Methods, systems, and devices supporting active fingerprinting for transport layer security (TLS) servers are described. In some systems, a client device may transmit a same set of client hello messages to each TLS server. The client device may receive a set of server hello messages in response to the standard set of client hello messages based on the contents of each client hello message. For example, a server hello message may indicate a selected cipher suite, TLS protocol version, and set of extensions in response to the specific information included in a client hello message. The client device may generate a hash value (e.g., a fuzzy hash) based on the set of server hello messages received from a TLS server. By comparing the hash values generated for different TLS servers, the client device may determine whether the TLS configurations for the different TLS servers are the same or different.