I haven't been able to get this to work.

As far as I know you can only select one output at a time - either through the dock or through the Mac's speakers.

Then consider upgrading:

Upgrading to Mountain Lion

To upgrade to Mountain Lion you must have Snow Leopard 10.6.8 or Lion installed. Purchase and download Mountain Lion from the App Store. Sign in using your Apple ID. Mountain Lion is $19.99 plus tax. The file is quite large, over 4 GBs, so allow some time to download. It would be preferable to use Ethernet because it is nearly four times faster than wireless.

OS X Mountain Lion - System Requirements

Macs that can be upgraded to OS X Mountain Lion

1. iMac (Mid 2007 or newer) - Model Identifier 7,1 or later

2. MacBook (Late 2008 Aluminum, or Early 2009 or newer) - Model Identifier 5,1 or later

3. MacBook Pro (Mid/Late 2007 or newer) - Model Identifier 3,1 or later

4. MacBook Air (Late 2008 or newer) - Model Identifier 2,1 or later

5. Mac mini (Early 2009 or newer) - Model Identifier 3,1 or later

6. Mac Pro (Early 2008 or newer) - Model Identifier 3,1 or later

7. Xserve (Early 2009) - Model Identifier 3,1 or later

To find the model identifier open System Profiler in the Utilities folder. It's displayed in the panel on the right.

Are my applications compatible?

See App Compatibility Table - RoaringApps.

For a complete How-To introduction from Apple see Upgrade to OS X Mountain Lion.