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Please see Microsoft article: Delay or schedule sending email messages
Note: that the Outlook Client needs to remain open for emails to be sent on a delayed schedule. Computers may reboot due to patching at any point in time and the emails will not be send till Outlook is opened again.
Troubleshooting steps:
- Record the From and To emails addresses
- Look in the user's Outlook "Outbox" to see if email has not been sent
- Look in the user's Outlook "Sent Items" to verify email was sent
- Record the timestamp that the email was sent
- Ask for when the other person received the email and record time