Delayed email delivery Exchange 2007 SP1 / Barracuda / Server 2008

I have recently set up an exchange environment for a client.  They are a small company with less than 50 user accounts.  The server has been running fine for over two weeks, however users are now receiving incoming emails hours after they have been sent.

The configuration I have setup is mail comes in through an ASA5505 with Static NAT directing the traffic to a Barracuda 300 Spam and Virus filter.  The Barracuda does it thing and then forwards the mail to the Exchange server.  In the message log of the Barracuda it shows that the email has been received and "allowed", but it doesn't show up in the users mailbox for a long time.

Any ideas?  Thank you.
jsalisb4Asked:
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Rick FeeMessaging Engineer - Disaster Recovery EngineerCommented:
Can you take a look at Message Tracking on Exchange to see when the server actually received it?   Also for the Cisco did you turn off the SMTP fixup, this might not have anything to do with it...just a good pratice:

conf t
no fixup protocol smtp 25

So back to the Barracuda/Exchange...look at both recieve times and see if they are off at all....let me know what you find.
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jsalisb4Author Commented:
OK.  The times are pretty close.  I had already check to make sure that SMTP inspection was off.  What is that in the message tracking log there are events for "SMTP RECEIVE" but it shows that the client IP address is the IP Address of one of my servers ILO's???  Do you know what this is?  Thanks.
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jsalisb4Author Commented:
Wow.  I don't know how I let that post through with such bad grammar! Sorry about that.  I also forgot to attach the screen shot of the tracking log that I mentioned.
exchangelog.png
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jsalisb4Author Commented:
Uggg... Now I am feeling really stupid.  I hadn't expanded the column all the way.  It is the correct IP address of the mail server.  Client is the mail server, and server is the IP address of the Barracuda.
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Rick FeeMessaging Engineer - Disaster Recovery EngineerCommented:
Ok so in the message tracking log...the timestamp set for Receive/Storedriver is when Exchange has accepted the email.   It should then be available...but you indicated that it takes hours.    So is this via the Outlook client?     As a test can you use OWA to see if the email is there and not updated with the Outlook client?    In addition is your time zones setup on the correct zones?    This at times has thrown people off...

But currently I don't believe there is any delivery issues been the Cisco -->  Barracuda --> Exchange if the tracking logs show the email is accepted.


For the simple check look at the time zones on the clients/server...then check OWA compaired to Outlook  
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jsalisb4Author Commented:
Thank you.  I have been working on this all day... I looked a more logs and I found that there were some conflicts in the times.  I checked OWA as well and it matched up with the clients.  What I have narrowed it down to now is intermittent SMTP timeouts from the Barracuda to the Exchange server.  If I run the SMTP test it will pass one out of every 5 times.  It always fails on the SMTP 192.168.1.251:25.  When I telnet to port 25 from anything other than the Barracuda I don't have any problems.
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Rick FeeMessaging Engineer - Disaster Recovery EngineerCommented:
Ok SMTP timeouts will cause a delay for obvious reasons.

Well the default timeout for Exchange 2007 is 10 minutes...you can increase this but not sure if that is the resolution.

For forwarding from the Barracuda to Exchange are you using FQDN or IP?
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jsalisb4Author Commented:
I am using IP address.  No SMTP authentication.  I have verified that port 25 is wide open on my mail server...  Could this be a problem with the Barracuda?
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Rick FeeMessaging Engineer - Disaster Recovery EngineerCommented:
That is my guess at this point...are you up to the latest and greatest firmware for the Barracuda?    When is the last time the appliance was rebooted?    

Way outside chance it is a cable or port...

speaking of ports...locking down the ports to that of the network speed so there is no autoneg going on.
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jsalisb4Author Commented:
Helped me through some troubleshooting.  Thanks.
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jsalisb4Author Commented:
Yeah.  That is where I am at.  Thanks for your help!
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