The recent design for the reconstruction of Lake Street in Minneapolis, Minnesota, provides the canvas for an illustration of the challenges in delivering a context-sensitive project within the center of a city where a dense built environment already exists. Lake Street's reconstruction involves a county-initiated design, the city's and the community's response, and the participation of a foundation in achieving a design linked to how the community can grow and prosper and how people interact with one another. A street is an integral part of community life. Its design can hinder or support a community. The Lake Street design process shows that this understanding, along with best intentions, is not always enough. Strong institutional biases and conventions drive street design processes toward traffic-moving outcomes and away from community-building outcomes. These biases can be countered only with deliberate forethought and persistent attention and action. This paper attempts to provide insights into how community goals and street design processes become misaligned. Through a case study approach reviewing a current design, it also offers strategies showing how future street design processes must be more than an act of engineering. Good street design is an act of community planning, with engineering expertise helping to execute those plans. Once those involved in street design processes begin to recognize this, the approach will be different, the discussions will be different, and above all, the outcomes will be different.