I have, in EF5, two entities: User and Role. Between User and Role there is a many to many relation. I don't have an entity for the UserRoles database which sets the relation. I have a User and I want to delete a role without loading it from the database. Context context = new Context(); User user = context.Users.First(x => x.Id == 4); user.Roles = new List<Role>(); Role role = new Role { Id = 20 }; context.Roles.Attach(role); user.Roles.Remove(role); context.SaveChanges(); I don't get any error but the role is not removed. Any idea why? Thank you, Miguel