Connotational subtyping is an approach to typing that allows an object's type to change dynamically, following changes to the object's internal state. This allows for a more precise representation of a problem domain with logical objects that have variable behavior. Two approaches to supporting connotational subtyping in the Ruby programming language were implemented: a language-level implementation using pure Ruby and a modification to the Ruby 1.8.7 interpreter. While neither implementation was wholly successful the language level implementation created complications with reflective language features like self and super and, while Ruby 1.8.7 has been obsoleted by Ruby 1.9 (YARV), the results suggest that Chambers-style, predicate-based runtime type inference could be incorporated into Ruby with only some reduced interpreter performance.