The iTunes application doesn't support FLAC file format. Currently, iTunes can read, write, and convert the following audio formats: MP3, AIFF, WAV, MPEG-4, AAC and Apple Lossless (.m4a). To play the FLAC file in iTunes, you need to convert your files to a format supported by iTunes. You can either use an application like dbPowerAmp or browse the database of Software Informer to look for additional audio converters. You can use dbPowerAmp for 21 days without restriction.