This project will develop an information-theoretic analytical framework for the modeling and analysis of limited discretionary regimes (LDRs): situations in which institutional structures restrict, bound, guide, or constrain the discretion exercised by actors within them. Specifically, it will develop the analytical framework and customize it for modeling LDRs, demonstrate, with analytical proofs and simulated evidence, the soundness of the framework for application to LDRs, and apply the framework for modeling the determinants of judicial discretion exercised by Federal judges under the Federal Sentencing Guidelines. In applying the proposed analytical framework to a real-world LDR, the project aims to demonstrate the information-recovery potential of the proposed strategy with regards to an expanded array of research applications. The proposed project will enhance the set of analytical tools at the disposal of researchers, practitioners, policy-makers, and educators.