My district recently purchased licenses for Illuminate Education, which is an assessment application. District leadership hopes that Illuminate will become a district-wide gradebook as we transition to standards-based grading. This will eventually replace the use of our SIS, PROMIS, as our report card tool. However, teachers currently use Google Apps for Education (GAFE) and Haiku Learning as our learning management system. With these two tools, teachers are able to create assignments in Haiku that are directly tied to a standards-based gradebook and students are able to assignments work by attaching documents from Google Drive. If the district adopts Illuminate as a district-wide gradebook, this feature will be lost because Illuminate is not GAFE compatible. As a result, students will need to download and upload documents to submit assessments and/or learning will become less transparent to guardians/partner agencies. In order to see challenges such as this district leaders need to step back and examine all major applications in order to better understand how they work--or do not--work together. This approach allows leaders to take a preventative and proactive approach before the licenses are purchased and time has to be spent reacting to unforeseen challenges.