Struggling medical trainees pose a challenge to clinical teachers, since these learners warrant closer supervision that is time-consuming and competes with time spent on patient care. Clinical teachers’ perception that they are ill equipped to address learners’ difficulties efficiently may lead to delays or even lack of remediation for these learners. Because of the paucity of evidence to guide best practices in remediation, the best approach to guide clinical teachers in the field remains to be established. We aimed to present a synthetic review of the empirical evidence and theory that may guide clinical teachers in their daily task of supervising struggling learners, reviewing current knowledge on the challenges and solutions that have been identified and explored. A computerized literature search was performed using Medline, Embase, Education Resources Information Center, and Education Source, after which final articles were selected based on relevance. The literature reviewed provided best evidence for clinical teachers to address learners’ difficulties, which is presented in the order of the four steps inherent to the clinical approach: 1) detecting a problem based on a subjective impression, 2) gathering and documenting objective data, 3) assessing data to make a diagnosis, and 4) planning remediation. A synthesized classification of pedagogical diagnoses is also presented. This review provides an outline of practical recommendations regarding the supervision and management of struggling learners up to the remediation phase. Our findings suggest that future research and faculty development endeavors should aim to operationalize remediation strategies further in response to specific diagnoses, and to make these processes more accessible to clinical teachers in the field.