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Thanks @edb I tried it today and got it working on Chromium on Fedora so I'll count that as a win :)
I did actually try your suggestion of pairing the watch with the bluetooth manager before I attempted to upload the firmware, so maybe that helped. I'm not sure what fixed it but I appreciate your suggestion anyway.
Thanks again :)
Updating firmware worked fine on my chromium on Ubuntu after enabling both chrome flags.
Sometimes I do need to pair the watch first in the bluethooth manager before it wants to connect in chromium.