Hooray! This is fixed in the 16.4 beta!
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I recently purchased an iPhone 14 Pro Max and I see a grey square on my lock screen when listening to media on Safari.
Out of the box it was working, then it stopped. Utterly baffling!
It seems like this is due a fix as it’s a key feature to anyone using the navigator.mediaSession.metadata API,
including the web version of Apple Music that also suffers from this bug.