Virginia Commonwealth University (VCU) is implementing a large scale exploration of digital pedagogies, including connected learning and open education, in an effort to promote digital fluency and integrative thinking among students. The purpose of this study was to develop a classroom assessment toolkit for faculty who wish to document student connectivity in course-related blogging and microblogging ("tweeting") activities. Student use of digital annotation devices, including hyperlinks, embedded images, mentions, and hashtags, were studied in four university courses as potential indicators of student connectivity, defined as the ability to connect current thoughts and experience with other concepts and people across space and time. One thousand one hundred and eighty six (1186) hyperlinks and embedded images, 2708 mentions, and 135 hashtags were collected from 498 learner blog posts and 5343 tweets through mostly automated, digital workflows and analyzed through a combination of statistical, content, and network analysis. General criteria for "connected course" design, a model for connectivity as a form of learning, connectivity-based learning goals, and integrated, potentially scalable assessment practices are discussed. Content analysis led to the development of classification systems for the types, sources, and communicative impact of hyperlinked and embedded materials in blogging and tweeting contexts. Network analysis was adapted to visualize, document, and describe course-related social interactions and student use of web-based information sources. Real student data are used to describe annotation-focused assessment criteria, analytic assessment dashboards, rubrics, and approaches to real-time graphic visualization of student performance. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]