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User Gets "Set Up Security Questions" every day he logs in

Knowing this makes the most sense as an issue with browser cache or cookies - we've tried all things there. Try a different browser - same issue. Try a different computer - same issue. His main computer is a mac and main browser is Chrome, but we had a Windows PC we had him try it on and issue persists. Obviously have cleared browser cache, still persists. Anyone have any insight here? User is frustrated he has to deal with this every morning. He's the only user in our org experiencing these issues.

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