There was - I "clicked to fix" and it came back red afterwards, so I opened up chrome on my laptop (was using Safari for the click to fix step) and actively asked for the latest minor update there, clicked back over to safari and the check was now green. This seems to have let me get past the login context cancelled error so that's good, now seeing the channels again and they can be tuned!
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No. The Chrome/Chromium used for TV Everywhere is on the DVR; whichever browser you personally use to view the DVR web UI isn't necessarily connected in any way.
Ah, so that must be updating it on the shield then?
Correct.