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Windows 7 Outlook wont delete outgoing email


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Here are some things to check that I found.

The main reasons emails can get stuck in the Outbox include:

How to delete emails stuck in the Outbox​

The steps to delete emails stuck in the Outbox are:
  1. Set Outlook to work offline to prevent it from trying to send the stuck email
  2. Go to the Outbox folder, right-click the stuck email, and select Delete
  3. If that doesn't work, try dragging the stuck email to the Drafts folder, then open it and click Send

Deleting emails from a full mailbox​

If your mailbox is full and you're having trouble deleting emails, the key steps are:
  1. Try to delete emails from the Deleted Items folder, as they may be re-appearing there
  2. Look for ways to bulk delete emails, such as by date range, as the Outlook interface may not allow you to easily delete a large number of emails
  3. As a last resort, you may need to contact Microsoft support if you are unable to delete emails and regain access to your account
This may help

What to Do If You Can’t Delete Outlook Messages​


If your Outlook mailbox is full, the quickest way to free up some space is to delete old messages. All you need to do is select the emails you want to remove and then hit the Delete button. But sometimes, nothing happens when you hit Delete. Or worse, deleted emails keep coming back when you restart Outlook. If you’re looking for a solution to fix this problem, follow the troubleshooting steps below.

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Fix: Can’t Delete Messages from Outlook Inbox​

Empty the Deleted Items Folder and Log out​

When you delete an email, Outlook automatically sends it to the Deleted folder. While this folder has a smaller quota than your inbox, it can store hundreds of deleted emails. So, go to the Deleted Items folder, and empty it. Make sure to permanently remove all the emails stored there.

Then restart Outlook and check if you can delete inbox messages. If the issue persists, log out of your Outlook account and restart your device. Launch Outlook again, log back in, and check the results.

Hard Delete Stubborn Messages​

Alternatively, you can press and hold the Shift key while hitting the Delete button next to the message you want to remove. Outlook may sometimes prompt you to confirm your choice. Your messages won’t land in the Deleted Items folder; they will be permanently deleted.

Update and Repair Office​

If you’re also using Office, make sure to update and repair your Office files. Outlook is part of the Office Suite, so any issues affecting Office may plague the email client.
  1. Launch any Office app you want, click on File, go to Options, and select Update Options.
  2. Hit the Update Now button to check for updates.
    update microsoft office
  3. Then, go to Control Panel, select Programs, and click on Programs and features.
  4. Select Office and click the Change button.
  5. Run the Quick repair tool. If the issue persists, run the Online repair tool as well.
  6. Restart Outlook and check if you can delete unnecessary messages.

Use Outlook’s Cleanup Tools​

If you still can’t delete old emails from your Outlook mailbox, use the Cleanup tools.
  1. Launch Outlook and go to Info.
  2. Select the Mailbox Cleanup tool and filter the emails you want to remove.
  3. Then select Empty Deleted Items Folder.
  4. Restart Outlook and check if the problematic emails are gone now.

Run the Inbox Repair Tool​

You can scan and repair your Outlook inbox with the help of the Inbox Repair tool.
  1. Navigate to Program Files, select Microsoft Office, and go to Root.
  2. Then select your Office version and double-click on the Scanpst.exe file.
  3. Follow the on-screen instructions to run the repair tool.

Launch Outlook in Safe Mode​

You can also restart the email client in Safe Mode and delete the problematic message from there. Press the Windows and R keys, and type outlook.exe /safe in the new Run window. Hit Enter, and check if you can successfully remove those stubborn emails that refuse to go away.

Check Your Trash Folder Settings​

If this issue affects the mails you received from user groups, make sure the Trash option is enabled. Additionally, remove the deleted items from Outlook’s servers.
  1. Launch Outlook and click on Send & Receive.
  2. Select Send & Receive groups, and then Define Send & Receive groups.
  3. Click Edit, select your account, and go to Account Properties.
  4. Check the delete options available for the Deleted items folder.
  5. Make sure to select the Trash folder.
  6. Go to Advanced and enable the option that says Remove from server when deleted from ‘Deleted items.’


Not being able to delete old emails and declutter your Outlook inbox can be really annoying. Try emptying the Deleted Items folder and then log out. Alternatively, press the Shift key while clicking the Delete button to hard delete your emails. If the issue persists, update and repair Office, run Outlook’s Cleanup Tools, and the Inbox Repair Tool. Try launching Outlook in Safe Mode as well, and check if that helps.
It really depends on the source and what type of server you are using. If it’s IMAP or webmail and since you are using 7, it’s pretty much a given it’s a home system, here’s the deal. You are on a o/s that was EOL for some time now. Unless you are using a POP3 server, stick to webmail and forget outlook. Outlook itself has security problems and 7 is pretty much a wide open door. I would be very careful with email under your current setup..