I hold it different ways depending on what I'm doing. I think when I "click" the tip I do tend to move it into a more vertical position though. I'll have to pay attention to it when I use it next to see. I will say that yesterday I sat my son down at it and had him play around in PhotoShop to see how he took to the tablet as well as the application. He had no problems with the stylus right out of the gate except for two things. The first was that he kept trying to use it like a mouse and picking up and dragging it, and second was he kept hitting the stylus button. Once I showed him how the tablet mapped to the screen and that the stylus would "jump" the cursor he was zooming right along. He didn't have any clicking issues either as he moved from one tool to the next and selected layers and such.