There could be a couple of things causing this.  Do you have ALSA's OSS Emulation properly configured.  If you do, you should be able to hear sound when you #echo /dev/rand > /dev/dsp .  If /dev/dsp isn't working, please refer to the Gentoo Wiki article on setting up ALSA properly for OSS Emulation.  http://gentoo-wiki.com/HOWTO_ALSA_Complete_%28includes_dmix%29

You may also want to check on which version of ALSA you're using, because prior to ~0.9, dmix wasn't automatically enabled (software mixing) and if your sound card doesn't support hardware mixing, other devices will tie up /dev/dsp and not allow Skype access.  Skype is very stingy when it comes to sharing /dev/dsp.

Let me know what you come up with.

Jason Weisberger

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