A method, apparatus and computer program product are provided to model and manage context-based entitlements that govern a user's access to information, applications and systems across a loosely-coupled distributed environment. One such distributed environment is a federated environment, which may span across companies, organizations, and geographical locations and regions. According to one embodiment, an entitlement modeling framework comprises a discovery module and an entitlement generator module. The discovery framework generates a data model for storing information concerning user identity, context, relationships between users, relationships between users and contexts and relationships between contexts. Preferably, the user identity, context, relationships between users, relationships between users and contexts, and relationships between contexts, are stored as attributes in the data model. An entitlement generator generates an entitlement according to the data model, wherein the entitlement (e.g., a user entitlement) is generated according to one or more contexts.