Millions of Canadians might lose their jobs to automation in the next decade. Hundreds of thousands of others could see their full-time positions replaced with short-term, temporary gigs. What will happen to the people currently holding these jobs? Will they end up cycling through unemployment benefits, drawing down their personal assets and surviving on social assistance? Will they have access to robust, effective training to re-skill and upgrade their skills for new opportunities? What if they require access to medicine or mental health services, or their ability to afford housing diminishes? How long will it take them to re-enter the labour market as new tasks and types of jobs emerge, and will their new roles make them part of the ever-expanding precariously employed workforce? These are vital questions that Canadian governments must start grappling with today. Autonomous vehicles are already on the road, robo-advisors are dispensing financial counsel and even lawyers and reporters are starting to see automation take over routine functions. The role of digital sharing economy platforms in creating micro-tasks that offer more supplemental income opportunities, but less permanence and security must also be considered as a key part of the technological wave disrupting labour patterns. This report argues that prevailing economic and labour market trends combined with emerging technological factors are creating a growing number of workers with little or no attachment to Canada’s social architecture. Absent transformational policy change to recognize the new world of work, Canada’s social policies and programs will prove woefully inadequate to sufficiently insure enough people to meet the challenges ahead.