Motivational Interviewing (MI) has been labeled a “natural fit” for community corrections. Yet research-to-practice can frustrate both those who practice and those who study. This article offers qualitative examination of direct fieldwork for implementing training-of-trainer models in Motivational Interviewing, including lessons learned from over a decade of implementing large-scale MI projects across corrections. The authors finish with a look at the 2020 COVID-19 pandemic and how MI instruction and implementation has continued through multi-day web-training sessions and web courses.