Upload keeps failing, but I can resume where it left off

Everytime I do an upload, the upload fails about 5 minutes into the upload. But if I click "retry" it resumes the upload where it left off. I get this occurrence on firefox, chrome, microsoft internet, and on mobile firefox. This heavily hampers the ability to do any uploads and carry on with editing or other daily life without constantly needing to interact with it.

Is anyone else experiencing this? And was anyone able to rectify this?