I had no luck updating a new Kickr core from android… borrowed an iPhone and it worked first time. I think it’s a common problem and solution
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Yeah I’ve been on hold with them for 25 minutes and then it just alerted me they’re now closed. 0/2 Wahoo. 
I forgot if you can see firmware version in the app, if you can, what version firmware is on your Core?
Here are the Core firmware versions:
I had my Kickr 2017 on older firmware more than a few times, and once for over 6 months. It really didn’t make a difference.
Yeah, I’m on .10, and really want the .11 features (cadence, multipoint pairing.)
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When I had this issue back in Oct 2018 I contacted Wahoo support and they said it was an issue with all Pixel 2 phones. They said it would be fixed in a future app update but that hasn’t panned out. I have never had a successful update with my Pixel 2 phone. I almost resorted to bring it to my LBS and using one of their iPads before remembering my Amazon Fire tablet, which worked.
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Lovely. Well, thanks for letting me know. Guess I’ll take it to a friend’s or something (no other devices).
Not sure this will help…but I ran into the same issue and followed the directions to restart the Kickr and the Wahoo Fitness app but that didn’t work. So then finally I shut down the TrainerRoad application which had a paired Bluetooth connection to the Kickr and then suddenly the flash update completed successfully, Your mileage may vary. 
I always have issues updating the firmware on my kickr core. Turning off all other Bluetooth devices, trying from different positions and just keep re-trying, it always works eventually. Sometimes takes a few tries, last time took like 20…yea it’s shit.
I just tried this am after reading this thread… failed a bunch of times, eventually worked after turning off BT on all other devices, rebooting my iPhone, power cycling the Kickr Core. No idea what the trick was (though rebooting iPhone was last step before it worked, but even then took 2 or 3 fails before working).
Be careful when updating Kickr Core firmware not to go higher than v1.0.13. If you go to the latest firmware, the spin up calibration doesn’t work on TR. I raised this with TR support and the advice was to revert back to an old version.