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Hi ScottSeifert,
From your post, I notice that when restarting the Outlook client, you want to keep the email windows you opened last time. Please let me know if I misunderstood anything.
It’s not feasible to achieve this feature in the Outlook client. You may find some workarounds in other forums. I have also done some tests and found that these workarounds do not work for everyone. So we recommend you submit feedback to our relevant team via: http://office365.uservoice.com/forums/273494-outlook-and-calendar. Many features have been designed or upgraded based on our customers’ constructive comments. We appreciate your time and efforts.
Regards,
Aaron