Examining teachers’ motivation to stay in the profession may help sustain and expand the teaching workforce in Timor-Leste. Using quantitative methodologies, the study explored the factors that influence teachers’ motivation to stay in their teaching careers. Descriptive statistics revealed that many Timorese teacher respondents are very highly motivated to remain serving as teachers. They also view all core and contributing motivational factors positively (i.e., ‘sense of purpose and fulfillment’, ‘teaching as interest and passion’, ‘sense of growth and development’, ‘sense of being respected and valued’, ‘teacher well-being’, ‘school environment’, ‘salary, incentives and benefits’, and ‘government laws and policies’). Inferential statistics showed that the length of teaching is positively associated, albeit to a very weak extent, with teacher respondents’ motivation levels. Hierarchical regression analysis, on the other hand, identified a combination of factors and variables that predict teacher respondents’ motivation to continue teaching, including the factor ‘sense of being respected and valued’, length of teaching, participation in professional learning communities and/or networks, kindergarten as a grade level taught, and gender. Several policy recommendations were also proposed based on the results of the study.