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My messages won’t send

Applies to: Outlook for Office 365, Outlook 2019, Outlook 2016, Office for business, Outlook 2013.

Last modified April 12, 2017

If you see messages stacking up in your Outlook outbox or people you’re sending messages to aren’t receiving them, test the following methods to resolve the issue. These methods are arranged in order of fastest to the most detailed.

Screenshot showing a message stuck in the Outlook Outbox

If you’re using Office 365 for business, let us fix the problem for you

You can use Microsoft Support and Recovery Assistant to allow us to rectify 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, read the next section.

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Is Outlook disconnected? 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.

Outlook status bar showing that Outlook is disconnected from its mail server

Select Send/Receive > Preferences > Work Offlineto switch between offline mode and online mode. You may need to open the message and send it again, or pick Send/Receive.

The Work Offline button in Outlook 2013

If that doesn’t fix the problem, check the next section.

Make sure you’re connected to the Internet

If your Internet connection is disrupted, Outlook won’t be able to send your messages.

  1. Open a browser, such as Internet Explorer, Edge, or Chrome.

If that doesn’t fix the problem, see the next section.

  1. Try typing one of the listed websites in the address bar:
  1. If you’re unable to access either of those two websites, read Troubleshoot network connectivity problems in Internet Explorer.

Do your messages contain large attachments?

Some e-mail providers (such as your ISP or even Gmail) won’t let you send messages larger than a certain size. Inserting pictures and large attachments to your message can stop you from sending that message (and any messages sent after the large message).

Find your Outbox and then launch the stuck e-mail messages. Begin with the oldest message first. If that message accompanies an attachment that’s bigger than 5MB, delete the attachment and either attach a smaller file or attach a link to the attachment. See Attach a file to an email in Outlook for further details.

Now attempt 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 e-mail account, you’ll need to update it in Outlook as well.

  1. Select File > Account Settings > Account Settings.
  2. On the E-mail tab, pick your e-mail account, and then press Change.
  3. Type your new password in the Password box, then pick 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 displayed here. You must update your e-mail password by setting a new Windows network password. Press Ctrl+Alt+Delete, select Change a Password, and follow the instructions given by Windows.

Once you’ve created your password, you may need to launch and resend the message.

Contact your antivirus software’s help desk

Some antivirus programmes run e-mail scans. If a virus is detected, your antivirus software may temporarily suspend you from sending or receiving any new messages until you remove the virus.

Repair your Outlook programme

Occasionally, the Outlook programme may require maintenance. Repairing is a basic process, but could take a maximum of 30 minutes to complete. Fort more details, read Repair an Office application.

Repair your Outlook profile

A profile is a collection of settings that determines how Outlook functions. It contains a log of your accounts, autocomplete details, and your name and initials. To repair your Outlook profile or produce a new one, see Fix your Outlook email connection by repairing your profile.

Start Outlook in Safe Mode

Often, one of Outlook’s add-ins will go haywire crash and block your e-mail messages from sending. Disabling all add-ins can be done by opening Outlook in Safe Mode. If you can send e-mail while Outlook is in safe mode, setting up a new Outlook e-mail profile should enable you to send e-mails again.

To launch Outlook in Safe Mode, tap the Windows key. In the search box, input outlook.exe /safe and press Enter.

For more details on creating a new e-mail profile, see Create an Outlook profile.

Run the Inbox Repair Tool

For several types of e-mail accounts, Outlook saves your messages in a Personal Folders File (.pst file). You can repair this file by running the Inbox Repair Tool. This repair should take about fifteen minutes. For more details, see Repair your Outlook personal folders file (.pst).

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This information was compiled using information courtesy of © Microsoft 2020. All rights reserved.

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