Asset Warp Tool Issue

Whenever I try to use the Asset Warp Tool on a still image, some sections of the image turn black whenever I move the pins around. I've gone through different attempts to fix this issue, such as:

1. Smoothing the Artwork

2. Changing the Size of the Art

3. Changing Pin Locations

but I haven't been able to find a solid answer. I would really appreciate the help in trying to find out how to get this under control.

Thank you!