The Palestinian information technology (IT) sector is growing. Meanwhile, an ongoing out-migration of IT professionals and graduates is taking place. Drawing on group, pair and individual interviews, as well as fieldwork observations, this paper investigates highly skilled IT students' intentions to stay in or to leave the West Bank. In particular, it examines their transition from university to employment or further education, including professional opportunities and factors affecting migratory and stay decisions. This paper shows how physical, legal, bureaucratic, professional, educational, cultural and personal factors shape professional plans and career trajectories. Particular attention is paid to the Israeli occupation and gender expectations. The students' mobility is facilitated by completed degrees and diplomas, acquired skills and scholarships, all of which are potential tools to overcome restrictions. However, this study reveals a clash between aspirations and reality, which often results in limited freedoms. We argue that a student's relative (un)freedom contributes to (im)mobile transitions from university to employment or further education, where migration could be a way to obtain freedoms or to escape the lack thereof.