Context matters in implementation. The Lenawee ISD (LISD) in Michigan navigated implementation through major changes in its school district’s administration and the COVID-19 pandemic. The district highlighted in the impact story experienced leadership change in the District Superintendent position and three school principal positions. The district and LISD credit the sustained use of MTSS to the accomplished system work. The initial cohort of districts reported their ability to respond quickly and proactively to the COVID-19 pandemic due to their teaming and systems being in place. As the LISD implementation team reflects on their MTSS implementation journey to date, several key learnings are generated.