The use of technology and learner autonomy are two key issues in English for Specific Purposes (ESP) programs. This study aimed to investigate Iranian medical students' readiness to do ESP tasks based on five situations and discover their reasons for choosing each of the situations. Two of the situations (1 and 2) embodied a conventional autonomous learning process, two (3 and 4) represented a technology-mediated autonomous learning process, and one (5) was based on a self-study method. Data were collected by means of a questionnaire and semi-structured interviews. The results showed that the students' choices of the situations in order of priority were situation 2, situation 3, situation 1, situation 5, and situation 4. The themes emerging from the content analysis of the students' reasons for choosing each of the situations were: Situation 1: concentration, individuality gains, professor, group work problems, and learning gains; Situation 2: professor, information exchange, learning gains, personal contact gains, motivation, confidence, discipline, and Internet problems; Situation 3: professor, information exchange, learning gains, time management, accessibility, face-to-face contact demerits, and discipline; Situation 4: stress free, time and language problems; and Situation 5: concentration, individuality gains, time, and university problems. The study concludes that the majority of the students have a low level of readiness for technology-mediated autonomous learning situations. It suggests that the students' autonomy be promoted through raising their awareness about, motivation for and confidence in using technology for educational purposes and creating incentives for ESP teachers to foster technology-mediated autonomous learning.