16/44 vs 24/96. Which sounds better in streaming ?

I don't see any problem upsampling/oversampling a16/44.1 recording to 24/88.2, 24/176.4, or DSD, as long as it is done properly, which should be easy to do for anyone involved in production. Upsampling to 24/48 or 24/192, OTOH, requires transcoding, which should be avoided where possible because it requires interpolation.

From my personal testing, hi-rez beats 16/44.1, if it is from the same master and well implemented. Unfortunately, a lot of the higher resolution recordings have been remastered. Remastering can be an improvement, but too frequently it's a change for the worse.
 
I think in general, if both files/streams are from the same master and the original was in 24/96 and the 16/44 is a downconverted version, the 24/96 should sound better.

However, there are simply too many variables in digital audio (or audio in general). For example, if your streamer is noisy, you could potentially be feeding more noise from the 24/96 track to the DAC compared to the 16/44 track in which case, you're going to get a leaner and more artificial sound with 24/96. It is also possible that a different filter was selected for 16/44 vs 24/96 within the DAC, in which case, you're just hearing that the DAC filter used for 24/96 sounds worse than the DAC filter used for 16/44. I doubt the latter is the case here but you never know. Some DACs store the filter choice based on whether a track is 44kHz vs 96kHz whereas other DACs would always use the same filter you last selected for all tracks.

Ultimately, I think people should just listen to what sounds good to them. Diving into the technical details and reasoning probably don't contribute much to the enjoyment of this hobby anyway.
 

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