Using classic Outlook for Windows in business environments
I have the same problem, and found it reported multiple times in multiple places. Microsoft and other responders however, seem to ignore the actual question - the whitelist is not working properly.
Why should we try all sorts of work-arounds? Come on MS, just fix the whitelist.
What most of us want is for MS to allow that we might know what we're doing - when we say whitelist this email address, just whitelist it, end of story, nothing more complicated needed. And then don't put whitelisted emails in junk.
Sounds very simple to do if MS actually wanted to do it.