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Strong encryption has properties that make "known plaintext" attacks impossible. You should not be able to tell the message from pure randomness. Breaking End-to-End-Encryption is not impossible but rather far fetched. If they read Snapchat, my bets would not be on broken crypto, but rather a lack thereof.

I don't see any use for hashing here, and encrypted messages have padding (otherwise you could trivially decrypt simple messages like yes/no)

A more serious problem with the story is if they had any kind of advanced (or magical) brute force or mathematical path against some standard encryption scheme - they would not waste that major secret on some random 18yo joker.

(Although in the background, fuckups are always possible and they did send a fighter jet initially so there was some pressure to follow through. Still not enough to risk a major secret.)

I don’t know. Without even going in normal standard crypto, if you XOR a few words with a random initialisation vector, is it possible to flag those messages?