Women in the sex trade encounter significant challenges in obtaining reproductive healthcare. Reports of reproductive healthcare for women in the sex trade center on the prevention and termination of pregnancies, yet most women in the sex trade globally experience full term pregnancies and bear children. This study aimed to explore barriers and enabling factors to providing reproductive healthcare for women in the sex trade in Israel. We conducted a qualitative study utilizing a grounded theory method. Data were collected through semi-structured interviews, conducted between June 2021 and July 2022. Interviews were conducted with practitioners in healthcare settings (n = 20), practitioners in social services settings (n = 15), and women in the sex trade who received reproductive health care-related medical services (n = 13) in Israel. The interviews were audiotaped, transcribed, and thematically analyzed. The findings indicated a multilayered structure of healthcare system-related factors and women-related factors. Stigma was noted as a multidimensional barrier, reflected in service providers' attitude towards women in the sex trade, impairing the patient-provider relationship and impeding women's help-seeking. However, the creation of a relationship of trust between the women and healthcare providers enabled better health outcomes. Based on the findings, we propose recommendations for designing and implementing reproductive healthcare services for women in the sex trade. The recommendations offer to (a) include women with lived experiences in planning and providing reproductive healthcare services, (b) adopt a trauma-informed approach, (c) emphasize nonjudgmental care, (d) train healthcare providers to reduce stigma and bias, and (e) enhance the affordability of health services for women experiencing marginalization.