How do I add multiple songs to an existing playlist from the (no longer called) Library? Highlighting multiple songs and clicking the "Add to" button will only add the with the little arrow, not all the highlighted ones!

How do I add multiple songs to an existing playlist from the (no longer called) Library? Highlighting multiple songs and clicking the "Add to" button will only add the one with the little arrow, not all the highlighted ones! I am using the "new" iTunes.

For the moment there isn't a way for us end-users to control what is "matched" or "uploaded." That is purely a result of Apple's server-side algorithms.
To re-add multiple songs at once simply highlight all the songs you want to re-add, then right-click (or Control+click) the list and choose "add to iCloud."

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