The rapid growth of online and blended learning environments in both higher education and K-12, along with the development of innovative game based, narrative driven, problem-based learning (PBL) systems known as Alternate Reality Games (AltRG), has led to the need to understand student’s abilities to self-regulate their learning behaviors and practices in these novel environments. This study examines student reflections and e-mails related to self-regulatory practices for learning across two different course designs for an Internet-based course in computer applications. Both designs leverage PBL but apply different levels of abstraction related to content and the need to self-regulate. The study looked specifically at how students communicated about learning across these environments, what student communications indicated about student readiness for university online learning and how instructional design and methods of instruction shaped student expressions of learning and self-regulation. The research design follows an ethnographic and case study approach as two designs and four sections are examined. Data was collected from student blog posts, email messages and semi-structured interviews. Atlas.TI was used to code the data using constant comparative analysis. A sequential analysis was applied using an a priori structure for self-regulation and post hoc analysis for emergent codes that resulted in the following categories: distraction, group experience, motivation, emotion, prior experiences, and time. Results indicated qualitative differences between the two designs related to student communications for learning and self-regulation. Findings were reported for both the a priori and post hoc analysis. Additionally, two major findings are reported as emerging themes. These are presented and discussed as The Expectation Gap and Different Designs, Different Outcomes.