Bulk mailing stuck in the Outbox

Hi everybody,

One of our clients is having issue sending mass mailing through Outlook.
They retrieve all the contacts from a database and export the contact list to Outlook.
When hitting Send, only a subset of the mails are sent and the message stay in the outbox. The sent operation stay in progress for a long time and then the server times out.

The problem occurs for 2 different users associated with 3 different mailboxes. It was working properly before and the problem appeared without any settings change on our side.

To solve the issue we have already conducted the following troubleshooting:
- We have tried sending just one mail through each of these email adresses and they were successfully sent, which indicates that it is not a server connection problem.
- When the mass mail is being sent, we send another mail to one person and this mail is successfully sent. So the problem does not come from the mail quota.
- We have changed the outgoing SMTP server for those accounts to be one of our antispam platform GFI MaxMail and sent just one mail from each account that we were able to see in the logs. However when we sent the mass mail, nothing appeared in the logs. Therefore it is not an ISP or antispam issue.
- We have tried to delete and retrieve again the account on their Outlook clients, without any success.
- Moreover as the problem happens for 2 different users and 3 different accounts, it does not seem to come from Outlook.

It seems like the problem happens somewhere between Outlook and the antispam platform, which could come from the Exchange Server 2007.

Hence my question:
- Is there a setting in Exchange that could limit the number of email one user can send at a time ?
- Do you see any other reason why these mass mails stay in the outbox ?

Thanks a lot for your help !
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itGeniusAsked:
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NiceCuppaTeaCommented:
That's gonna be an exchange setting somewhere..... the thing is you can set the max recipients in a few places...

Mailbox
Organization
Connector (for Receive connectors only)
Transport server

Please check that the recipient limit is adequate in all of these places. This doc should help

http://technet.microsoft.com/en-us/library/bb310760(v=exchg.141).aspx
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NiceCuppaTeaCommented:
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itGeniusAuthor Commented:
Hi NiceCuppaTea,

Thanks for the suggestion.

At the moment the recipient limit setting is 500000
And maximum send size is 500000 KB
The emails sent does not exceed 300 recipients.

Would you have any other idea ?
Thanks
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NiceCuppaTeaCommented:
do you have anything logged on your exchange server or any outlook events in the clients event log that may point us in the right direction?
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itGeniusAuthor Commented:
Thanks for the update.

When taking a look at the Outlook logs, I saw the following error :
"The server responded 452 4.5.3 : Too many recipients"

It seems that your earlier idea was the good one, but the mails does not exceed 1000 recipients and their size is around 40KB.
So it should not reach the limit.

Or is there any other setting in Outlook or Exchange that limits the number of recipients ?
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itGeniusAuthor Commented:
Thanks, very informative.
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