Natural Language Understanding and Word Sense Disambiguation remains one of the prevailing challenges for both conversational and written word. Natural language understanding attempts to untangle the 'hot mess' of words between more structured data in content, but the challenge is not trivial, since there is so much polysemy in language. Some recent developments in machine learning have seen significant leaps forward in understanding more clearly the context (and therefore user intent and informational need at time of query). Here we will explore these developments, and some of their implementations and seek to understand what this means for search strategists and the brands they support both now and into the future.