This feature does not work in the following situation:
- Outlook is closed
- A mailto: link is clicked in a browser
The new email message opens by itself. I noticed the "reopen items" dialog box did not appear like I was expecting it to. I did not close the new email message, and then tried to open Outlook as a whole. Unfortunately, everything open previously does not reopen.
I found this out by accident, and it is very annoying.