For the last ten years, the idea of "Digital Transformation" has animated business and technology circles around the world. The notion is simple- replacing analog and inefficient products and processes with digital products and processes will usher in a new era of agility, performance, and engagement. The idea is a powerful one and has taken root everywhere it has gone. Of course, as with all such grand notions, execution matters and on that score, the jury is still out. I argue that the reason that a vast divergence exists between idea and execution is the matter of context. Put simply, specifics matter and static, parachutist solutions don't meet the needs of complex organizations, whether SMBs or Enterprises. For the sake of phraseology, we'll coin the term "Agile Context" to point us on the right path.