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How are things going with the Pup? Sounds like you were getting on the right track. You can definitely consider some of the howling behavior normal with a pup and German Shepherd puppies in particular are prone to this.
One thing that I would like to stress, just like Chris, is to be sure not to overpet and coddle. This is by far one of the biggest factors that makes it very difficult for the pups to deal with seperation. I have known lots of German Shepherds who can barely tolerate being seperated from their owners when the owners are actually present but not within reaching distance – nevermind out of site. When they are pups is when you really set the pace for this.
