This book describes how traditional chalk and talk lectures can be transmitted over the web while improving the classroom experience at the same time. Describing a compelling alternative to slide-based lecturing the book presents a comprehensive discussion of many technological and human-centered challenges and solutions using the example of the software system E-Chalk that was co-developed by the author. As a by-product the work includes the Simple Interactive Object Extraction (SIOX) algorithm that has been the open-source standard for interactive image segmentation for the past decade implemented in image manipulation programs such as GIMP Inkscape and Blender or the US National Institute of Health''s ImageJ library.