Despite the growing demand by Brazilian companies for well-qualified professionals in Information Technology (IT), the Brazilian educational system has not been able to meet this demand in a satisfactory way, especially the quality of vocational training question. One way to address this training problem has been the creation of specialized postgraduate courses in IT area focused on students already graduated and working in the IT market. To facilitate access to the course for these working students we opted for offering a Distance Learning model through a Web-based platform. Hence, this paper describes the structure and the experiments conducted over three offers of this course, in 2010, 2012 and 2014, which sought to resolve and measure various problems associated with Distance Learning, such as the sizing and scalability of teachers and tutors in relation to the number of students. Another problem tackled was student isolation, which was dealt with proactive attitudes and motivating actions by the tutors and teachers with tools such as chat, forums, FAQ and e-mails. The problem of "student authentication" was overcome with in person periodical evaluations, plus continuous monitoring of the monograph thesis development by her/his supervising teacher and a final oral defense of the thesis.