Should i be able to feel when the needle enters my skin during acupuncture?

Maybe: Depending on needle size, practitioner technique, location of insertion point, and your sensitivity you may or may not feel it.

Sometimes: Needle location, diameter, length make a difference. Usually, if there is any discomfort it will be when the needle is introduced initially into the skin. However with good techniques such as "push finger" and wodging there is often no sensation. Sometimes my patients are very surprised when they ask when I am going to put the first needle in and I have already placed a dozen or more needles.