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At least D[n]A gave us a quite complete description of of what he have done... wrong. As said bluecrab there is an error with the connections : To be connected with a PC witch has an internal or an external soundcard with an OPTICAL OUT (S/PDIF toslink) you need to connect it with the OPTICAL IN (S/PDIF toslink) of your deck. This is for a ditigal real time recording (also to make work your deck as a DAC). What you absolutely need to be sure, is that the signal use at the maximum the 48kHz frequency. That is the case for all the music if not a "Hi-Res" quality (Hi-Res mean Hi-Resolution a.k.a. 24bits-48kHz and superior like 24/32bits - 96-88,4kHz-192kHz and much more (DSD quality). A CD is 16bit-44,1kHz quality so if you create Flac (lossless) files with it on your PC, you will get 16bit-44,1kHz tracks files that Winamp can read. Till you don't want to record Hi-Res music who can keep Winamp and the WinCue plugin to be sure to get finally separate tracks (all silence tracks can be easily deleted by hand or better with Sonic Stage when you also get the time to edit and to title all the tracks). Note that foobar2000 is another good alternative, as foobar2000 can read Hi-Res (SACD plugin), WinCue is replaced by the Post-track silence plugin. Personnaly I use the jRiver Media Center audio player but it is a factory gas station for a beginner. Hi-Res music can be record in real time to your MD deck if you use the Digital Signal Processing (DSP) Sox (resampling high frequencies to 48kHz). You can use the OPTICAL OUT of the deck to connect it to the OPTICAL IN of a Digital Receiver (then listening your music in stereo or 5.1) or of a modern DAC wich could enhance a lot your music. About the recording level, you can choose (or not) to apply ReplayGain* to all your tracks. Wikipedia : ReplayGain normalize loudness for individual tracks or albums. This avoids the common problem of having to manually adjust volume levels between tracks when playing audio files from albums that have been mastered at different loudness levels. Then you adjust the deck recording level for the first tracks and that is done for all the other tracks. (*) not sure this is possible using Winamp... that why foobar2000 will be your next best friend !

You're trying to record an MD? Then the cable needs to go into Opt. In. of the deck.