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kenlotterman

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Sound works from all sources to speakers and headphones except one source does not play on headphones

The computer in question is a Dell OptiPlex 390 with Windows 7 SP1.  The "sound card" is Conexant HD Audio

Suddenly, The transcription software will not play through headphones.  Unplug the headphones and it plays through the system speaker.  Everything else plays through the headphones, just not this one program.  

Again, streaming radio, windows sounds, mp3s play to the speakers AND the headphones, if they are plugged in, but the transcription program ONLY plays through the speakers, not the headphones.  

I've tried it on the front and back jacks.
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John
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Have you tried fully uninstalling the transcription software and reinstalling it?  Restart in between uninstall and reinstall.
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Ramin

Uninstall Sound Card driver, restart, and reinstall it.
Try this,

while playing with  transcription software and headphone is plugged in, click on Speaker Icon on the notification bar, select mixer and check the Volume.
Have you checked to see if the transcription software itself has any sort of preferences to control sound output? I've run into something like this with some computer games I play, where the game has its own custom setting for sound output. It can override whatever the system default is and I've had to set it to my desired output (granted, this was for a setup with USB headphones, so your mileage may vary...)
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I, and the tech support guy (who said VERY boastfully "I'll fix it") did all those things.
If you replaced the software AND the driver AND did all the other, then consider doing a Repair Install of the operating system.

Failing that, it would then be a hardware problem.
Have you tried turning up the volume on the transcript program
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kenlotterman

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I had not accepted any of the answers because the issue went away and I forgot to accept.