Dapper 3.27 - Transfer data from iTunes to your digital audio player.

Dapper makes transferring your playlists, music, and album art from iTunes to your digital audio player easy! It supports players with single or dual storage that can be seen by OS X as disk drives (FiiO, iBasso, HiFiMan, etc.).

Use a simple slider to select which artists' music will be copied to which storage device, and see in real-time what amount of storage will be used as a result.

Dapper supports a host of options:

Multithreaded to copy to two drives simultaneously.
Auto sync on DAP connection.
Clean up OS X files on DAP storage.
Reformat capitalization of filenames.
Warn when more than n MB of data will be changed.
Version 3.28 (3.27):

Note: The downloadable demo is version 3.27; the version available for purchase on the Mac App Store is version 3.28.

Fixed a bug where users would be warned erroneously of an unwritable drive in some cases

OS X 10.8 or later
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