The degeneration of source code due to maintenance is a long known but little understood phenomenon. The lack of automated metrics designed to identify degenerate forms contributes significantly to logistical problems faced by current researchers when conducting empirical studies and experiments, studying large-scale projects, and characterizing the development and growth of degenerative forms. Furthermore, such metrics are essential for targeted refactoring and repairing degenerative forms. This dissertation research investigates a set of metrics targeted at specific degenerate forms common in software. The successful implementation and characterization of such metrics will enable further work along these lines.