Free Transform Tool- Sideways Scaling?

You probably won't really understand me here, but I've been using the free transform tool, I'm still pretty new to this program, but I'll say when selecting something and hovering your mouse to the top of the selected object there's an arrow with 2 sides going left to right. I, to myself, call this sideways scaling. Before, it was perfect. But I think there's been a changed  setting I don't know of an when I sideways scale, the object snaps to the farhest point. It used to be smooth and I could set it to any point, but now it just doesnt seem to work the way I want it to. Though I could also tell that this must be something about tranformation points as when the transformation point is directly in the middle, it goes smoothly, but when in the transformation point I want it to be set to, it just does it again.Heres an example