I had the same problem recently with my OBIEXTRAS subscription. I opened a support ticket and emailed Obi Support. Several days later I tried to upload again and it still failed. Then a few days after that I got an email from Obi telling me to try again and it worked. But then, a few days later my Obi 200 would not work. It would not connect with GV even though my GV account was fine. So I replaced the Obi 200 with another one and all worked. Coincidence? Maybe. I've opened a ticket to have them transfer the remainder of my OBIEXTRAS subscription to the replaced device. Also asking to have the defective Obi 200 replaced (it's under extended warranty).
It seems to take Obi support a long time to respond and fix problems.