Digital products are rapidly shaping our world into a ubiquitous computing world. Because of its unique characteristics, digital artifacts are generative and highly evolving through the recombination of existing elements as well as by the invention of new elements. In this thesis, I first propose an evolutionary view to examine how digital artifacts can evolve over time based on the discussion of limitations of existing approaches. Then, inspired by contemporary evolutionary thinking and phylogenetics in biology, I develop a set of analytic approaches to classify different evolutionary patterns based on the evolutionary rate and evolutionary direction of the digital artifact. In three studies, I investigate digital evolution in specific contexts: web Mashup development, open source software development and digital design practice. I conclude my thesis by highlighting the contributions of my work, and summarizing current limitations and opportunities for future research. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]