Here is my problem: I have a plane with an image texture on it. The image texture has an alpha channel, and the image is currently on my plane. I want the shadow to follow the outline of the tree on the plane, as you can see in the image below. However, the shadow that is cast is the shadow of the plane, ignoring the alpha channel.
That’s it! This fixed it, thank you so much. I did check that earlier before posting but didn’t notice it as my sun light was set to 35 degrees. Thanks for pointing it out!