In this work we deal with a multi-layer caching architecture capable to optimize delivery of dynamically produced web content. With reference to such architecture, we propose a technique named Pinball Caching, representing a useful means to estimate attainable performance improvement with respect to the trend of the main parameters characterizing the system. The application of such instrument allows clearly identifying where to concentrate efforts in order to optimize the joint utilization of the content adaptation architecture on one side and the hierarchical caching pool on the other.