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"The operation failed." Sending email using Contact Items in Outlook 2003

I am using Microsoft Outlook 2003 to send a message to recipients in a Contact Items list in the BCC field.  When I hit send Outlook reports "The operation failed." and doesn't provide any further information.  Is there any possible way to find out why Outlook is failing, a possible log file?

Things I have tried:

1) Turned off Microsoft Word as the default editor.

2) Tried sending to fewer contacts in the BCC field, sometimes sends, sometimes doesn't-- there is no pattern.  Could there possibly be some corrupted entries in the Contact Items that I cannot see?

3) Checked Exchange Server settings for Maximum KB per message and Maximum recipients per message.

Other things to take into consideration:

1) We have just migrated from Exchange 2000 to Exchange 2003.

2) We have just updated all are copies of Microsoft Office 2003 via officeupdate.microsoft.com.  Should I possibly uninstall SP1 and the updates, and if so how do I do so?

3) The email is in HTML format and contains 2 attachments totallying < 2 MB.

I have read most of the solutions regarding the "The operation failed.' error message however none of them have helped solve this bizarre issue.  Any help would be greatly apreeciated, I am in a bind to have my fellow co-workers send out an email to several hundred contacts but were receiving this unhelpful error message.  Thanks!
1 Solution
apsingletaryAuthor Commented:
Update: I appears that if you break the Contact Items list into Distribution Groups the message will send.  This then leads to the question of why I am not able to just add/send directly to the list of Contact Items in the list directly?
sounds like a corrupt profile, please create a new profile!
Just as another note about this; We run PGP for our Outlook clients. Stoping the service and then closing / opening Oulook helped one user. Not sure if this is a fix, but at least helped out for the day.
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I had this same error in Outlook 2007, I only had one message that would not send.

I appears that outlook did not like one of the addresses from the N2K cache (outlook address cache that populates as you type from your history). I entered the addresses manually and the email sent properly.

I'm guessing that one of the addresses in the N2K cache was corrupt, good think I only had to retype 3 addresses.
i have tried creating a new profile as well but it didn't work...i need to send out our weekly newsletter and still no success how to solve this problem

I am getting a similar issue in Outlook 2007 with only one distribution list. I have recreated the list and still get the Error  "The operation failed" when trying to send. I have corrected the invalid email address in the list but still get the same error.

Found my issue was with a recipients address that had a ' in her name.

Odd thing with this was if I emailed only her the msg sent with out error but if I add her to the DL I get the error again.

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