Puerto Rican English teachers are included in a difficult recruitment category because a shortage amount of them reached a university degree in this area every year. The primary purpose of this qualitative, multiple case study was to explore how Elementary English teachers perceived their first experience as professional versus the knowledge they acquired in their bachelor's degree. Likewise, this study tried to identify those college courses that made easier their first experience of teaching at the Department of Education of Puerto Rico and how the universities reduce the dilemma of transition between the theory and practice in these professionals. Five new English teachers recruited in Puerto Rico's public schools with an experience of less than three years in this area participated in this research. Data were collected through two independent semi structured interviews, a review of documents related to school and universities, and the investigator field notes. Analysis of the data suggested that both, Puerto Rico's universities and the Department of Education need to keep up the most effective communication in order to bring these professionals the skills and knowledge they need to master as Elementary English teachers in public schools in Puerto Rico as well as they feel reliable during their transition between formal studies and job experience, and decide to keep their profession.