Overview
Your Classic Outlook app must stay open during the delay window for the email to go out. If you close the app, the emails will remain paused in your Outbox until you reopen it.
Issue
I need to delay an email being sent from my outbox.
Troubleshooting
Click the Settings icon (the gear symbol) in the top-right corner of the window.
Select Mail from the left-hand column and click on Compose and reply.
Scroll down until you find the Undo send section.
Move the slider to select how long Outlook should pause before sending (up to 10 seconds).
Click Save at the bottom.
Whenever you hit send, a small "Undo" button will hover at the bottom of your screen for those 10 seconds. Clicking it stops the email and reopens your draft.
If you experience issues with this Outlook function, contact the help desk at 913-288-7479.