One of the difficulties of deploying and using cryptography is it must have no mistakes in the entire "stack", no errors committed by any user. An artificial intelligence agent that watches over you could help, being able to reason about situations it has not encountered before. Preventing user error seems especially hard with the difficulties of HCI compounded by the non-intuitiveness of cryptography and computer security.
"Describe your problem."
"You're doing it wrong."
"You look like an attacker."
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