Socket Error on Outgoing with new SM Installation (2012 R2)

Question asked by CCWH - 4/6/2015 at 5:49 AM

Answered

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 65.55.37.88
[2015.04.06] 13:33:38 [54006] Connecting to 65.55.37.88:25 (Id: 9)
[2015.04.06] 13:33:38 [54006] Binding to local IP 109.200.13.100:0 (Id: 9)
[2015.04.06] 13:33:59 [54006] Exception connecting to 65.55.37.88 (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 65.55.37.88:25
[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 65.55.37.88 failed (Id: 9)

Outgoing IP is - 109.200.13.100

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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Bruce Barnes Replied

4/6/2015 at 12:53 PM

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 brucecnt@comcast.net Phonr: (773) 491-9019 Phone: (224) 444-0169 E-Mail and DNS Security Specialist Network Security Specialist Customer Service Portal: https://portal.chicagonettech.com Website: https://www.ChicagoNetTech.com Security Blog: http://networkbastion.blogspot.com/ Web and E-Mail Hosting, E-Mail Security and Consulting

CCWH Replied

4/6/2015 at 1:48 PM

Marked As Answer

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.

Matt Petty Replied

4/6/2015 at 2:42 PM

Employee Post

Ick, well hopefully you found a better place for your hardware, good luck.

Matt Petty Senior Software Developer SmarterTools Inc. www.smartertools.com

Bruce Barnes Replied

4/6/2015 at 3:17 PM

DAMN! Who was the hosting company? We all need to make certain we never use them.

CCWH Replied

4/6/2015 at 10:49 PM

A company called Redstation in the UK. They are owned by Iomart which is huge. The reasoning they gave was to stop email abuse on their leased IP addresses. I was disgusted, especially as within our consultation with them prior to our agreement they confirmed there was no filtering! Wasted a bank holiday weekend setting up a server for nothing! The crazy thing is after I found out it was only then that they said I could pay to bypass their blocks! It was like blackmail... A hidden cost to an email server provider.

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