Systems, methods and computer program products are provided for testing whether Web content has been properly tailored by a transcoding proxy for display within various requesting pervasive computing devices. Simulated HyperText Transfer Protocol (HTTP) requests are built using information from one or more data files. Each simulated request includes a Uniform Resource Locator (URL) that identifies a location of Web content. Each simulated request also includes an HTTP header containing information about a respective pervasive computing device. Simulated HTTP requests are asynchronously issued to respective Web servers identified in the respective HTTP requests. An HTTP response to each respective simulated HTTP request is received and includes Web content tailored for display within a respective pervasive computing device associated with the respective simulated HTTP request. Each HTTP response is then compared with an expected HTTP response. An HTTP response that does not compare favorably with an expected HTTP response can be saved for later analysis.