I have migrated my SmarterMail to a new server. Everything went smoothly to get back up and running where I could log into the web interface and see my domains. Everything seems to be running fine in the web admin. I can log into various use mailboxes and see mail, etc. I did have to go into settings and change my ip and hostnames. I'm not sure if I got them updated everywhere, but I think I have.

 

I can check email (pop) from my Outlook client now just fine. My problem is sending email. I cannot send from the web interface or from Outlook.

 

All sent messages are seen in the All Messages spool with a status of Waiting to Deliver. I isolated one in the delivery log and this is what I'm seeing.

 

[2017.01.03] 06:23:17 [13017] Delivery started for trent [at] trentgrandey.com at 6:23:17 AM
[2017.01.03] 06:23:23 [13017] Skipping spam checks: No local recipients
[2017.01.03] 06:23:26 [13017] Sending remote mail for trent [at] trentgrandey.com
[2017.01.03] 06:23:26 [13017] Spam check results: [_INTERNALSPAMASSASSIN: 7:7]
[2017.01.03] 06:23:26 [13017] Initiating connection to 199.168.255.196
[2017.01.03] 06:23:26 [13017] Connecting to 199.168.255.196:25 (Id: 1)
[2017.01.03] 06:23:26 [13017] Binding to local IP 216.198.212.38:0 (Id: 1)
[2017.01.03] 06:23:47 [13017] Exception connecting to 199.168.255.196 (Id: 1)
[2017.01.03] 06:23:47 [13017] System.Net.Sockets.SocketException (0x80004005): A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 199.168.255.196:25
[2017.01.03]    at System.Net.Sockets.Socket.DoConnect(EndPoint endPointSnapshot, SocketAddress socketAddress)
[2017.01.03]    at System.Net.Sockets.Socket.Connect(EndPoint remoteEP)
[2017.01.03]    at RelayServer.Clients.SMTP.ClientConnectionSync.Connect(Int32 connectionId)
[2017.01.03] 06:23:47 [13017] Binding to local ip '216.198.212.38' failed.  Switched binding to primary local ip.
[2017.01.03] 06:23:47 [13017] Connecting to 199.168.255.196:25 (Id: 2)
[2017.01.03] 06:24:08 [13017] Exception connecting to 199.168.255.196 (Id: 2)
[2017.01.03] 06:24:08 [13017] System.Net.Sockets.SocketException (0x80004005): A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 199.168.255.196:25
[2017.01.03]    at System.Net.Sockets.Socket.DoConnect(EndPoint endPointSnapshot, SocketAddress socketAddress)
[2017.01.03]    at System.Net.Sockets.Socket.Connect(EndPoint remoteEP)
[2017.01.03]    at RelayServer.Clients.SMTP.ClientConnectionSync.Connect(Int32 connectionId)
[2017.01.03] 06:24:08 [13017] Connection to 199.168.255.196 failed (Id: 2)

 

I am sending an email from trent [at] trentgrandey.com to trentg [at] ppai.org. trentgrandey.com is a domain on my SmarterMail server.

 

199.168.255.196 happens to be the ip address of the @ A record for ppai.org, the domain I am sending to in the above log. 216.198.212.38 is the ip address of my server that is running SmarterMail.

 

As I was writing this, I realized that the 199.168.255.196 ip address is NOT the mail server for ppai.org. That is odd an most assuredly why it cannot connect. Is there some setting in SmarterMail that would cause it to not query for the correct address? The MX records on the ppai.org domain are outmail.ppa.org which resolves to 12.203.50.113.

 

I have to believe I am missing some setting, but I can't figure out which one. I'm running SmarterMail professional 15.4.

 

Thank for any help and let me know if you need any more information!

 

Trent