This is a problem we have with Peanut. We did all the proper research before even touching his little butt. And after learning about everything that we could, we eventually had the vet show us how to do it so that it can be done right. It's best to exress it while giving your little one a bath. It's least umpleasent that way, much like a pimple honestly. If the dog generally has regular (not so soft) poop then the gland should express itself, and it really shouldn't be a consistant problem.
But like has been said before, try and not mess with the gland too much, overexpressing the gland can lead to more severe problems
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