Socket Error on Outgoing with new SM Installation (2012 R2)
Question asked by CCWH - April 6, 2015 at 5:49 AM
I have just installed SM13 onto a new 2012 R2 box.  I have done this a good few times now and always very simple.  However with this box for some reason any outgoing email tests just sit on the spool.  The log shows this:
[2015.04.06] 13:33:38 [54006] Initiating connection to
[2015.04.06] 13:33:38 [54006] Connecting to (Id: 9)
[2015.04.06] 13:33:38 [54006] Binding to local IP (Id: 9)
[2015.04.06] 13:33:59 [54006] Exception connecting to (Id: 9)
[2015.04.06] 13:33:59 [54006] 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
[2015.04.06]    at System.Net.Sockets.Socket.DoConnect(EndPoint endPointSnapshot, SocketAddress socketAddress)
[2015.04.06]    at System.Net.Sockets.Socket.Connect(EndPoint remoteEP)
[2015.04.06]    at RelayServer.Clients.SMTP.ClientConnectionSync.Connect(Int32 connectionId)
[2015.04.06] 13:33:59 [54006] Connection to failed (Id: 9)
Outgoing IP is -
It looks like some kind of IP Binding issue.  Has anyone seen this before and if so what is the issue?
Just to add, I get the issue no matter what email server I send to...even one of our other SM servers on a different network.  I also added a different test domain name to the SM but that resulted in the same error.

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Do you have Internet access?
Are ports 25, 110, 80, 443, and any other bound ports open on your firewall(s)?
Are all of your PORTS bound to the proper IP address(es)?
If you moved to a new box, and a new operating system, do you have new IP ADDRESSES?  If so, did you change them in all of your BINDINGS, DOMAINS and SMTP settings?
Are your DOMAINS bound to a valid IP address?
Is your OUTBOUND SMTP properly configured to use either the DOMAIN's IP ADDRESS or a selected IP address?
If you are not using IPV6, did you DISABLE it - EVERYWHERE?
This is just a start, there are many other places to look.
Bruce Barnes
ChicagoNetTech Inc

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Thanks Bruce. I eventually got to the bottom of this one. The new hardware was placed in a new datacentre and we were not informed that ALL outgoing port 25 traffic was blocked and only a relay would be offered at extra cost per month.... Needless to say we have now moved the hardware elsewhere! Hopefully tomorrow morning I can start work on the new server.

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