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This question boils down to, "Are there known-plaintext attacks against AES-256-CBC?" The answer is: No, no such attacks better than brute force are known. This would constitute a catastrophic break in AES-256-CBC, and any cipher broken in such a way would be abandoned rapidly.


Some brief thoughts: Shared secret Generation: $$s=E_a(B)=E_b(A)$$ The shared secret is generated by encrypting the other users public key with your private key. This is effectively an ECDH step, which is very reasonable, and one of the key aims of C25519$^{[1]}$. Key Generation: $$s_0=\mathrm{SHA256}(s); s_i=\mathrm{SHA256}(s_{i-1})$$ First, using the ...

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