Purpose: This study builds on research scrutinizing school autonomy in policy and school governance by shifting the focus from a formal structural view of autonomy to examining how principals negotiate autonomy in their daily work. Drawing on multiple dimensions of autonomy and street-level bureaucracy, this study examined how principals, as both professionals and bureaucrats, work to expand and strategize their autonomy in practice. Research Methods/Approach: We used portraiture to document and interpret the experience and perspectives of three principals at urban, suburban, and rural PK-12 traditional public schools in the Midwest of US during the 2018-2019 school year. Findings: Principals faced a "bounded" or "partial" autonomy in which they had to constantly negotiate their individual autonomy (e.g., how they spent their time on any given day) with institutional autonomy (e.g., the demands of the role via external expectations). The findings show the ways participants utilized institutional autonomy to support individual autonomy and dealt with the boundaries of their autonomy. While these strategies gave them a bit more "control" over decision-making, they also often resulted in overwork and/or conflict with district priorities. Implications for Research and Practice: Detailed portraits offer key insights for rethinking school autonomy with multiple dimensions intersected in leadership practice. Findings yield knowledge regarding how to best support districts and school leaders in creating greater alignment between institutional and individual demands, thus increasing the likelihood that autonomy, as an improvement strategy, can be effective.