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Please keep in mind:
Most likely network issues. When you want to upload something the system has a limited time to complete this process. Bad network (internet speed, server network, etc) highly affects this.
Is there something I can do to increase the timeout limit?
Also, to be clear, the images upload fine.
So you're telling me that resizing an image from 6000x3000 to 6000x3000 (the same) isn't working because the network is timing out? Why does the resizing to medium at 500 width work on the same image? (wouldn't that be MORE processing than resizing to the same size?)