Techniques for detecting exfiltration content are described herein. According to one embodiment, a malicious content suspect is executed and a packet inspection of outbound network traffic is performed by a packet inspector running within the virtual machine. Occurring before the outbound network traffic leaving the virtual machine, the packet inspector determines whether a portion of outbound network traffic matches one or more portions of predetermined network traffic patterns or signatures. If so, a determination is made whether the outbound network traffic includes at least one environmental property of the virtual machine that is unique or almost unique to the virtual machine. If so, migration of the outbound network traffic outside of the virtual machine is precluded and an alert is transmitted. The alert includes the malicious content suspect that is attempting to perform an exfiltration of data.