Exch 2003 - Hotmail items stuck as "queued" in SMTP connector

New SBS 2003 R2 SP2, w/ Exch 2003 installation (SP2). All mail gets routed and queued correctly except to Hotmail. Mail to any Hotmail account usually sits in the SmallBusiness SMTP Connector Hotmail queue as “Queued” with “0” retries for anywhere from 40 minutes to 12 hours. Other items queue up behind it and then all send successfully at random intervals and are sent successfully.

Also, the queue icon is a plain folder with no “circle” indicating a status (such as check mark or arrow)

Maximum logging and wireshark sniffing show no attempt to contact Hotmail when the item is queued. It just sits there.

We’ve :

-      Installed and run the Exchange BP Analyzer (no issues found)
-      Manually connected to Hotmail SMTP via telnet with no issues
-      Verified DNS and SMTP through the firewall successfully
-      Run DNSStuff reports against the domain (reverse DNS issue identified and resolved 5 days ago)

The only thing that tools show as an issue is a blacklisting with Backscatter (but NDR reports have been turned off). If this were an issue though, wouldn’t I see retries and failures?

AV/Anti-Spam is Symantec Information Mail Security
TechShelfAsked:
Who is Participating?
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Alan HardistyCo-OwnerCommented:
A backscatter listing advises me that you are sending out NDR reports to invalid recipients.  Please have a read of my article and check your configuration:
http://www.experts-exchange.com/articles/Software/Server_Software/Email_Servers/Exchange/How-to-prevent-Spoofed-Emails-in-Exchange-2003.html 
Turning off NDR reports is not advisable - Filtering Invalid Recipients (if this is your only Exchange Server and your mail is delivered directly to your SBS box) is the best method to combat Backscatter.
Is the listing a current listing?
Hotmail also list people for no seemingly good reason, but getting yourself off the Backscatter site would be my first suggestion, then tackle Hotmail if the problem persists.
An alternative, it to set up a new SMTP COnnector to route Hotmail emails via your ISP's mail server instead of sending it directly.
0

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
TechShelfAuthor Commented:
Thank you, that's very good into and we did check all items but still no luck. I did another wireshark capture last night and I'm seeing TCP Lost Segment acks to Hotmail and one other MX host. We're going through a TZ 180 firewall. I would think that these could be the issue as well.
0
Alan HardistyCo-OwnerCommented:
0
TechShelfAuthor Commented:
This did not resolve the issue. it's still a problem.
0
Glen KnightCommented:
This question has been classified as abandoned and is being closed as part of the Cleanup Program.  See my comment at the end of the question for more details.
0
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Exchange

From novice to tech pro — start learning today.