Sending mail "Stuck" in Outbox??

I have mail that is not being sent to valid email addresses. They are still in my outbox.
3 Questions:
1) How do I force mail to be resent from the outbox?
2) If there are 3 messages in cue & message #1 has an invalid email address will it prevent messages numbers 2 & 3 from being sent?
3) If I put 10 correct email addresses in a recipient list and one address is incorrect, will the mail be sent to the 9 correctly typed email address and alert me that one address was unavailable or will the one incorrect address prevent the email from going out?
Thanks in advance!

> 1) How do I force mail to be resent from the outbox?
By fixing the problem that prevents it from being sent. There is no way to answer that with the information you’ve provided. What’s the problem exactly? What error messages do you get, if any? Are this mail account and the associated outgoing (SMTP) server provided by your ISP or by someone else?
> 2) If there are 3 messages in cue & message #1 has an invalid email
address will it prevent messages numbers 2 & 3 from being sent?
AFAIK, a message stuck in Outbox doesn’t prevent other messages from being sent. The reason why the message stuck in Outbox couldn’t be sent is irrelevant — unless it’s the same reason the other messages cannot be sent either, of course.
3) If I put 10 correct email addresses in a recipient list and one address
is incorrect, will the mail be sent to the 9 correctly typed email address
and alert me that one address was unavailable or will the one incorrect
address prevent the email from going out?
The message will be either sent to all recipients or not sent at all. Whether all the recipients receive it is another story. If Mail puts the message in Sent, that means the outgoing server told Mail that the message would be delivered (to all recipients). If the message remains in Outbox, the message wasn’t sent to any of them.

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Hello Lilikoii,
Thanks for using Apple Support Communities.
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Hi
I have some users who use a shared mailbox [email protected]
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If you don't know Powershell: http://help.outlook.com/en-us/140/cc952755.aspx
Best regards George

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How about sending emails to external via OWA on your laptop and desktop?
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For your convenience:
http://community.office365.com/en-us/default.aspx
Also suggest collecting detailed error from App log.
Thanks
Mavis
Mavis Huang
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Hello,
We are currently experiencing some weird behaviour in Outlook 2013 since we added Shared Mailboxes.
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Sending mail "Stuck" in Outbox??

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