I have a user that keeps getting promted for security questions everytime he logs in? does anybody know how to fix that issue?

Do they have their browser set to clear cache/cookies on browser close? I've seen that a couple times.

No, because about 50 people use that exact same computer/browser to log in and out through out the day, when they have to renter work order results and such.. and only one eomployee experiences this problem.