Hi, I'm Diane and will be happy to help you today.
Which version and build of Outlook are you using? See File, Office Account for the information.
In File > Options > General - do you have the option to change the setting?
I've seen a few other reports that Outlook 2019 is bringing up that dialog but does not have the option to change the setting. I emailed my contacts at Microsoft about it and am waiting to hear back.
I suggested to the other users to try this key - only one responded back and said it did not help. If you try it, restart Outlook after adding the key.
HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\Preferences
DWORD: ReopenWindowsOption
Value: 1
-- Diane
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