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The sections "How are browsers hostile to cryptography?", "What systems programming functionality does Javascript lack?", "What else is the Javascript runtime lacking for crypto implementors" cover issues you would encounter with browser extension cryto.

I didn't realize extensions were largely javascript. Thanks for the pointers.

Ah yeah. I believe the usual terminology is such that "extensions" are javascript and "addons" are something native. You could probably do cryto well with an addon.. to the extent that it is possible to do an addon at all properly (honestly I have no idea there).

Presuming you're securing against gmail monitoring, Google in this case would be the eavesdropper/attacker.

Google controls the key/cert that allows for Chrome extension updating...

I think you could at least have it implemented in NaCl in Chrome, if the Javascript versions fail.