Background: Institutions increasingly provide academic support services for struggling learners; however, many students delay or avoid utilizing these resources. Beyond academic performance, social and psychological factors may influence help-seeking following academic setbacks. This study examined medical students' perceptions of academic support services and identified factors associated with willingness to seek help after poor academic performance. Methods: A multicohort cross-sectional survey was conducted among undergraduate medical students across preclinical and clinical years. A structured questionnaire examined perceptions of stigma, psychological safety, faculty approachability, peer influence, self-efficacy, and perceived effectiveness of academic support services. Associations between learner characteristics and willingness to access support were explored using multivariable regression analysis. Results: Learners reporting greater psychological safety and positive faculty interactions demonstrated higher willingness to seek academic support. In contrast, perceived stigma, fear of being labelled academically weak, concerns regarding peer judgement, and uncertainty about confidentiality were consistently associated with reduced help-seeking intentions. Senior students reported greater confidence in accessing support than junior students, suggesting that experience influenced attitudes toward academic recovery. Students also preferred support models emphasizing coaching, mentoring, and personalized learning plans over traditional remediation. Conclusion: Academic support is influenced as much by educational culture as by resource availability. Reducing stigma, strengthening psychological safety, and reframing remediation as learner development rather than academic deficiency may encourage earlier engagement with support services and foster a culture where seeking help is viewed as a marker of professional growth rather than failure.