For Windows 8.1 & 10 and Outlook – when the delete confirmation dialog doesn’t pop up, here are the steps to make sure it does.

Set Windows 10 to display delete confirmation dialog

  • Right click on Recycle Bin on the desktop, select Properties

Select ‘Display delete confirmation dialog’ and click ‘OK’.  (see screenshot of the dialog box below)

confirmation-dialog

Set Outlook to display delete confirmation dialog

  • In Outlook, select File -> Options.
  • Go to Advanced in the left pane.
  • Scroll down to the Other section.

Make sure the Prompt for confirmation before permanently deleting items option is checked.

outlook-options