Issues with sending tech's time to Payroll from Service Management

A former employee was rehired after several years of being inactive. After unchecking the inactive box, and checking the send time to payroll box in Service Management, we have had issues with his time sending to payroll consistently. It seems to pull time to payroll for a few weeks, then mysteriously the payroll box will be unchecked, and time will not transfer. I have confirmed that this is not something being done by human error, and he is the only technician we have this issue with. 

He did have to be re-added to payroll upon re-hire (same payroll ID as before). Could that have anything to do with it?

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