Phenomenon: Choosing a medical specialty is a critical decision that significantly impacts medical students’ future career. Understanding the factors influencing this decision-making process is important for medical educators, policymakers, and healthcare providers to develop effective strategies that support and guide students in making informed decisions. Approach: We distributed an online self-administered questionnaire to clinical-year medical students (Years 4 to 6) and interns from all medical faculties in Jordan. The questionnaire gathered demographic information, specialty preferences, and factors influencing specialty decision-making. We analyzed the data using descriptive statistics and logistic regression. Findings: 1805 participants completed the questionnaire (51.7% women). General surgery was the most preferred specialty among both genders, followed by internal medicine. Women significantly preferred family medicine, pediatrics, obstetrics and gynecology, and dermatology, whereas men significantly preferred urology, orthopedic surgery, neurosurgery, general surgery, and internal medicine. The factors that most strongly influenced respondents’ specialty preferences were the specialty’s perceived stress levels and working hours, whereas the least influential factors were the specialty’s perceived prestige and role models in the specialty. Women’s specialty preferences were significantly more influenced by their family than men’s. Men were substantially more influenced by specialties’ perceived action-orientation and stress levels than women. Insights: Gender significantly influences medical trainees’ specialty preferences in Jordan. Women tended to prefer specialties that provided greater work-life balance, such as family medicine, pediatrics, obstetrics and gynecology, and dermatology, while men were more drawn toward competitive and profitable surgical specialties like orthopedic surgery, neurosurgery, urology, and general surgery. Additionally, family had a stronger influence on women’s decisions, likely due to cultural and social expectations prioritizing marriage and family for women. Career counseling and mentorship programs are needed to provide guidance, support, and networking opportunities that can help women overcome barriers and biases that may hinder their career advancement.