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This multiple case study examined the impact of COVID-19 on twelve teachers’ decisions to remain, re-enter, or leave the field of music teaching. This two-year study is a subset of a six-year study about music teacher identity and resilience. We followed twelve participants from institutions in three regions of the USA: southeastern, southwestern, and western. Primary data were two semi-structured interviews per participant, a year apart. We reference back to previously collected data: music teacher philosophy statements, background surveys, and yearly interviews. While all participants considered leaving the profession during COVID-19, we present samples of within-case analysis, exploring why some exited the teaching profession or taught during the pandemic, followed by a cross-case analysis and implications.