The researcher combined qualitative media analysis with tools for discourse analysis to review Blackboard Collaborate™, a tool often used in online education. Technology design references Discourses which dictate how and why these tools should be used. The analysis showed Collaborate™ uses sign systems and knowledge, along with politics, to reinforce a traditional educational Discourse. Educators should be aware of embedded Discourses to effectively incorporate technology into their practice, and designers should consider such Discourses during development. This paper describes discourse analysis as one approach to evaluating technology with regards to affordances for, and constraints to, teaching and learning.