A connection method and a management server are provided. Each electronic apparatus detects connection behavior supported by a network, where the electronic apparatus is located, through the management server and accordingly generates a corresponding connection profile and stores it to the management server. The management server reads two connection profiles corresponding to two electronic apparatuses when the management server receives a connection request desired to connect from one of the electronic apparatuses to another one, and dynamically adjusts a plurality of connection detection procedures based on a connection success/failure record. The management server tests the connection detection procedures to determine whether a connection can be established between the two electronic apparatuses so as to obtain a session profile for establishing the connection.