Exchange 2013 Mail Flow / Server Issues

We currently have Exchange 2013 sitting on a Server 2012 VM at a site of ours. The mail is currently running through a smart host for Spam Filtering. There are multiple distribution groups under multiple domains configured and set as 'reply to' so the users can change their From address. Whats happening it they have people theyre sending to report that mail is not getting through to them and vice versa. This isnt constant, and happens randomly throughout the week. They arent receiving any NDRs and it doesnt appear that things are getting stuck in the Queue or in the receiving parties spam filter. Also at times it seems that mailflow is extremely slow, sometimes taking up to 10-15 minutes for mail to go through. After a few days, they will actually lose connection to Exchange all together which requires a server reboot to bring the connection back up. If I run Test-MailFlow, I receive *FAILURE*. Basically im looking for a good place to start troubleshooting. I feel that theres issues on both the server side, as well as software.
Any ideas?
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paulrauschAsked:
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piattndCommented:
Run the exchange BPA (best practices analyzer) tool to see if there's a configuration change.  They're pretty good at finding things that will likely slow down your performance.

Additionally, they have a troubleshooting assistant that will check specific things that could cause slow or failed mail delivery.

I know 2010 comes with it installed already.  You should be able to get it from this link:

http://technet.microsoft.com/en-us/exchange/bb288481.aspx
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paulrauschAuthor Commented:
From what I understand, ExBPA isnt yet available for Exchange 2013. Is this correct?
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piattndCommented:
It actually does look like you are correct.  It even looks like the TRA wasn't included (as of yet) for Exchange 2013.

This link demonstrates performing some troubleshooting tests via the powershell cmdlet

http://exchangeserverpro.com/troubleshooting-exchange-server-2013-with-test-cmdlets/

Give the mail flow a try.  I don't know it's full capability to fully replicate the behavior your users are doing, but pay special attention to not only failures, but the message latency.
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Simon Butler (Sembee)ConsultantCommented:
There is a beta of BPA.
http://blogs.technet.com/b/exchange/archive/2013/10/01/beta-of-microsoft-office-365-best-practices-analyzer-for-exchange-server-2013-now-available.aspx

Primary cause of these problems is AV scanning something it shouldn't. If you have AV on the server ensure that it has the correct exclusions.

Simon.
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paulrauschAuthor Commented:
Piattnd/Sembee2,
Thanks for the provided Links. Im actually in the process of pushing out updates and prepping to install CU2. Once complete ill dig deeper into my Diagnostics and see what I come up with.

We dont currently have AV running on the server, but after a deep scan of the VM, over 400 items were discovered. Ive gone ahead and locked down the server, and will be checking functionality tomorrow. I wouldnt doubt this was playing a part in the issues the EU was experiencing.

Ill keep you both updated.
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paulrauschAuthor Commented:
Update:
Ive pushed out CU2 and disabled things like Malware and Content Filtering. I Ran the BPA and the only things that were really flagged were OAB and Backups. I Changed the DNS inside ECP on external and internal to my adapter #2 which uses the Internal DNS Servers. Internal mail is now flowing between boxes within 2-4 seconds. External to Internal is still hit or miss. Sometimes it will run through within about 20-30 seconds, but the majority of the time we're looking at roughly 3-6 minutes, sometimes up to 15minutes.
Any ideas what else I could take a look at?
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Simon Butler (Sembee)ConsultantCommented:
"my adapter #2 which uses the Internal DNS Servers"

Stop right there.
Are you saying this server is dual homed?

Simon.
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paulrauschAuthor Commented:
Yes, Virtualized. I apologize for not mentioning sooner. Ive been coming across some posts where other people are having the same issues with Exchange 2013.  The below article being one of them.

http://social.technet.microsoft.com/Forums/exchange/en-US/fc23776c-bae4-4ca9-ad6d-4f8df880f47c/451-470-temporary-server-error-please-try-again-later-prx2
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Simon Butler (Sembee)ConsultantCommented:
Microsoft haven't recommended dual homing an Exchange server for some time, I actually think it isn't supported except for DAG replication. Why is it dual homed?

Simon.
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paulrauschAuthor Commented:
Wasnt configured by myself. My next step was to actually kill the WAN interface and simply forward the correct ports to see if that had any effect on the performance.
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Simon Butler (Sembee)ConsultantCommented:
That is how it should be configured. Putting Exchange in to any kind of permiter network isn't supported on Exchange 2007 and higher.

Simon.
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paulrauschAuthor Commented:
Alright Then. Im going to give it a shot tomorrow and see where I get.
Thanks for your input, will keep you posted.
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paulrauschAuthor Commented:
Resolved. You get all the points!
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