You need to set the "SteamAppId" environment variable to your hl2.exe's AppId.
For example SteamAppId=218 for SDK Base 2007.

There used to be two other env vars you would need to set but apparently it now works without them (for me with 2007 anyway).

You can do this from within Visual Studio (debug settings for the project).

Am 29.05.2014 08:47, schrieb Nick:
Is this problem still broken? I also cannot debug on vs2005 by directly starting hl2.exe with the -novid -allowdebug -steam -game "moddirectory" parameters.

The only way I can debug w/ vs2005 is to manually attach. I really hope this problem is fixed by now.

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