A recurring theme is the security benefits of cascading two or more different ciphers. The idea is to enhance security, especially if one of the ciphers is later compromised. Intuitively (see below), cascading ciphers with independently chosen keys should result in a cipher at least as strong as the strongest one used. However, this is not always the case. A paper by Maurer and Massey (free download: https://link.springer.com/article/10.1007/BF02620231) provides a counterexample to this "folk-theorem," (their words) by claiming to demonstrate how two ciphers, C1 and C2, can become less secure when cascaded (see page 4). The paper further argues that the cascade's security is only guaranteed to be as strong as the first cipher and argues that previous proves to the contrary didn't account for attacks exploiting plaintext statistics.
Here's my counter-argument to their counter-example: Critically examining the example from the paper, neither C1 nor C2 could be considered secure ciphers. The counterexample demonstrates that C1 maps 'A' and 'B' to the same values regardless of the key, rendering it 'completely insecure' (in the paper's own words) for plaintext consisting solely of 'A's and 'B's. Similarly, C2 has the same issue for 'C' and 'D'. Given the inherent weaknesses of both ciphers, it is unsurprising that their combination is also insecure. The folk theorem (and its intuition) demands that at least one of the ciphers is secure which wasn't the case in the counter-example.
Therefore, if we impose stronger security requirements on the ciphers, the folk theorem might still hold, irrespective of the ciphers' order in the cascade.
My intuition supporting the folk theorem, regardless of which cipher is the secure is as follows - let's let C1 be the first (inner) cipher and C2 the outer cipher.
Scenario 1: C1 (inner) is Secure, C2 is insecure/less secure:
If C1 is secure and C2 is less secure, the resulting cascade should still be secure because an attacker could theoretically apply C2 themselves. If merely applying C2 (with a random key) to the ciphertext output of C1, helped break C1, it would imply that C1 was not secure to begin with.
Scenario 2: C2 is Secure, C1 is Less Secure:
If C2 is secure and C1 is less secure, the cascade should remain secure because the final encryption is done by C2. If C1 altered the plaintext in a way that it was no longer possible to encrypt it securely by C2, with a random key, then C2 was not truly secure. It seems a secure cipher should withstand any input of the user's choosing.
Applying this to the counterexample in the paper, the reason the cascade isn't secure is that neither C1 nor C2 meets the security assumptions. Thus, if at least one of the cipher individually satisfies strong security criteria, the folk theorem should hold.