Existing models for information security are at a breaking point. Static and rigid security infrastructure inhibits business change and opportunities. Consumerization, Cloud computing and collaboration challenge our preconceived binary notions of "us" versus "them". The future of information security must become contextual and adaptive to changes in business requirements and targeted threats. Richer, real-time context such as trust, identity and content-awareness at the point of a security decision will provide the foundation for more accurate and timely security decisions.