A sad face, not for the software, but for the self who last used it — before the updates, before the loss, before everything started looking forward whether he was ready or not.
It sounds like you're describing a moment or an image: someone looking at a piece (maybe a piece of art, a puzzle piece, a piece of writing, or a fragment of something) that says "StartIsBack" — perhaps the Windows Start menu restoration tool — and reacting with a sad face. startisback sad face
He stares at the screen — the old Start menu, resurrected. StartIsBack. A patch, a prayer, a piece of a past he thought he’d buried. A sad face, not for the software, but