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Playback will be gapless if gapless playback is possible. Generally lossless files, ogg, mpc and wma are always gapless. AAC/MP4/M4A and MP3 are special cases. These rely on the encoder and decoder working properly to produce gaplessness. LAME MP3s are always gapless as of 3.90, as are Nero and FAAC AAC files. iTunes files are not gapless.
