Cybercriminals persistently challenge the security of organizations through the rapid implementation of diverse attack methodologies, state of the art malware, and innovative evasion techniques. In response organizations deploy and rely on multiple layers of diverse security technologies. This talk examines the “kill chain” and the measured effectiveness of typical defense technologies such as Next Generation Firewalls, Intrusion Prevention Systems IPS, Antivirus/Malware Detection, and browsers internal protection. Empirical data on the effectiveness of security products derived from NSS Labs harsh real world testing is presented together with a live demonstration of successful evasion of malware detection. We find a considerable gap of protection levels within/and across different security product groups. The presentation will be backed up with a paper to be made available to attendees.