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The rain fell in steady, gray sheets against the window of the small apartment in Seattle. Inside, a 2014 MacBook Air sat open on a worn wooden desk, its screen glowing softly. The operating system was macOS Big Sur 11.7.10—a final, frozen version, unsupported for upgrades but still faithfully running.

If you need to manage an older iPod or manually install an older version of iTunes, see the Special Cases section below.

Use a virtual machine (e.g., VMware, VirtualBox) running macOS Mojave (10.14) or Windows with iTunes.