If you notice that your email is stuck in the Outbox of Microsoft Outlook for your Microsoft Exchange account, you can do a few test to see what is the root cause of the issue.
* Password is Expired
* Network Account is Locked
* Connection is Lost
* Outlook is Corrupted
Test if Password is Expired
Using one of your installed free Internet browsers, navigate to the Outlook Web Access URL (ie. http://mail.example.com) that is used for remote email access and try to login to confirm if your password is expired. If it is expired, you will be prompted to change it. Once changed, save all your documents and logout of the computer and log in with the new password and Microsoft Outlook will open and send normally.
Test if Network Account is Locked
If the network account is locked, Outlook Web Access (ie. http://mail.example.com) will inform you that the password is incorrect. You will then need to contact your IT Department via phone but it is best to visit in person. If you logout and attempt to login, you should see a message saying that the referenced account is locked. If the IT Department is not yet open and you need to use the computer, you can temporarily disconnect the Ethernet cable (or WiFi) and login with the last know correct password then reconnect the cable or WiFi. Since the computer can not communicate with the ADDS, the stored credentials on your hard drive are used. This is the reason you must use a new hard drive and restore your data as viruses and malware that can steal your password could grab that information to send out SPAM and phishing emails. Please note that Outlook and shared drives will not work but the Internet and printing will be okay while the account is locked.
Test if Outlook is Corrupted
Sometimes, an Outlook profile will get corrupted so one option is to visit the Control Panel and create an additional profile (without deleting the bad profile) for the account that is causing problems. Creating a new profile for Outlook is also helpful for times when you cannot start Microsoft Outlook and receive Safe Mode error messages. I have never see a Microsoft Outlook Test Message when making a second profile for an Exchange account but I have seen it for POP3 and IMAP so do not be alarmed. If the alternative profile that you or the IT Department just created works, import any archive folders and setup rules from the bad profile. This is why it is important not to delete it the bad profile but leave it disabled.
If you do not know how to create an additional profile, try and move the emails to the draft folder. Once those stuck emails are in the draft folder, return to Outlook Web Access session (ie. http://mail.example.com) in the Internet browser and navigate to the draft emails folder. You can then open each draft email and send them off to your contacts.