The Web and its underlying technologies enable interactions among people that were unimaginable a few years ago. An important type of purposeful interaction is collaboration. Mediated by the Web, people from different social and cultural backgrounds, with different needs, preferences and capabilities can collaborate with each other. Collaboration often takes place in heterogeneous contexts that are not only defined by the actual situations of the collaboration partners, but also by individual and collective past experiences. The Web as a medium has an impact on collaboration and facilitates or enables certain aspects of collaboration while making others more difficult.In this PhD thesis we investigate Interaction Design related questions about webmediated collaboration under a Pragmatic Web perspective. Our prime objective is to understand semiotic barriers to web-mediated collaboration and propose an approach to Interaction Design that reduces these barriers. Semiotic barriers are barriers related to communication, mediation and representation. These barriers emerge during web-based collaboration since many mechanisms of interpersonal face-to-face communication are not available. Depending on the context, semiotic barriers often have a negative impact on collaboration, but in some cases they might also have positive effects.The approach to Interaction Design proposed in this PhD thesis is rooted in the Pragmatic Web and uses Organizational Semiotics and Activity Theory as its theoretical and methodological frames of reference. The theoretic investigations were practically grounded in real world practices by participating in a research project in the domain of inclusive education. We materialized the proposed approach in the design of a prototype and the implementation of the corresponding tool that supports a practice of inclusive education professionals. Furthermore we proposed and applied a pragmatics-driven evaluation method in a longitudinal case study. Prototype design, tool implementation, and the conducted evaluation provided evidence that the proposed approach to pragmaticsdriven Interaction Design can reduce semiotic barriers and thus promote web-mediated collaboration.ix Luckily, writing a PhD thesis is not a solitary enterprise. During the last years, I had the privilege to collaborate or exchange ideas with many people who knowingly or unkowingly left their marks on this work. First and foremost, I would like to thank my orientadora Cecilia Baranauskas who inspired, challenged, and guided me, finding always the right dose and setting an example on a professional and personal level.My thanks go to the dwellers of sala 71 and sala 90, "old" and "new", who shared many a nice conversation and not less lunch, cups of tea or coffee: Alessandro, Elaine, Leonardo, Roberto, and Vanessa. I would like to thank the people who gave me the opportunity to participate as co-author of their work: