Schools in the US have often been held up as exemplars of loose coupling between an organization’s environment and it’s technical core; that is, with respect to schools classroom instruction.  Still, the external environment of America’s schools has changed substantially over the past few decades as federal, state and local government regulation focuses increasingly on the technical core.  In this paper we examine the school level or school administrative response to a changing external environment exploring how schools deal with the regulatory pressure for coupling between the external and the technical.  We examine school leaders’ efforts at coupling administrative practice with both the regulative dimension of the external environment and with the technical core by designing and redesigning organizational routines intended to transform school administrative practice.  School leaders’ espoused theories suggested that these organizational routines were intended at coupling the administrative with the external environment and with the technical core.  Further, our account shows that the external environment, especially the regulative dimension, and aspects of the technical core featured prominently, if selectively, in the performance of organizational routines.