 SMTP-IN 127.0.0.1 1016 EHLO EHLO+ASSP.nospam 250-mydomain.com+[127.0.0.1],+this+server+offers+5+extensions TERASERVER2 152 18
2013-01-04 16:25:38 127.0.0.1 SMTP-IN 127.0.0.1 1016 STARTTLS STARTTLS TERASERVER2 24 10
2013-01-04 16:25:38 127.0.0.1 SMTP-IN 127.0.0.1 1016 EHLO EHLO+ASSP.nospam 250-mydomain.com+[127.0.0.1],+this+server+offers+4+extensions TERASERVER2 138 18
SMTP Debug
01/04/13 16:25:38 [1016] Initializing SSL Conversation
01/04/13 16:26:09 SSL recv failed: 10060 on socket [1016]
01/04/13 16:26:09 ME-I0070: (recv) socket [1016] was gracefully closed during [EHLO] command by the remote client 127.0.0.1.
01/04/13 16:26:09 ME-I0074: [1016] (Debug) End of conversation
SMTP Server Activity Log
01/04/13 16:25:38 SMTP-IN 8C7AAF5A671D470987BD7F37D96134BD.MAI 1016 127.0.0.1 EHLO EHLO ASSP.nospam 250-mydomain.com [127.0.0.1], this server offers 5 extensions 152 18
01/04/13 16:25:38 SMTP-IN 8C7AAF5A671D470987BD7F37D96134BD.MAI 1016 127.0.0.1 STARTTLS 24 10
01/04/13 16:25:38 SMTP-IN 8C7AAF5A671D470987BD7F37D96134BD.MAI 1016 127.0.0.1 STARTTLS STARTTLS 24 10
01/04/13 16:25:38 SMTP-IN 8C7AAF5A671D470987BD7F37D96134BD.MAI 1016 127.0.0.1 EHLO EHLO ASSP.nospam 250-mydomain.com [127.0.0.1], this server offers 4 extensions 138 18