A Voice-over-Internet-Protocol (VoIP) system includes clients that make management connections to an external manager server using web-browsing protocols. A discovery process tests a variety of transport methods by sending packets using different protocols to several ports of the external manager. Some packets may be blocked by firewalls, while other packets are allowed to pass through. Successful packet replies indicate transport capabilities of the client. When a client makes a VoIP call to another client, the external manager compares transport capabilities of the two clients and selects a transport capability that is common to both clients. Transport methods include direct client-to-client connections using TCP or UDP to an arbitrary port or well-known port 80 or 443, and indirect using a voice-proxy server that each client connects to using web standards such as HTTP or SSL. When a client can make only outgoing connections, that client initiates the connection.