Since humans first put pen to paper, people have critically assessed written work; thus, the assessment of documents per se is not new. Only recently, however, has the issue of formalized document quality assessment become feasible. Enabled by the rapid progress in computing technology, the prospect of an automated, formalized system of quality assessment, based on the presence of certain attributes deemed essential to the quality of a document, is feasible. The existing Objectives/Principles/Attributes Framework, previously applied to code assessment, is modified to allow application to documentation quality assessment. An automated procedure for the assessment of software documentation quality assessment and the development of a prototype documentation analyzer are described. A major shortcoming of the many quality metrics that are proposed in computer science is their lack of empirical validation. In pursuit of such necessary validation for the measures proposed within this thesis, a study is performed to determine the agreement of the measures rendered by Docalyze with those of human evaluators. This thesis demonstrates the applicability of a quality assessment framework to the documentation component of a software product. Further, the validity of a subset of the proposed metrics is demonstrated. / Master of Science