A messaging server establishes a video chat between first and second endpoints through a first and second router. In parallel, the messaging server transmits instructions to the first endpoint causing the first endpoint to transmit packets through a plurality of ports of the first router to a designated port of the second router. In addition, the messaging server transmits instructions to the second endpoint causing the second endpoint to transmit packets through a plurality of ports of the second router to a corresponding plurality of ports of the first router. A P2P connection is established between the first and second endpoints in response to a first port of the plurality of ports of the first router receiving a data packet from the designated port of the second router. The video chat is seamlessly transferred from the connection established through the messaging server to the established P2P connection.