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I installed Sierra last night and my Microsoft Wireless Comfort keyboard suddenly started requiring me to press CapsLock two times in order for it to activate caps lock.

I plugged in an Apple keyboard to test, and that still works as intended.

Is there a setting that I'm missing?

  • If the Apple keyboard works as intended then the problem is probably with the MS keyboard. Do they have any updated drivers or similar issues on their support site? – fsb Sep 21 '16 at 16:49
  • Confirmed this happening on my MacMini with the Ergonomic 4000 keyboard. More needless tinkering on Apple's part, no doubt. – Joshua Pech Sep 21 '16 at 21:14
  • So... I just restarted the iMac and it started working. I have IntelliType 8.2 installed (same as before).. My media keys also started working after restarting. Have you restarted after the Sierra install @JoshuaPech? – thatjuan Sep 21 '16 at 21:21
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Installing IntelliType for your Mircosoft Confort Keyboard Ergo 4000 on macOS X 10.11 (El Capitan) or later will not work. Microsoft didn't update their driver in a while (since 10.7) and didn't sign the extension as they should have done for it to work with the latest versions of macOS.

You could eventually deactivate the security features, but I don't think it worth taking this risk for a keyboard driver. The keyboard works fine without driver, only missing the "Favorites" buttons.

If you really want to customize the "Favorites" shortcut buttons, ControllerMate seems to be a great driver with a great mapping that makes them easily customizable. It is up-to-date and compatible with macOS 10.14 Mojave.

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