This article proposes an approach to teaching street crossing to students who are visually impaired that considers the risks, ambiguity, and complexity of today's intersections. Thirty or 40 years ago, street crossing was a straightforward task for travelers with visual impairments (that is, those who are blind or have low vision). The intersections were predictable, and there were standard, highly successful procedures using reliable vehicular sounds for crossing them safely (Jacobson, 1993; LaGrow & Weessies, 1994). Of course, there was risk in crossing, as there is risk in everything we do, but the risk was manageable and was considered acceptable if the proper procedures were followed. Today, the task of crossing streets is complex. Intersections and traffic signals are unpredictable (Barlow, Franck, Bentzen, & Sauerburger, 2001), right-turn-on-red and other features require adaptations to the standard street-crossing procedure (Sauerburger, 1998), cars are quieter, and vehicular sounds are no longer reliably present (Barlow, Bentzen, & Tabor, 2003; Bentzen, Barlow, & Franck, 2000; Carroll & Bentzen, 1999; Sauerburger, 1989, 1995, 1999). The population of independent travelers with visual impairments who cross streets now includes people with additional considerations (such as elderly people; children; and people with cognitive, mobility, and/or hearing disabilities in addition to visual impairment) that require adaptations to the standard street-crossing techniques. As a result, the questions of how and where to cross and even whether it is possible to cross a given street safely come up more and more frequently. The ambiguity and complexity in street crossing today requires an approach to teaching street crossing that addresses such questions. This article presents an approach that seems to address these issues satisfactorily.