Using New Outlook on Windows for professional communication and productivity
Hi Kristen,
New Outlook includes a Reopen items feature under Settings > General > Start up, which can be set to ask whether to reopen previously opened items or to reopen them automatically.
However, based on my own testing, the feature may require some time before previous session information is fully reflected. I also noticed that the behavior can vary. In some cases, Outlook prompted me to reopen items from my previous session, while in other cases it did not.
I would suggest waiting up to 24 hours after enabling this feature and then testing again to see whether Outlook is able to restore previously opened items. Also, do not select "Remember my decision", as this allows Outlook to continue displaying the prompt to reopen items from your previous session, giving you the opportunity to restore previously opened email windows when the prompt appears.
If the behavior remains unchanged, it is possible that you are experiencing a similar situation to other Outlook users, where previously opened items are not always restored after an unexpected restart or crash, even when the Reopen items feature is enabled. You can review a related discussion on the Feedback Hub here:
When Outlook crashing, previous session emails do not re open.
Consider upvoting the feedback and sharing your experience there, as additional feedback can help increase visibility with the product team.
I hope this information is helpful. Let me know if you have any questions.