The present invention is directed towards systems and methods for dynamically redirecting on a client communications of the client with a server to bypass an intermediary that is determined to be unavailable for such communications. An acceleration program on the client establishes a transport layer connection between the client and server, and intercepts communications of the client to the server. The transport layer connection may be established via an intermediary, such as a gateway, proxy or appliance. If the client-side acceleration program determines the intermediary is not available for communicating by the client to the server, the acceleration program automatically establishes a second transport layer connection to the server in order to bypass the intermediary. The acceleration program then transmits the intercepted communications of the client via the second transport layer connection to the server. The acceleration program may automatically redirect intercepted communications of the client to the server transparently to any user or application of the client.