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I use iTunes on the desktop, but I’ve only ever had it happen when I’ve been listening to music on my phone a minute or two prior. I’ve never logged out on either and if it was outside the few-minute window I was never prompted with that popup. Sorry it didn’t work for you, and that would probably be a dealbreaker for me, but fortunately that’s not something I run into.
I use iTunes on the desktop, but I’ve only ever had it happen when I’ve been listening to music on my phone a minute or two prior. I’ve never logged out on either and if it was outside the few-minute window I was never prompted with that popup. Sorry it didn’t work for you, and that would probably be a dealbreaker for me, but fortunately that’s not something I run into.