Exchange 2007 e-mails delayed

We use terminal servers and users sending large e-mails was a real problem before I configured my ASA to police SMTP traffic. Now users are not bothered anymore by large e-mails being sent, but another issue has come up. A couple of users are letting me know that they are receiving several messages that say their e-mail is delayed. I know this is a side affect of me policing the SMTP traffic. When to many e-mails are trying to be sent at once, the traffic is dropped and forced to retry. I would imagine the e-mail will eventually get sent, which is fine. However, it seems like many e-mails are just sitting in the queue and don't retry immediately. I am not sure if this is accurate or not but it looks to me like most e-mails were in the queue all day today. Is their a way to force Exchange 2007 to continuously retry e-mails? Can I push these out somehow so that as many are being sent and retried as much as possible?

Thanks,

Justin
JustinGSEIWIAsked:
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puppydogbuddyCommented:


Look at your firewall/AV programs (Turn them off temporarily to test).  There might be more than one problem, but if there is a firewall problem, it will be very difficult to identify other problems if your firewall is blocking email server communication.
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JustinGSEIWIAuthor Commented:
I am unable to disabled my ASA firewall and the exchange server has no firewall on it. I can turn off AV on the exchange server if you prefer. I have never had this issue before until I started policing SMTP traffic with my ASA. I am sure it is related to that. I was just wanting to know if their is a way to force exchange to continuously send e-mail instead of waiting like it seems to be doing.

Thanks,

Justin
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puppydogbuddyCommented:
Did you try turning off your AV program to see if that is the problem?  Assuming that you have resend mode on, your AV program may have a "rule"  that is blocking the Resend.  If it does, you need to modify that rule.
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JustinGSEIWIAuthor Commented:
I will disable AV to see if that makes a difference. Where can I check to see if resend is on?

Thanks,

Justin
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puppydogbuddyCommented:
In Outlook, Go to tools>options>mail setup>send/receive and set the various send/receive options, including scheduling an auto-send every X minutes.
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JustinGSEIWIAuthor Commented:
Sorry for the confusion. The issue is not with the client but with the exchange server. The e-mails are getting to the server just fine and are being sent by the client. They are being delayed at the server b/c of the SMTP policing. I don't think they are being immediately resent?

Thanks,

Justin
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JustinGSEIWIAuthor Commented:
I check the exchange queue and most e-mails have this error.

421 4.4.2 Connection dropped
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puppydogbuddyCommented:
To verify the retry setting, go to MS Exchange System Manager>Admininstrative Groups> First Administrative Group> Servers >Server Name > Queues > SMTP Connector and check if your
outgoing mails are in the queue with a status of 'Retry'.

If retry is turned on, try to determine if there is a pattern as to who the outgoing mail recipients (remote hosts) are that are dropping the connection.
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JustinGSEIWIAuthor Commented:
Sorry, I can't find the SMTP connector. What am I missing?

I don't believe their are any patterns. I have noticed that all e-mails having trouble have large file attachments. Some go through, some don't. I am thinking that so many are trying to go through on a slow link that they eventually time out b/c they are taking so long to upload. I have tried to find a way to adjust the time limit on sending outgoing mail, assuming that is the problem, but no luck yet.

Thanks,

Justin
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puppydogbuddyCommented:
Sorry, the SMTP connector is not for use with Exchange 2007.
                 See   http://www.amset.info/exchange/smtp-connector.asp

Will research outbound queueing problems on Exchange with attachments and get back to you.
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JustinGSEIWIAuthor Commented:
Thanks for your help. I have been searching the EE archives and have noticed many people with my same problem. Most of them come up with the answer that their is no good way to do what I want to do. It always comes down to recommending that large e-mails be outsourced to a service such as constant contact.

Please let me know what you find and what your thoughts are.

Thanks again,

Justin
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puppydogbuddyCommented:
Here is a troubleshooter that may be helpful to you.  After the web page comes up scroll to problem # 4 (Queues) about 3 pages down.
                 http://msexchangeteam.com/archive/2006/08/07/428616.aspx
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JustinGSEIWIAuthor Commented:
We came up with a work around for this issue. We decided that we are going to use http://box.net/ whenever we need to send e-mail attachments to large numbers of people. This service will allow our users to upload a file to their servers and then send the link to download the file out in an e-mail. The basic service is free and is well without our needs.

Thanks for helping.

Justin
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puppydogbuddyCommented:
Justin,
No objections to you closing out the question.  Glad you got your problem resolved.  In case you are interested, you might want to try this new Exchange Mail Flow Troubleshooter that I just became aware of :
                   http://msexchangeteam.com/archive/2006/08/07/428616.aspx
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JustinGSEIWIAuthor Commented:
Thanks puppydogbuddy! I appreciate your help!

Justin
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