In some embodiments, a computer-implemented method for an automated proxying TCP fingerprints comprises: receiving, at a proxy server, a request from a source host, to establish a first communications connection between the source host and a destination host; establishing, by the proxy server, a second communications connection between the source host and the proxy server; determining a plurality of fingerprint values specific to the source host; establishing by the proxy server, using at least the plurality of fingerprint values specific to the source host, a third communications connection between the proxy server and the destination host; facilitating, by the proxy server, communications between the source host and proxy server via the second communications connection and between the proxy server and the destination host via the third communications connection.