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They did carry over into the USB era! I specifically remember my stepdads copy of Cubase (music production software) requiring a USB dongle to open.
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Ditto - and there's also the "iLok" dongle used by loads of virtual instrument & effects plugins for DAWs.
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I could have sworn, back in my day, on WinNT4 we successfully chained a red and white pair from Autodesk. One for AutoCad, and either Mechanical Desktop or 3ds Max.
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It worked sometimes, but was always a roll of the dice.
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