I'm having problems getting the sound "Portal.room1_Radio," the song the tiny portable radio prop plays, to play the way I want it to in a map. I'm trying to make it audible from everywhere inside a room that is about 1500x1500x500 and also directional so that the player will be drawn to look at the source of the music (a window where something is happening).

The problem is that no matter what way I set it to play it is only audible for a range of about 256 units. I've tried using an ambient_generic with the max audible distance set to 3000 and both with and without the "play everywhere" tab checked, but it always has the same range limit. I've also tried spreading ambient_generic entities playing the same sound throughout the room, which causes the individual sounds to slowly drift out of sync (this appears to depend on player proximity).

Does anyone have any ideas?

Portal.room1_Radio is a game sound, it has already been set ranges, dsp effects, volume and many other things on a soundscript file.
You have two solutions:
-Use the Raw file, using its directory (filename ending with .wav or .mp3).
-Create your own custom soundscript file.

http://developer.valvesoftware.com/wiki/Soundscripts

Thanks for the info. I've got it sounding okay now.