Exchangeg 2003 Queues in Retry

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Our Exchange 2003 is having major problems with outbound delivery delays.  There are several messages in the queue in retry mode.  Some messages are delivered without a problem, however a majority of messages end up in retry mode, and eventually fail.  There is no smarthost being used.  The SMTP Virtual Server is configured to use several external DNS servers for lookups.  Any ideas?
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From your description it sounds like these are outbound emails only, no internal issues.  You mentioned seversl DNS servers.  This isn't necessarily a good thing, 2 or 3 that or close to home with good records is the best route.  In other words, unless you use a garage ISP you should use your ISP's DNS.  It's the closest responder.  Furthermore, ISP's sometimes limit DNS responses to clients that aren't on thier network.
I assume this all worked at one time.  What is your Internet connection?  If it's something like DSL or Cable these are best effort connections that can often give intermittent problems for higher need services like email and VPN.
You should check the reason why messages aren't being delivered. If you click the queue that has problems you can see the reason in the bottom of your exchange management console under 'additional queue information'
Could you also post the NDR report you get when the message failed to deliver?

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Another possible reason - has your IP/Domain been added to a SPAM blacklist?


Here is the typical NDR report:
Action: delayed
Status: 4.4.7

Every queue says "The connection was dropped by the remote host".  It seems to be related to timeout issues.  Any thoughts?

I checked the SMTP log, and seeing this quite a bit:

Normally, error 4.4.7 indicates there's a problem on the receiving side. Can you try to mail through a smart host to see if it makes a difference?
Still could be a SPAM rejection or poor Internet connection.  Did you check the blacklists?  Do you run a single ISP or load balance?
The problem turned out to be our Cisco ASA:

The Mailguard feature was causing the issue.  Mailguard was always enabled, but after a recent IOS upgrade, something must have changed and was causing the problems.
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