A. A non-healing sore is concerning. You have to make sure that your dog does not lick the tip of the tail as that would impair healing. Your dog will need to wear a collar to prevent him from licking the tail. If the tail still does not heal by itself, you need to have a veterinarian have a look, as this could be caused by a tumor, bacterial or fungal infection. It could also be that the tip is irritating and your dog actually caused the sore initially.
A. First of all I would recommend taking him to the vet in order to have a look - a sore that has been there for a while is probably infected and needs antibiotic treatment.
Some dogs will injure the tip of their tail, and by waging the tail constantly it will hit the walls (or other things) and will keep on re-opening time and time again. This is a very frustrating situation - when bandage doesn't help and it keeps reoccurring all the time, after a few months I usually give up and advise to amputate 2/3 of the tail.
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