[pyuser583]

Known-plaintext attacks aside, if you're going to compress text, it must be done before encryption.

I don't know if compression offers much protection against plaintext attacks.

This also makes me wonder how helpful AI is in such situations. AI is essential an extremely effective, lossy, compression algorithm.

[hcs]

Compression + encryption can be dangerous if the compression rate is exposed somehow (between messages or within packets of a message).

> we show that it is possible to identify the phrases spoken within encrypted VoIP calls when the audio is encoded using variable bit rate codecs

https://crypto.stackexchange.com/a/2188

See also https://breachattack.com/ when the plaintext is partially attacker-controlled.

[bee_rider]

If nothing else it would make a great twist in a fiction setting.

These paraphrasing instructions could be followed. But the paraphrasing could be done using some LLM. A sufficiently advanced adversary manages to invert the model somehow, and as a result can get the original plain text out of the paraphrased message, which lets them do a known-plaintext attack, get the key, and use it on other messages.

Sort of technobabble (is the idea of inverting an LLM nonsense?) but fun.