Recent CALL technology reviews cover a plethora of technologies available to language learners to improve a variety of skills, including speaking. However, few technology-enhanced self-access tools are available for pragmatic development, especially in oral modality. Recognizing the benefits of structured practice for second language development, we demonstrate how such practice can be incorporated into three recently developed simulated speaking environments that vary on the targeted L2 (French, English), domain of use (academic or everyday interaction), emphasis on higher-order and/or lower-order skills, and accommodation of multiple L2 varieties. In the spirit of finding synergies and learning from each other's experiences in specific local contexts, we address the following research questions: (1) How does the local context, researcher and learner goals, and technological possibilities influence the design of each computer application? (2) Based on the examination of the three programs, what can we learn in view of redesign options and suggest to future developers of such programs?