You cannot play them directly. First you need to extract individual DSD tracks. What goes then depends on your DAC - yes you have to use external DAC since none of Squeezeboxes can play DSD natively. I am not familiar with Apple environment. I use Foobar200 in Windows (or Wine under Linux) for all file conversions. This is not a plug and play process, but it does not takes much time either. Generally you need DAC yhat supports DoP either via spdif or USB. Then you need extended output plugin for Squeezebox. Foobar2000 can convert DSD files onto DoP files, which Squeezebox sends to DAC like any regular PCM (flac, wav etc.) file.
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