Workplace learning (WPL) of students constitutes an integral part of the engineering curriculum at the Department of Electronic Engineering – Technological Educational Institute of Crete (DoEE/TEIoC). More specifically, the six months’ workplace learning duration of our students is carried out through internships between the DoEE/TEIoC and enterprises/organizations. In our economic recession times, such collaborative internships are confronted with various challenges related to pedagogical, labour market, organizational, etc. issues. The aim of the paper is to provide insights to our experience as it concerns the exploitation of practices we adopted in a social web context towards the achievement of an effective workplace learning for all parties (students, enterprises/organizations, DoE/TEIoC) involved. Emphasis will be given to students’ weblogs and podcasts in order to guarantee quality outcomes for the overall workplace learning process. Furthermore, based on data available from questionnaires filled by our students as well as by the corresponding enterprise/organization and academic supervisors, a series of internship related implications and prospects are identified and discussed.