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try-restart returns as soon as middlewared is READY, and middlewared then brings docker up — docker.configure_nvidia merges the stock nvidia sysext over /usr at that point, detaching the overlay after the patched modules have already been imported. Checking the disk there reports "missing" on a perfectly healthy system, and the retry that followed would restart a correctly-patched middlewared straight back into the same race, then log ERROR when nothing was wrong. The disk is the right oracle before the restart and the wrong one after it. After the restart the overlay is re-mounted so the next restart finds patched files, and whether this middlewared actually holds the patch is left to the in-process alert, which is the only thing that can answer it exactly.