I'm writing this post because this was asked so many times over, but nobody seems to have come up with a good answer. People suggested some trials of paid programs, but that's not really an everyman solution. I don't know on how many machines my workaround will work, depends on the audio chip. I'm going to tell you how to do this in foobar2000. My system is Win7. 0) I think that this will work only if you see something like this in your Playback devices (right-click windows audio icon & select from menu to launch it): So if the headphone output is not "Ready" when nothing is plugged into it, you will maybe be able to use the HDMI output if you feel adventurous, or for that matter any output that you have. You possibly have no idea why I'm talking about that, but this will be clear after reading through the rest of my little manual. ------------------- 1) download & install foobar2000 here: http://www.foobar2000.org/download play around with it of you don't know the player. 2) download & install the latest ASIO4ALL here: http://www.asio4all.com/ leave all install options default. 3) download ASIO support for foobar2000: http://www.foobar2000.org/components/view/foo_out_asio double-click it, fb2k will install it automatically. 4) go to foobar2000 file->preferences->output->asio. Check if asio4all is visible at the top list. You can use the x64 driver (requires foobar2000 restart) 5) Add a new channel mapping. Don't change the name, you won't need it anyway. click "configure" 6) ASIO4ALL window will pop up. Enable advanced settings (bottom right). 7) now there's the icky tricky part. Click the [+] next to all and enable all the outputs that you like (sometimes the HDMI output is also there). What you really need is sth like "internal speakers out" and "HpOut". On my computer (Dell Inspiron 15R) it looks like this: 8) IF YOU CAN'T SEE TWO OUTPUT DEVICES HERE YOU WILL PROBABLY NOT BE ABLE TO DO THIS. Sorry (everything depends on how your soundcard handles it, maybe connecting the headphones will make it appear? Try around). 9) Click "cancel" (this was for other outputs to appear) 10) Click "Add new". Rename it to "int+ext" or whatever. 11) Map <channel_name> 1 to the Left channel and <channel_name> 2 to Right (you can play with that, even build a faux surround with a bit of luck). Play test signals if you're not sure where each channel should be. On my machine it's like that: 12) Click OK, Apply, then restart fb2k and go to file->preferences->output 13) Select the output: ASIO : int+ext. Click OK. Play your favorite piece of audio If you did everything correctly, you should hear all the outputs together. Meaning your internal speakers and the jack-connected headphones or speakers. The sound will work ONLY fb2k, you will have to stop [ ] the music to use any other program that outputs sound. ASIO overrides Windows output. Most music files will work. The method is transferable to any program that can support ASIO. Leave some feedback if it worked for you. Or if it didn't, anything's good.