I had an Executive Director at a company schedule his emails by months in advance using the delay send option. He was very concerned that his outbox emails wouldn't come over to his new system. He only had 21 of them, so this method may be cumbersome for people that have 100+ emails sitting in there.

Steps I took to get the emails moved to his new system and keep the delayed send settings:

- Documented the delayed send settings for each message with screenshots. (precaution just in case)
- Exported the emails from his "Outbox" on his old PC to a .PST file
- Created a new folder in Outlook and imported the Outbox emails from his old PC.
- Opened each email, verified the delayed send options were correct and clicked send.
- Checked the Outbox on his new PC and verified all the messages were there and ready to be sent.