This thesis explores the Transport Layer Security (TLS) protocol, a widely-used cryptographic protocol designed for secure communication between two parties by exchanging parameters such as cipher suites, keys, and certificates. Originally introduced as SSL 2.0 in 1995, the protocol has evolved to address emerging vulnerabilities, culminating in the current version, TLS 1.3, released in 2018. Despite these advancements, TLS remains susceptible to vulnerabilities due to specific implementations or misconfigurations. Existing tools, such as Qualys' SSL Server Test, TLSAssistant, and TLSAttacker, can assess a host's TLS security at a specific point in time, but lack the capability for continuous monitoring to detect changes that may expose systems to attacks.