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  I too have a puppy that does this.  It totally freaked me out when we brought him home and he did it the 1st time.  I took him to the vet and the vet said I needed to constantly monitor it (due to my pup's small size and some lethargy) as it could be a sign of liver shunt.  I was mortified and worried to death.  I kept a check on it and started writing down when he would do it.  (If a pup is doing it after eating that can be a sign of the protiens in the food causing the issues  re: liver shunt).
 For my pup, I would even pick him up and massage his little head in my hands to try to ease whatever it was that was bothering him.  I have done alot of research on it and still don't have an answer for why my pup does it.  (Yes, we did have a blood test done for liver shunt that came back w/ great levels so doesn't appear to be liver shunt).  Now 2 1/2 months later, he still does it but it appears to be more of a scratching himself action rather than a head-pressing.
 
 Also his breeder told me that his mom does it as well (more of a scratching type action).  I am continuing to monitor it, but the frequency my pup does it has diminished and I remain convinced it is just a body scratch thing that some puppies do.
 
 Keep us updated if you find a cause or reason.
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