A first device initiates a handshake message exchange with a second device according to a security protocol. The first device determines that an application datagram is to be transmitted according to a first transport protocol that limits a size of a datagram based on a defined size. The first device also determines that an application datagram size is larger than the defined size. The first device fragments the application datagram if the application datagram size is larger than the defined size and secures the application datagram with the security protocol. The first device also encapsulates the application datagram fragments in handshake messages, wherein an encapsulated application datagram fragment is transmitted from the first device to the second device in a first security protocol record. The first device may also transmit, to the second device, another application datagram secured with the security protocol.