This document discusses evaluating software degradation through six versions of the open-source software JHotDraw. Data was collected dynamically from each version using AspectJ to derive two metrics: entropy and software maturity index. Entropy measures complexity and was expected to decrease as the software evolved from adding new features. The software maturity index was derived from documentation and aimed to find if entropy decreases most when maturity is highest, implying a relationship between the two. Six versions of JHotDraw released over five years were tested to investigate changes in these metrics and degradation as the software evolved through new versions.