Outlook:emails stay in outbox.

When sending emails via Outlook emails are not sent. Emails stay in outbox.

 

Have you properly set up the account as per your ISP (Internet Service Provider) settings?

Here is a quick Guide on setting up an Outlook account: http://products.secureserver.net/email/email_outlook.htm

Also whilst Outlook is open confirm that it is online, usually shown in the bottom right hand corner of Outlook

 

In addition to what Kimsland said, there are any number of reasons why emails stay in the outbox. Are you assuming they aren't being sent because they are still in the outbox or are they actually not going out? I know it sounds a little far fetched but the sent items folder could be full [I think the limit is around 16,000 messages].

You may also want to try the troubleshooting at http://support.microsoft.com/?id=195922