AOL email intermittenly unable to reach SBS 2003 Exchange due to timing out

I have issues with AOL email making it to some users on our domain. It seems to happen intermittently and without any pattern that I can determine right now. I had issues with it a couple of years back made some adjustment to MS Intelligent Message Filter and then heard nothing about it until March of this year. It was reported at that time that emails from Corporate personnel (that happen to be AOL users) didn't make it through. However when I followed up on the issue their emails were then coming in fine. I figured it was just a time out issue since I had very little in the way of details from those users what had occurred. But last week I discovered that someone I know who uses AOL was having trouble sending me emails. Which makes me concerned because I don't know if the issue is related and certainly don't want the corporate users running into the problem again, certainly not if it can be fixed.  I'm Running SBS 2003 SP2 and we host our own Exchange.

I was able to find a situation similiar to mine except that it looks like that user had a Cisco firewall in place. I have a Sonicwall TZ 170.
When I ran the diagnostic tool on MXToolbox last week I did notice that it timed out and thought initially that might be it,  but refreshing it a dozen times doesn't recreate the problem. I've added it as a monitored event and haven't seen anything indicating that it's timed out since last week.

My friend the AOL user is currently getting email through to me and was able to get a copy of the AOL Returned Mail Transcript.


*** ATTENTION ***

Your e-mail is being returned to you because there was a problem with its
delivery.  The address which was undeliverable is listed in the section
labeled: "----- The following addresses had permanent fatal errors -----".

The reason your mail is being returned to you is listed in the section
labeled: "----- Transcript of Session Follows -----".

The line beginning with "<<<" describes the specific reason your e-mail could
not be delivered.  The next line contains a second error message which is a
general translation for other e-mail servers.

Please direct further questions regarding this message to the e-mail
administrator or Postmaster at that destination.

--AOL Postmaster



  ----- The following addresses had permanent fatal errors -----
<justauser@mydomain.com>

  ----- Transcript of session follows -----
<justauser@mydomain.com>... Deferred: Connection timed out with mail.pulsco.com.
Message could not be delivered for 3 hours
Message will be deleted from queue

As I mentioned earlier; what I gleemed from the post dealing with a similar issue as mine it appears they felt it was a firewall issue so I decided to take a look at the Firewall Logs. When I filter in on the event that looks questionable to me I get the following incidents being logged. The earlier events happened in March and my friend doesn't email me regularly enough to be able to say with any degree of accuracy when the issues occurred to them. Could this be related?

1 04/29/2011 00:00:26.032 Warning Firewall Logging SMTP POP-Before-SMTP authentication failed        
2 04/22/2011 00:00:26.896 Warning Firewall Logging SMTP POP-Before-SMTP authentication failed        
3 04/15/2011 00:00:26.736 Warning Firewall Logging SMTP POP-Before-SMTP authentication failed        
4 04/12/2011 15:33:41.224 Warning Firewall Logging SMTP POP-Before-SMTP authentication failed

Could it be that it is the Firewall causing the problem?
JeTopeteIT AdministratorAsked:
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digitapCommented:
I can't say this is it directly, but based on your comment, I'm guessing the firmeware is out of date too. This being the case, it's possible a firmware update would fix this issue. I have over 30 sonicwall units ranging from SOHO2's to NSA E5500 and I've not heard of this issue before. The sonicwall had an official firmeware release of 2007, but a Pre-Release was released in 2009. Sounds like the upgrade to the new sonicwall was a good idea.
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digitapCommented:
Are you licensed for any of the sonicwall security services (content filter, IPS, GAV, etc)?
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JeTopeteIT AdministratorAuthor Commented:
Not at the moment. It was proving more costly to renew versus upgrading so currently looking into upgrading the unit.
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JeTopeteIT AdministratorAuthor Commented:
I'll see if there's anything I can do about the firmware update. If that proves to be a dead end I will just let everyone know that AOL emails may sometimes not come through, at least until I get the new firewall purchased and installed. Thanks.
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digitapCommented:
Sure. Out of curiosity, what version of firmware is currently installed?
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JeTopeteIT AdministratorAuthor Commented:
SonicOS Enhanced 3.1.0.11-30e
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JeTopeteIT AdministratorAuthor Commented:
I know that it's important to keep firmware updated but in some cases I'm reluctant to do anything for fear of doing more harm than good. I'm sure you understand.
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digitapCommented:
That's a little behind, but doesn't seem to be much.

Current versions:
Standard OS: 3.1.5.0s Oct 2007
Enhanced OS: 3.2.3.0e Feb 2007
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digitapCommented:
Oh, indeed. I had a client once that relied heavily on a wireless network. Every time I upgraded the sonicwall, it would upgrade the sonicpoints. This caused loss in connectivity for all the wireless hosts until I upgraded the driver on each device. It was such a pain.
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JeTopeteIT AdministratorAuthor Commented:
Funny how somethings you can get by and never update the firmware and everything is okay until you retire the item. I imagine that was a hassle.
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digitapCommented:
yup...
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JeTopeteIT AdministratorAuthor Commented:
I could only hand out partials because I have not been able to test it out but the solution is at least pointing me in the right direction.
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