Reflection in healthcare education is an emerging topic with many recently published studies and reviews. This current systematic review of reviews (umbrella review) of this field explores the following aspects: which definitions and models are currently in use; how reflection impacts design, evaluation, and assessment; and what future challenges must be addressed. Nineteen reviews satisfying the inclusion criteria were identified. Emerging themes include the following: reflection is currently regarded as self-reflection and critical reflection, and the epistemology-of-practice notion is less in tandem with the evidence-based medicine paradigm of modern science than expected. Reflective techniques that are recognised in multiple settings (e.g., summative, formative, group vs. individual) have been associated with learning, but assessment as a research topic, is associated with issues of validity, reliability, and reproducibility. Future challenges include the epistemology of reflection in healthcare education and the development of approaches for practising and assessing reflection without loss of theoretical background.