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Systematic methodology for identifying and exploiting cryptographic implementation weaknesses in real-world applications. Covers padding oracle attacks against CBC-mode ciphers with PKCS7 padding (Vaudenay's original attack through modern padbuster automation), ECB mode exploitation including block cut-and-paste and byte-at-a-time decryption, hash length extension attacks against SHA1/SHA256/MD5-based MACs using HashPump, RSA vulnerabilities including small public exponent, common modulus, Bleichenbacher PKCS1v1.5 padding oracle, and Coppersmith's method for partial key recovery. Addresses weak PRNG exploitation targeting time-seeded generators and Mersenne Twister MT19937 state recovery from observed outputs, timing side-channel attacks against comparison operations, nonce reuse in AES-GCM leading to authentication key recovery, and key derivation weaknesses including insufficient iteration counts and missing salts. Primary tooling includes padbuster, RsaCtfTool, hashpump, and PyCryptodome for building custo