I seem to have a problem when trying to model a helmet from both front and side view with the object being horizontal instead of vertical in both sides
The first one is the top ortho, so it means from “above”. Switch to front ortho (Numpad 1) for your left view.
Edit: If you want the image projected on the appropriate sides, you have to assign the axis for each view. For the left one that is supposed to be front, attach the image to the front (Y+). Add another image and attach it to the left (X-)
Thanks buddy. Been wondering for a while