Occasionally sent items will stop appearing in the Sent Items folder.

Enable Saving Sent Items

For POP/IMAP mailbox please refer to the Knowledge Base article Outlook 2013/2016/2019 IMAP: Mail Is Not Populating.

For Exchange mailbox, follow the steps below:

Outlook 2010/2013/2016/2019:

  1. Log in to your mailbox in Outlook.
  2. Navigate to File > Options > Mail.
  3. Uncheck the Save copies of messages in Sent Items folder box.
  4. Click OK.
  5. Navigate to File > Exit to close Outlook.
  6. Open up Outlook again.
  7. Navigate to File > Options > Mail.
  8. Check the Save copies of messages in Sent Items folder box.
  9. Click OK.

Outlook 2007:

  1. Log in to your mailbox in Outlook.
  2. Navigate to Tools > Options > Email Options.
  3. Uncheck the Save copies of messages in Sent Items folder box.
  4. Click OK, then OK to save your changes.
  5. Navigate to File > Exit to close Outlook.
  6. Open up Outlook again.
  7. Navigate to Tools > Options > Email Options.
  8. Check the Save copies of messages in Sent Items folder box.
  9. Click OK, then OK to save your changes.

Sent items should now start appearing in your Sent Items folder.

Troubleshooting

If the steps described above do not resolve the issue, it might indicate a synchronization error or a corrupted Outlook profile. To resolve it, follow the steps below.

 

Disabling Cached Mode

Outlook 2013/2016/2019

  1. In Outlook, go to the File > Account Settings, then click on Account Settings again in the drop-down list.
  2. In the Email tab, select your Exchange account and click on Change.
  3. In the Exchange Server Settings window, check Use Cached Exchange Mode and click on Next.
  4. You should be back at the Email Accounts window. Click on Finish.

You should see a notification window that advises you to restart Outlook in order for the change to take effect:

In case this step resolves the issue, you can safely enable Cached mode again.

 

Outlook 2010

  1. In Outlook, go to the File > Account Settings, then click on Account Settings again in the drop-down.
  2. In the Email tab, select your Exchange account and click on Change.
  3. In the Exchange Server Settings window, check Use Cached Exchange Mode and click on Next.
  4. You should be back at the Email Accounts window. Click on Finish.

You should see a notification window that advises you to restart Outlook in order for the change to take effect:

In case this step resolves the issue, you can safely enable Cached mode again. 

 

Outlook 2007

  1. In Outlook, go to Tools > Account Settings.
  2. In the Email tab, select Microsoft Exchange Server and click on Change.
  3. In the Exchange Server Settings window, check Use Cached Exchange Mode and click on Next.
  4. You should be back at the Email Accounts window. Click on Finish.

You should see a notification window that advises you to restart Outlook in order for the change to take effect:

In case this step resolves the issue, you can safely enable Cached mode again.

Repairing the Outlook profile

If after restarting Outlook the issue persists, the Outlook profile should be repaired by the Scanpst tool.

How To Use The Inbox Repair Tool (scanpst.exe)

Recreating the Outlook profile

If after repairing Outlook profile and restarting it the issue still persists, the Outlook profile should be recreated:

Guide: How Do I Connect A Mail Client To My Mailbox?