Systems and methods to rotate security assets used to for secure communications are disclosed. The system includes initiating a communication session between two servers. Additionally, a server provides a first version of a first certificate to another server. The first version of the first certificate has identifying information including a first public key. The server receives a second certificate. The server determines that the second certificate is trusted by determining that the second certificate has identifying information matching the identifying information of the first version of the first certificate. In response to determining that the second certificate is trusted, the server encrypts the first public key. The server provides the encrypted first public key to the other server. The server then receives a verification of decryption of the encrypted first public key.