As part of redesigning our introductory programming sequence, Anonymous University removed formal prerequisites from each course, allowing students to self-select into whichever course they believe best fits their experience level. To help facilitate these choices, we developed a guided self-placement tool that offers course recommendations based on students’ previous experience and confidence with course topics. In this report, we describe the design and implementation of the self-placement tool and reflect on its first years of use. The tool has been effective, with most students reporting that they used the tool, followed its recommendation, and are confident in their enrollment decision. The rates of students switching or dropping courses within the introductory sequence have been low. In addition, results from a preliminary interview study show that all students who followed the tool’s recommen- dation believed the suggested course was the right choice. Most students who opted for a different course were influenced by exter- nal factors, largely related to their confidence in the course content and perception of course difficulty levels. We conclude by reflecting on what we have learned so far and laying out next steps.