The determination and evaluation of chirogenic properties of molecules are key issues in modern chemistry, pharmacology, and biology. Understanding chirogenic mechanisms and origins is difficult and poses complicated problems as all existing theoretical methods have their advantages and limitations. Hence, appropriate test cases and a proper combination of experimental and theoretical methods are required. Here, we present a model study using a porphyrin receptor and camphersulfonic acid as a chiral analyte to evaluate the state-of-the-art in rationalizing the corresponding chirogenesis.