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Yes, you must first convert the GCD to an RGN then flash with Updater.exe in preboot mode. But because the device is showing "loading" message after "system software missing" it likely has a corrupt gupdate.gcd in its .System folder so you may need to load 'cure' fw to re-enable Mass Storage Mode so it can be deleted. See: [Only registered and activated users can see links. ], in particular read all of the initial post there and if you need further explanation read this too: [Only registered and activated users can see links. ].

When it's showing in Device Manager under "GARMIM Devices", it's in preboot mode.