This report will focus on challenges we faced maintaining hundreds of builds that encompass tens of thousands of assertions. Over the past five years our development team, at Iowa Student Loan (ISL), leveraged TDD and Continuous Integration to develop software. Tests and builds quickly accumulate and maintaining them can be like herding cats. We were often tempted to neglect these tests in the pursuit of developing new functionality. We would like to share strategies that helped us maintain our automated test investments.