The disclosed computer-implemented method may include (1) detecting an online communication session established between a plurality of computing devices, (2) identifying at least one application involved in the online communication session established between the plurality of computing devices, (3) determining a security mode for a security proxy that inspects the online communication session based at least in part on the application involved in the online communication session, and then (4) configuring the security proxy to inspect the online communication session in accordance with the determined security mode. Various other systems, methods, and apparatuses are also disclosed.