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Abstract The chapter discusses key questions that shaped the practice of monitoring, evaluation, and learning in the Global South after the COVID-19 pandemic, offering alternative lines of thought likely to be transformed into practical criteria. Diverse issues are examined and discussed, both as guiding topics to tailor evaluation practice to the specific coexisting realities of the Global South and as subjects requiring further reflection: How do we deal with uncertainty? How do we measure (unexpected) change in volatile contexts? What do donors mean when they ask for the effects of the intervention? How do we respond to increasing pressure for soft data amid rising insecurity for human rights defenders? How do we nurture transparency platforms without exposing front-line defenders? How do we ensure efficiency while guaranteeing a rights-based approach? How do we amplify views and voices? How do we avoid methodological fundamentalism? How—and why—should we adopt a feminist approach in evaluation, even when not required? How will program evaluation look in the postpandemic era? And finally, how do we go beyond donors’ requirements? The reflections focus on three main challenges for evaluation in the Global South: the need to move from participation to collaboration, promoting collective empowering processes; the importance of preserving people’s integrity over privileging methodological aspects; and the need to progress from collecting lessons, learnings, and experiences from the Global South to supporting recognition and visibility of epistemologies born in and shaped by the region.