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O365 issue requesting authentication multiple times when recording session

I keep having this pop up and then it end up not running the recording properly.  It pops up sometimes just once and other times twice and causes playback not to perform properly.  I can't tell you how many recordings I've done where it will work, then not work and that isn't including the trying to verify a download.  I'm just over here pretty much banging my head against my desk, so any help would be great.

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