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I bought this USB-C extension cable, and learned that it only works for USB debugging on Android when the Pixel's stock cable is plugged in the "correct" way. There's even a little label on the end of the extension cord telling you to reverse the connection if it doesn't work. /facepalm

https://smile.amazon.com/gp/product/B071DMMW4J

I've got a Nexus 5x that now only charges if my USB A -> C cables are oriented properly. When it was new, it would charge in both directions as expected.

Yes. Early USB-C controllers had notorious issues with CC pins getting fried out by short-to-Vbus events, which could make the port work only in one orientation (or not work at all if you're unlucky enough to fry both CC pins).

Perhaps not, I suspect that the pins are probably normally tied together. That it's possible, and some of the failure modes are _weird_ is a bit frustrating.