This looks promising: http://developer.valvesoftware.com/wiki/Command_Line_Options It appears (from a quick glance, seeing "allowdebug" and "-dev") that you can debug by simply passing the right arguments to hl2.exe. No external debugger. Maybe you can use hl2.exe as it's own debugger. Right now I'm pretty dubious that hl2.exe can work in gdb. For three reasons: 1) I tried and it didn't work. 2) I'm pretty sure hl2.exe wasn't compiled in gcc or even compiled to be compatible with gdb. 3) You don't have the hl2.exe source code (or do you?). I think you'll have to change tactic and use hl2.exe "debugging?" parameters (I hope they are) or use Wine's debugger. Anytime I Google "debug hl2.exe" Visual Studio usually comes up. I don't think that's for debugging hl2.exe itself, though: > A message will appear indicating that symbols cannot be found for hl2.exe. This simply means that there is no debug information for hl2.exe, but we aren't particularly interested in hl2.exe itself. It is our Client.dll and Server.dll made by our project that we will be debugging. Check Don't show this dialog again and click Yes. Your mod will now load several modules, and several seconds later your mod will appear. It is recommended to edit the video options, and select windowed mode. This will make it easier to switch back and forth between your mod and VS. -from http://developer.valvesoftware.com/wiki/Launching_from_Visual_Studio Cheers, Jake Cheers, Jake