The transition from undergraduate medical education (UME) to graduate medical education (GME) is a pivotal milestone for medical professionals, marked by both excitement and stress. Effective onboarding and orientation are crucial to easing this transition, addressing the logistical, educational, and social aspects necessary for new residents. Comprehensive orientation programs familiarize residents with institutional and programmatic policies, diversity and cultural humility, structural competency training, and opportunities for new residents to build bonds and develop their community. Residency programs must design robust orientations that include experiential learning and hands-on sessions, given the extensive content covered. Early introduction of mentors, regular feedback, and tailored needs assessments allow for personalized guidance and can help residents navigate their evolving responsibilities, mitigate stress, and promote well-being and professional growth. Emphasizing wellness and self-care from the outset helps prevent burnout and fosters a healthy work–life integration. Regular evaluations and feedback-driven improvements ensure the onboarding process meets evolving needs. Effective onboarding and orientation programs lay the foundation for resident success, enhancing their ability to provide high-quality patient care and positively impacting overall residency experience and outcomes. Through careful planning, execution, and continuous refinement, program directors can significantly improve outcomes for residents, patients, and the program.