Last modified June 20, 2016
If you see messages piling up in your Outlook outbox, we want to get those messages sent as quickly as possible.
The following solutions are listed from the quickest to the most in-depth option.
If you’re using Office 365 for business, let us fix the problem for you
You can run Support and Recovery Assistant for Office 365 to let us fix the problem for you. If you’re not using Office 365 for business, or the Support and Recovery Assistant app doesn’t resolve your problem, see the next section.
Let us fix your issue
Check the bottom of your Outlook window
If you see Disconnected, Working Offline, or Trying to connect…, Outlook can't reach the email server to send your mail.
Choose Send/Receive > Preferences > Work Offline to toggle between offline mode and online mode. You may need to open the message and send it again, or choose Send/Receive.
If that doesn’t fix the problem, see the next section.
Check to see if your messages contain large attachments
Go to your Outbox and then open the stuck email messages. Start with the oldest message first. If that message has an attachment that’s larger than 5MB, delete the attachment and either attach a smaller file or attach a link to the attachment. You can then try to send the message again. If that doesn’t fix the problem, see the next section.
Have you changed your password recently?
If you've changed your password on the website for your email account, you'll need to change it in Outlook, too.
Choose File > Account Settings > Account Settings.
On the E-mail tab, choose your email account, and then select Change.
Enter your new password in the Password box, then choose Next > Close > Finish.
Note: If you sign in to your mail account with the same credentials that you use to log on to your network, you won't see the screens shown here. You'll need to change your email password by changing your Windows network password. Press Ctrl+Alt+Delete, choose Change a Password, and follow the instructions Windows provides.
Once you’ve changed your password, you might need to open and send the message again.