Teacher quality is the most important school-based factor affecting student learning and achievement. In 2009, the Race to the Top (RttT) federal education initiative provided an opportunity for states to compete for federal grant resources to reform their public education systems, which included revamping teacher evaluation systems to improve teacher (and principal) effectiveness. Consequently, New York State was awarded almost $700 million in 2010 during the second phase of RttT for its Regents Education Reform Plan, which established a new teacher and principal evaluation plan known as the Annual Professional Performance Review (APPR). Under its first version (§3012-c), APPR used multiple measures, which included student achievement measures, and was intended to inform retention, termination, and tenure determination along with high quality professional development. However, APPR has been criticized for its hasty implementation and controversial use of student outcomes measures to evaluate teachers. Although APPR went into statewide effect for all public school districts during the 2012-13 school year, this study seeks to examine how teachers perceive teacher evaluation and building principal leadership after five years of engaging with APPR. In particular, this study also seeks to examine the relationship of building principal leadership on teacher perception of APPR through the sense-making process (Spillane, Reiser, & Reimer, 2002).An online constructed response survey instrument was distributed to a census of Core Content Area (CCA) secondary teachers working within 27 public high schools configured as a separate 9-12 building within New York's Capital Region. In addition, school, district, and teacher evaluation-level data were also collected from submitted district APPR plans (§3012-d) and online resources such as the NYSED Data Site and NCES School & District Navigator. This information was integrated with collected survey instrument data completed by 414 CCA secondary teachers. Data analysis demonstrated that after five years of engaging with APPR, including its revision to §3012-d, (a) teacher perception was generally positive towards teacher evaluation in the areas of practicality and clarity, but not as it related to need and utility; (b) teacher perception was fairly positive towards building principal leadership in the dimensions of support of teaching, initiating structure, vision, and trust and confidence; (c) tenure status and teaching experience was related with how teachers perceived both teacher evaluation and building principal leadership; (d) NYSED accountability status in combination with district N/RC classification were related with how teachers perceived teacher evaluation; and (e) building principal leadership in the area of initiating structure positively impacted how teachers perceived teacher evaluation regarding practicality, clarity, and most importantly, need. These results indicate that APPR is largely in a state of compliance. However, findings from this study also suggest that APPR is positively affecting probationary teachers in the early stage of their professional careers. Moreover, additional results also demonstrate the potential of building principal leadership to positively support probationary teachers and veteran, tenured teachers and more effectively engage them with APPR in support of further developing teacher growth and informing school improvement efforts. Conversely, findings from this study also indicate that APPR may be ill-suited to effectively support teachers working in urban priority or focus high schools within high N/RC districts. Consequently, this study recommends that building principals remain connected to the instructional core and make a concerted effort to structure time to deliberately engage teachers in frequent, sustained, differentiated, and collaborative professional development informed by APPR's teacher practice rubric, teacher evaluation data, and school-level goals. Moreover, building principals must remain conscientious to skillfully allocate time to support transformative change by leveraging APPR to facilitate professional teacher growth versus engaging in transactional change by only completing APPR's required tasks. On the one hand, APPR has succeeded in largely having an effective teacher in every classroom since almost 95% of all New York State teachers have been rated as effective or highly effective over the first five years of APPR under §3012-c and §3012-d (New York State Education Department [NYSED], 2018-b). However, it is equally important to evaluate APPR's ability to effectively "foster a culture of continuous professional growth" for teachers to "consistently improve their instructional and management practices" (NYSED, 2018-a). Accordingly, further research is needed to explore the extent to which public schools have fully integrated APPR into professional development practices in a meaningful and sustained manner. 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