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It looks like it's a weird corner case in when we reset the current year's service time. It seems like when he signed with you, some of the service data was updated, but the "current year" calculation wasn't. Once he gets past the 172 day "season" we stop adding to their overall service time calculation, hence why it's not updating.
We can investigate how to avoid this in the future. You can simply edit him after the season to give him his year of service if you want to keep that updated properly.
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