Steps to reproduce the behavior

1. Activate a theme that uses a custom header image:
2. Go to My Site > Appearance > Customize > Header Image
3. Click on Add new Image
4. Select and image and then click on Select and crop

What I expected to happen

To be able to crop the image to the correct header size and then save it to the header

What actually happened

When you get to the next screen, there is no cropping selection. Dragging across the image to create a selected section results in Drop image. Clicking on Crop results in the error {file name} There has been an error cropping your image. if there is a Skip Cropping option and you select it, it does not update the header image

There is a video of my test site here: https://d.pr/v/0kpjbn

Context

Customer reported this in #29153016-HC

Browser / OS version

Mac OS 10.15 / Chrome 89

Customer was using Windows 10 with Chrome 83

Is this specific to the applied theme? Which one?

First reported on Dynamic news, but I have also tested Dara and Intergalactic and had the same issues

Does this happen on simple or atomic sites or both?

Simple. The cropping function works as expected on AT sites

Is there any console output or error text?

No

Level of impact (Does it block purchases? Does it affect more than just one site?)

It affects more than one site, but doesn't seem to prevent other editing of the site

Reproducibility (Consistent, Intermittent) Leave empty for consistent.

Screenshot / Video: If applicable, add screenshots to help explain your problem.