I had the same issue as OP. I tried 3 times - no luck. After that I did a factory reset on Shield and tried 5 more times - no luck. All this time the remote was charging. I disconnected the cable and after second try it was successful.
I just updated to the latest 5.0 firmware for the first gen Shield TV and the remote has an update...but won't update. Any ideas on how to fix that?
This also happened to me when updating my accessories.
The controller had no issues, but the remote update failed with the exact same error message. I just ran the update again and it worked.
I would keep trying the update.
I have the same problem since I updated to the latest Shield TV Jan/2017 update. I was able to update the NVIDIA game controller without issues, but the NVIDIA remote refuses to update. Anyone have a solution for this?
I would try both, when it's connected via USB and when it's not connected. You should also make sure it's fully charged.
Mine did that. I had it plugged in charging (to a wall charger), it failed once while i was holding it, I left it on the coffee table and tried again and it worked and then it worked.
I rebooted my shield and it worked the 3rd or 4th try after that
I just tried to update and got the error, but now my remote won't work... Update: had to repair the remote and ran the update again and it worked.
Just updated the Shield to 5.1.1, but still unable to update the remote!
Unable to update the following accessories Shield Remote 1: Accessory disconnected. Connect accessory and try again
Here's what I just did after multiple failed attempts. Fully charge it, Unplug it, and set it on a table close to the Shield. Then use the controller to initiate the remote update. Don't touch it until the update completes.
Same here, I had to try it a few times before it worked.