@musicbydavidrosen The problem you're describing is caused by the direction of the path. When you create a path with the Pen tool, it has a beginning and an end. If you draw the path clockwise, the text will follow the curve as you expect. However, if you draw it counter-clockwise, the text will appear upside down or reversed. You could select the path (black arrow), in the options bar, look for the path operation drop-down menu and click reverse path. our text should now reorient itself correctly.