Not so much a Siri issue but an Apple Music gripe nonetheless. I typically play my ‘main playlist’ which has several hundred songs. Sometimes I like to scroll back through the history and listen to a series of songs from the list. Eg. I might be playing song 300 but want to go back to song 275 and hear 275-300 again.
Sounds easy but no, Apple Music plays song 275 then skips straight back to song 300 again, completely ignoring the other songs in history.
In any other music medium - vinyl, cd, dvd, cassette, cartridge etc - it would play all the songs if you skipped back in time. In order to achieve this in Music I have to come out of my playlist then go back into it again, scroll all the way through to ‘song 275’ (rather than a short scroll in history) and then start playing the playlist again.
It’s the little silly things which irritate the most.