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When I experience problems trying to upload anything, it is usually caused by 1 of 3 things… #1 the file I am trying to upload is too big, my Internet connection gets temporarily cut (causing the upload to fail) or an anti-virus, security, firewall or pop-up blocker software is causing the issue.
Try this for testing purposes…
Create a small Word or Text file with a few letters inside the file like, “test”, then save. Upload that super tiny file to Gmail. Then send it to someone or another email account you own.
Does it upload? If Yes, try to upload a larger file. A larger file could be a pic you took on your cell phone or if your PC has a webcam on it. Take the pic on medium quality settings.
Were you able to upload any of these files I mentioned during your testing?