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There are a couple of things that could be a problem.
1 . He might have a problem with his anal glands and have pain in that area. The anal glands are at 10 and 2 like a clock beneath the tail. The often get overfull and need to be expressed. If you suspect this, you can see your vet or groomer to do the task.
2. He might have a tail injury or have pain in the tail itself. If this is the case, your vet might want to give a steroid injection to help hasten healing.
I would keep an eye on it and see if it improves. If not, you will want to see the vet within the next 24 hours.
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