The main concern of this paper is the exploration of current challenges, teaching techniques, course design methods and topics covered when attempting to teach a web programming course in technology-oriented higher education departments. The authors attempted a literature review of the subject in order to identify, compare and analyse the existing experience upon which one can establish solid guidelines towards a manageable, efficient and comprehensible course model. In the paper, the presentation of the value of teaching web programming is followed by an extensive listing of the underlying challenges. Consequently, the various teaching approaches are presented comparatively and comments are made as regards the topics covered and the tools used. The study and analysis of this gathered experience naturally leads to certain outcomes. An extensive list of questions is summed in a list view and this list aims to help educators of the field to prepare the respective structure, content, methodology and tools of a web programming course that will serve their needs in a productive way. The authors' intention is to build upon this knowledge towards a web-based comprehensible web programming environment that will aid the process of teaching this challenging subject.