Deleting files on startup

[Fitzhugh ONeill]

I am having difficulty syncing audio files to my cell.
I downloaded 300 files and when I turned off the phone;
and turned it back on, then launched winamp, it deleted all but 40 files.
Those files did not play but skipped and then stopped.
The info on my setup is below:
Cell LG-P505
Android version 2.2.2 Sftw V1Di
Winamp 1.1.1
Winamp 5.621
32GB simm Card