Ecologists have long since realized that postage size disconnected protected areas are not likely to conserve the world’s biodiversity.  There is much literature about doing conservation at landscape and seascape scales, but what does it really mean to achieve conservation at scale? The importance of conservation at scale and conservation of water is intensified given the changing climate. We examine progress toward the vision laid out 20 years ago of “An interconnected system of wild lands and waters stretching from Yellowstone to Yukon, harmonizing the needs of people with those of nature”.  We quantify progress of increased protection and conservation progress.  Despite clear and significant progress, enormous hurdles remain including skepticism, politics, and increased human activities and developments increasing at exponential pace in the region.  We focus on next steps for better protecting headwaters and what will be required to tackle compounding challenges into the future.