A communication system and a security assurance device are proposed, which are capable of assuring that a target party for communication is implementing security countermeasures. A server 3 transmits information 104 necessary for AC issuance to a security assurance authority 2. The security assurance authority 2 verifies the security of the server 3 during communication based upon this information necessary for AC issuance 104. And, when the security of the server 3 during communication is confirmed, the security assurance authority 2 issues an AC 105 which proves the security of the server 3 during communication, and transmits it to the server 3. Upon receipt of this AC 105, the server 3 transmits the AC 105 to a client 4, according to a connection request from the client 4. And, upon receipt of this AC 105, the client 4 verifies the security during communication of the server 3, based upon the AC 105.