Some useful tools & tips for debugging iOS apps which connect to web services:
Debugging in the iPhone Simulator
Debugging On-Device
Paros Proxy - free, open source app. In Paros, go to Tools -> Options… select the Local Proxy option. Enter your Mac's IP address and leave the port at 8080. On your iOS device, go to Settings -> Wi-Fi, select the same network as your Mac and tap the blue button. Set HTTP Proxy to Manual and enter your Mac's IP address under Server and 8080 for the Port.
Charles Web Debugging Proxy - On your iOS device, go to Settings -> Wi-Fi, select the same network as your Mac and tap the blue button. Set HTTP Proxy to Manual and enter your Mac's IP address under Server and 8888 for the Port.