Here's what I recommend you do.
1. Do you have your transcoders setup in /var/subsonic/transcode (you may need to make the directory first)?
You need Lame (available in Debian repositories) and ffmpeg (available in Debian repositories). You should make symbolic links to where the transcoders are located.
Run
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which lame
to find out where lame is installed then run the following.
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ln -s /var/subsonic/transcode/lame /usr/bin/lame
Where /usr/bin/lame is the result of running the previous which command.
You should do the same process for ffmpeg.
2. Check the subsonic log. Should be located at /var/subsonic/subsonic.log
On the debian server you can run
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tail -f /var/subsonic/subsonic.log
and watch the log as it grows. You can post the output of you attempting to play a file here (please use the [ code ] bb code)
3. Check the format of the media you're trying to stream is set up in transcoding in Settings > Transcoding.
Also check that your player has that transcoding enabled (Settings > Players)
4. In the web browser check you have the right player selected from the drop down menu near the bottom.
5. Check the web browser you're trying to use has the latest version of adobe flash installed and enabled.