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Remember when you treat him with Frontline not to let him get wet for at least 24hrs. And, unlike what someone else has said, I've heard you are not supposed to rub it in, but let it sit on the skin.
If he keeps getting reinfested, it sounds like you probably have fleas in the house. I think it would be impossible to have a dog with fleas and not have them living on his sleeping areas.
Try the Frontline powder that people have suggested. Do it before you dose your dog with the Frontline and then probably again after... I'm sure the instructions will tell you about stuff like that.
Like someone said, fleas are building up a tolerance to the usual treatments. If frontline isn't doing it, ask your vet to give you a different flea treatment.
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