I was playing around debugging a custom app in one of my Windows 7 & Visual Studio 2010. When I tried running msvsmon.exe (Remote Debugging Monitor) and got the following error message when attempting to remote debug:

Error while trying to run project: Unable to start debugging.

This operation returned because the timeout period expired.

During further investigation, I found that the issue is that the firewall is not setup properly on the Win7 machine for remote debugging. I noticed that when msvsmon first launches, it will prompt the user to configure the firewall.

Per the debugger blogpost, this happens due to the firewall security API changes since Vista, the prompt may not come up. I tried the following workaround to move ahead:

Control Panel->System and Security->Windows Firewall: Change notification settings -> enable Notify me when Windows Firewall blocks a new program ->Ok

After implementing the above, I started remote debugging again and this time I can notice that msvsmon shows popup a windows security alert dialog box that prompt to grant access permission to msvsmon.

Happy debugging!!