Outlook Microsoft Outlook 2007 unable to send to multiple users

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one user is unable to send to multiple contacts from outlook 2007. The message remains stuck in the inbox.
The pc is running windows xp service pack 3 and Outlook 2007 (12.0.6423.1000) SP2 MSO (12.0.6425.1000)
 
Is Outlook connecting to an Exchange server or POP3, etc?

Have you verified all the email addresses of those contacts?
Can the user send to EACH contact indvidually without problems?

My first thought is that there may be an issue with one of the contacts' email address, though generally that would prevent you from even sending if connected to an exchange server. Not so sure about POP3, IMAP, etc.

If it's not one of the contacts, could you provide some more information about your email server?
 
The user can send to each individual contact without problems. we are connecting to a pop3 and we use hmail.
 
With POP3/SMTP, I would double-check the syntax of how the multiple email address are added, to ensure it has no extra spaces or incorrect characters, etc.

You didn't mention attachments and I would assume you have tried to send an email with just a simple test email w/no attachments. If there is an attachment, then perhaps size of the attachment or space available under that account is an issue.

I have noticed that some have said that using Contact addresses have caused the problem for them (suggesting perhaps something is corrupt/wrong with their contacts - perhaps a recent migration?). So when they hand entered the addresses, the email sent just fine (kind of goes back to my syntax check).

Other possibilities:
http://www.howto-outlook.com/faq/messagestuckinoutbox.htm
 
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