Technical assistance

Perhaps you should try reformatting or update your firmware.
http://www.insignia-products.com/pc-228-41-insignia-sport-2gb-mp3-player-black.aspx

And for formatting your insignia player go to my computer, insignia media player, right click it and click format, select fat32 and click format. That's all I know that you might be able to try. Otherwise try calling or emailing the company.
http://www.insignia-products.com/t-contact.aspx

Well the songs you are trying to put on your mp3 player are probably too big. You can change your settings in Windows Media Player or (whatever program you use to sync the songs) to convert the songs to mp3 format and change the quality. I suggest changing it to 128 or lower quality. Hopes this helps you out.