The system and method detect and properly handle a glare condition in a SIP communication session. A glare condition is where a communication device has two concurrent outstanding requests (typically an incoming and an outgoing request that have not be acknowledged) and needs to process one of the requests before processing the other request. To detect a glare condition, the system and method identify that an out-of-dialog SIP request is received while an outgoing SIP request is pending. In response to detecting the glare condition, a glare algorithm is initiated. The glare algorithm ensures that outstanding requests will be handled in a timely manner.