One of the "paper cuts" developers have been having with developing their MonoTouch 4.0.x (and earlier) applications is that for some networking setups, the IP of the developer's workstation detected by MonoDevelop and given to the iPhone or iPad device for debugging purposes is not correct. This often happens if the WiFi is a different network than the network that the developer's machine is connected to (although there are other scenarios as well).
Since it does not seem to be widely known about, allow me to point out that current versions of MonoTouch allow developers to modify the IP that the runtime should connect to for debugging via the iOS Settings app found on any iPhone or iPad (or Simulator). You can see a screenshot of this per-App Settings page in the screenshot to the left. Each of these fields are editable, allowing you to override the defaults filled-in by MonoDevelop.For our upcoming 4.1 release, Rolf Kvinge and I (but mostly Rolf) have been working on improving this. Rolf has modified the code to check the value of the IP provided in the per-App Settings and if it is set to nil or "automatic", the debugger falls back to checking for a file bundled with the app called MonoTouchDebugConfiguration.txt which can list any number of IP's to try and connect to, each one being on a separate line prefixed with "IP: ". For example:
IP: 10.0.1.31 IP: 192.168.1.31 IP: 22.214.171.124
The runtime will then attempt to connect to each of these IPs asynchronously until it establishes a connection to one of them (at which point it aborts the other waiting connections). This config file solution will hopefully help simplify things for developers a bit by allowing them to pre-configure which IPs to try for their local network configuration w/o having to manually override the iPhone debug settings on the device or simulator.
For Phase 2 of our plan for World Domination, Rolf is hard at work adding support to MonoDevelop and the runtime to allow for USB debugging which will obsolete the above functionality in future versions where the developer has a MonoDevelop which supports USB debugging. For developers stuck on an older MonoDevelop (like 2.4), the solution illustrated above requires no changes to MonoDevelop and so will be available for use.