In theer study of equity issues in information technology (IT), researchers concerned with workforce diversity often utilize the metaphor of a “career pipeline.” In this metaphor a population full of gender and race diversity enters the pipeline in kindergarten, but its delivery at the pipeline outflow in the form of software engineers and other IT workers is disproportionately white and male. While we might question the metaphor—its lack of attention to economic class or social construction, its illusion of rigid boundaries, etc.—the phenomenon it describes is well established by a broad number of statistical measures. For example, the U.S. Bureau of Labor Statistics’ Current Population Surveys shows that between 1996 and 2002 the percentage of women in the overall IT workforce fell from 41% to 34.9%; during the same period the percentage of African Americans fell from 9.1% to 8.2%. Not only are women and certain minority groups under-represented, but the gap is in some cases getting worse. Returning to the pipeline, we might ask what barriers are encountered by women and minorities that act as impediments to this flow. Some of these barriers can be attributed to economic status; in particular the impact that poor educational resources have on low-income minority student academic success (Payne & Biddle, 1999). But other barriers appear to be more about cultural identity, including both race and gender identity. This essay describes Culturally Situated Design Tools (CSDTs), a suite of Web-based interactive applets that allow students and teachers to explore mathematics through the simulation of cultural artifacts, including Native American beadwork, African American cornrows, ancient Mayan temples, urban Graffiti, and Latin percussion rhythms (see http://www.rpi.edu/~eglash/csdt.html). Our preliminary evaluation indicates that some of the identity barriers preventing women and minorities from participating in IT careers can be mitigated by the use CSDTs in classroom and out of class learning environments.