Using classic Outlook for Windows in business environments
I'm on build 2306. Is this the reg key in question?
HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\Preferences
DWORD: ReopenWindowsOption
Value: 1
Yes.
Some users that updated to 2306 have reported that the key was not already in the Registry and had to add it and the value.