Even strong encryption systems can be undermined by poor implementation, weak configurations, or direct cryptographic attacks—and recognizing the signs is vital. In this episode, we cover indicators of cryptographic compromise, including protocol downgrade attacks, hash collisions, weak cipher suites, and the use of deprecated algorithms like MD5 or SHA-1. Attackers may force systems to negotiate older, insecure protocols (e.g., SSL 2.0) or exploit hash collisions to forge digital signatures and bypass validation. Telltale signs include unexpected changes in protocol negotiation, failed certificate validation, inconsistent signature behavior, or audit logs showing unapproved algorithm use. We also explain how improperly stored keys, missing certificate chains, or repeated handshake failures can signal deeper cryptographic issues. Proactive defenses include enforcing cryptographic hygiene through configuration audits, certificate monitoring, and regular algorithm reviews. Cryptographic strength isn't just about key length—it's about knowing what your systems are doing, and ensuring they’re doing it securely.