A system for processing DRM-enabled files includes a playback device and a software module. The software module includes a license-downloading module, a license-transforming module, a decryption module and an encryption module. The license-downloading module is configured to download a first license from a license server to a computer. The license-transforming module is configured to convert the first license to a second license. The decryption module is configured to decrypt a first DRM-enabled file of the computer into a raw file with a first decryption key. The encryption module is configured to encrypt the raw file into a second DRM-enabled file with a second encryption key. The playback device is configured to decrypt the second DRM-enabled file with the second license. The method of the system is also provided.