Attackers can freely exfiltrate confidential information all while under the guise of ordinary web traffic. A remedy for businesses concerned about these risks is to decrypt the communication to inspect the traffic, then block it if it presents a risk to the organization. However, these solutions can be challenging to implement. Existing infrastructure, privacy and legal concerns, latency, and differing monitoring tool requirements are a few of the obstacles facing organizations wishing to monitor encrypted traffic. TLS decryption projects can be successful with proper scope definition, an understanding of the architectural challenges presented by decryption, and the options available for overcoming those obstacles.