Fix: Outlook Emails Get Stuck in the Outbox

Here is what to do if your Outlook emails get stuck in the Outbox in Outlook.

First: Try re-sending

  • Go to the Send/Receive tab and click Send All. You’ll see a dialog box showing the results of the process, and your email might exit the outbox.

If that doesn’t work, then:

  1. Make sure Outlook is online.
  • In your status bar at the bottom of your Outlook message, you’ll see a status of “Disconnected” or “Trying to Connect” that could explain why your messages aren’t sending.
  • Check your internet connection, wait a few minutes to make sure it’s not a momentary outage, and try again.
  1. Check your mail settings.

If you’ve set a rule to delay message sending, you will see your mail in the outbox for awhile.

  1. Is your message being slowed down by a large (or multiple) attachment?

Depending on the speed of your internet service connection, if you’ve attached a large file (or multiple) to your email message, you may see it sitting in the outbox because it’s simply taking a while to send, and it may be blocking all subsequent emails from sending.
Email is not meant for sending large documents or photos: You 'd be better using a cloud service like OneDrive or Dropbox to collaborate on large files instead.)

  1. Use the correct password.

If you recently changed your password, you’ll have to make sure Outlook “knows” the correct password.

  • From the File tab
  • Select Account Settings and Account Settings again.
  • Select your account and click Change. Under Logon Information.
  • In the Password box, type your new password.
  1. Re-send directly from the outbox.

If your Outlook settings are configured a certain way, you won’t be able to send emails if you’ve opened or clicked on them after you’ve clicked send, i.e. if you’ve marked them as read from the outbox

If this is the case:

  • Open your email from the outbox.
  • Browse to a new folder so you won’t automatically re-mark it as read.
  • Click Send on the stuck email.

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