The paper “The Patient Experience in Ontario 2020: What Is Possible?” provides useful context setting, definitions that frame the essential principles of good relationships and challenges for outcomes by 2020 for the people of Ontario. The question – Is it ambitious enough to achieve a patient-centred healthcare system by 2020? Does it build on the deep strengths already evident in Ontario to achieve the outcomes essential to a thriving region? Will the challenges accelerate dramatically improved outcomes in better health, better care and lower costs? The risk of aiming too low is that it allows for an incremental, comfortable-for-us-in-healthcare pace when what is required is ambitious, disruptive moves. This commentary offers suggestions for Winning Conditions that build on those proposed and takes steps beyond – Winning Conditions 2.0 – to assure a health system the citizens of Ontario expect and deserve.