Might be unrelated to your specific problem, but generating thumbnails, I 
do mine in template directly, using ImageKit. Upon upload, I resize the 
image to a good size or convert the uploaded image to format of my taste, 
say 2048x1080.

Then in template, I just do {% thumbnail '400x500' model.image_field %} and 
the thumbnail is generated on the fly. The on-fly-generated-thumbnail is 
cached, so no performance issue is encountered upon second request.

https://github.com/matthewwithanm/django-imagekit

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