A graceful conversion of a security to a non-security transparent proxy is performed. A security transparent proxy is an intermediary between two end devices, with an established secure connection with each end device using different security keys. In response to a policy decision or other stimulus, the security transparent proxy is gracefully converted to a non-security transparent proxy such that it can forward, without decrypting and encrypting, the information received from a first endpoint on the first connection therewith to the second endpoint on the second connection therewith. This conversion is “graceful” in that it does not drop either of the two original sessions. In one embodiment, this graceful conversion is accomplished by triggering a key renegotiation on both of the two sessions such that the two connections will use the same encryption key.