A major strand of science and technology studies in recent decades has related to the social construction of technology (SCOT) movement, whose adherents maintain that technological systems are determined just as much by social forces as by technological ones. Taking this SCOT notion as a starting point, and putting a focus on the user, this paper looks at some examples of the educational use of software tools that exploit the functionality of the software in ways far removed from the original design. Examples include the use of spreadsheets, graphics editors and audio editors, and online translation software. Connections are made between the social construction of technology and constructivist pedagogy, particularly in relation to authentic learning. (Contains 5 figures, 1 table, and 3 notes.)