A communication connection system, a communication connection method, and a communication connection program is capable of establishing push-type communication by a connection request from a server side, rather than a client side, in communication between terminals or a terminal and a server. A polling server 50 periodically conducts polling to a connection server 100 to check if the connection server 100 has received connection request data. The polling server 50 transmits the connection request data 10 to a user terminal 10 when the connection server 100 determines that the connection server 100 has received the connection request data from a support terminal 150. The user terminal 10 connects with the support terminal 150 through the polling server 50 and the connection server 100 by a predetermined communication application regardless of input by a user when the user terminal 10 receives the connection request data.