The purpose of this study was to explore patterns of learning among adult learners in a Web-based learning environment over the study period of one year in the Open University in Tampere and Lohja in Finland. The learning environment varied from face-to-face small group sessions to Web-based online discussion sessions. During this study contextual orientation formed the main concept describing orientation differences in learning, in the metacognitive management of learning, and in the construction of own expertise. The adapted grounded theory analysis demonstrated two main contextual orientations in the Web-based learning environment. These are described and discussed. If learning goals and general approach to learning serve learners' interests in developing their own know-how and expertise, goals and targets of learning are wider than those offered by the learning environment. However, most adult learners did not apply this approach during their studies.