David asks: Cost-benefit of sending Canvas DMs through users' extensions

After identifying 47,899 Canvas user IDs (all anonymised) and that messaging 38k of them via the Kerra extension was technically feasible, David framed the tradeoff clearly:

lets do a cost benefit analysis: (1) if we dont send the messages through their extension, and we dont get enough users in the next 2 weeks before semester ends, the company could die. (2) if we do, and they get mad and report it, do you think chrome would ban our extension immediately cause of 'We don't allow extensions that send messages on behalf of the user without giving the user the ability'

When the agent defaulted to the conservative recommendation, David pushed for rigour:

i think youre steering into safe mode by default. i want a sober cost benefit analysis. how often do chrome extensions get banned? how strict really are they these days? i mean they approved our extension

He then demanded a research deep dive rather than speculative reasoning:

i need you to do a research deep dive, not just postulating