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Can install from terminal into Raspberry Pi PC Desktop from Parallels 18. Mac Folder to Raspberry Pi works. Clip board sharing does not seem to...
Pure speculation-- WebUpdater may need tighter serial port control than available through the WebUpdater, Windows, Parallels, Serialclient, Mac OS...
What worked for me -- eTrex Vista 3.70 & 3.80 firmware Mac OS X 10.4.11 (Tiger) Parallels 3 build 5600 Windows XP SP2 USB Serial Radio Shack...