I recently went back to the Pocket PC camp after using a Smartphone for the last year and I am glad to be back. In the past playing lossless files on your mobile device was a difficult procedure and consisted of hunting for some random plugin that may or may not work. While this can still be true for some formats on a few devices support has gotten much better.
There are currently four main applications available that can play your FLAC, WavPack, APE, etc. files on your Windows Mobile, Pocket PC, Smartphone, Symbian OS and PALM devices. It’s also worth mentioning that all of these applications cost except BetaPlayer.

The Core Pocket Media Player (TCPMP) - The Core Pocket Media Player formally known as BetaPlayer is going back to the BetaPlayer naming convention. Sometime in December a new site we will be available at www.betaplayer.com. Until then it can be found at www.tcpmp.corecodec.org/about. TCPMP supports both audio and video but we will focus on the audio portion.

Current supported formats include: MP3,MP4,M4A,AAC,OGG,WMA,FLAC and WAV.
Devices Supported: Pocket PC, HPC, Smartphone, Palm as well as older SH3 and MIPS based devices.

The CorePlayer Mobile - The CorePlayer is the closed source version of TCPMP and does cost. But it also includes a variety of features that TCPMP does not such as Skinning, Visualizations and Advanced Streaming (RTP/RTSP/HTTP/MMS/UDP) and UPnP support.

Current supported formats include: MP3, AAC, MKA, WMA, WAV, OGG, Speex, WAVPACK, FLAC, MPC, AMR, ADPCM, ALaw, MuLaw and Midi.
Devices Supported: Pocket PC, HPC, Smartphone, Palm, and Symbian

iPlay - Is a server\client setup with a wide variety of features including support for gapless playback. Gapless playback is supported with iTunes 7.0 encoded mp3 and m4a files, LAME v3.90+ mp3 files as well as OGG, WAV and FLAC.

Current supported formats include: MP3,MP4,M4A,AAC,OGG,WMA,FLAC and WAV.
Devices Supported: Windows Mobile 5, Pocket PC 2002\2003 and Smartphone.

Pocket Player 3 - From the developers of a variety of other Pocket PC applications, Conduits has recently released a new version of Pocket Player. Pocket Player 3 supports a variety of features including skins, visualizations and plugins that add support for things like UPnP and Bluetooth Headphones. They also have a plugin SDK kit.
Current Supported Formats: MP3, WMA, WMV, Ogg Vorbis, FLAC, WAV, u-Law, A-Law, AU, and ADPCM WAV. With Plugins: Monkey’s Audio (APE), Musepack
Devices Supported: Windows Mobile 5, Pocket PC 2002\2003 and Smartphone.

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