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SMTP relay from copy machine to office365 slow

Posted on 2013-11-13
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Last Modified: 2013-11-15
I have had one heck of a time trying to get SMTP relay to work from a copier to office365 exchange account, but I got it working.  A quick synopsis...

We are an organization planning to migrate from a local Exchange 2003 box to an office365 hosted solution, and then decommission the exchange server.  One of the challenges presented in this regard was the fact that some of our corporate copiers did not support the required TLS encryption to connect to O365.  The answer to this problem I'm told is to set up an SMTP relay on one of our other server boxes.  I followed KB article for microsoft (http://support.microsoft.com/kb/2600912), which left out some important details, but I DID successfully get Relay to work.  I am able to send messages from the copier.  

The problem is, the relay is SLOOOW.  Messages sit in the queue for 5-30 minutes before finally getting delivered. (C:\Inetpub\mailroot\Queue)  

What do I need to do to get these messages to deliver faster? any ideas?
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Question by:Trenton Knew
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by:strivoli
ID: 39647889
Is the SMTP relay pointing to the correct DNS servers?
Does the Windows Application Log (run eventvwr) report any related Warnings/Errors?
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Aaron Tomosky earned 1000 total points
ID: 39647906
For a local smtp relay for exactly the same purpose, I use hmail server. It's tiny fast and free.
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by:Trenton Knew
ID: 39648601
I don't know if this helps, but I set up an identical relay on a 2008 install on a VM and there is immediate delivery from that box.  I only have trouble when I relay through my 2003 box that is also running a full IIS web and SQL server.  I suppose it could also be the security software running on that box.  There might be too many variables at play to really get a good and clear answer on this here.
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by:Aaron Tomosky
ID: 39648626
Sounds like that box is the problem then. Do hmail or do your way. Need help with anything else? Hmail is super simple but let me know if you need help.
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by:Trenton Knew
ID: 39651499
I suppose there may be some odd configuration on the firewall to prevent the web server box from becoming a spam jump off point.  I haven't been here long enough to fully understand the security configuration in place yet.  For now, I might set up an Ubuntu server box for the SMTP relay.
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