In the decentralized Swedish school system, the local education authority (LEA) level has an important position when it comes to school governance. This article takes a micro-level perspective on principals' perceptions of autonomy and control as they navigate local school administration in their front-line work in low - socio-economic status (SES) communities. The point of departure is taken in a multidimensional understanding of principal autonomy and street level bureaucracy. Empirical data consist of group conversations among principals, all of them working in a highly segregated Swedish city. The analysis shows that the principals perceive local school administration to be dominated by uniformity expressed through digitalization and specialization lacking contextual adaption. This orientation gives the principals a sense of local school administration being controlling and non-supportive. In addition, lack of adaption to the specific conditions of the low-SES community context tend to increase the principals' workload and further restrict their autonomy. To cope with the situation and still deliver the education the students are entitled to, the principals act pragmatically in an innovative way. Based on contextual awareness they delay demands, deviate from routines and come up with alternative solutions, hence expanding their autonomy and intensifying their professional judgement.