COVID-19 tested insurance digital strategists' ability to think in long- and short-term dimensions at the same time. Insurers, accustomed to the "inertia of the ordinary," suddenly had to abandon the linear swim lanes of traditional transformation roadmaps to meet fast-changing needs. How did insurance digital strategists and their tech partners revamp their pre-COVID-19 thinking into new approaches to their tactics, strategies, and visions? This report, the roadmap chapter of the digital insurance strategy playbook, examines how insurers adapted their planning processes as a result of COVID-19 and why many of those changes will stick.