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You won't get a pop-up because the SMF Forum software password save option is different. After you type your usename and password, in the next box click the arrow and select "forever".
Awesome, glad this is all set!
I have Office 2016 and Office 2013, not Office 365, although both 2013 and 2016 are "click to run". Everything I'm finding appears to be related to instant search. The only Microsoft support article I found "Applies To: Outlook 2016 Outlook 2013 Outlook 2010 Outlook 2007" and doesn't mention Office 365.
Fix search issues by rebuildling your Instant Search catalog - Outlook