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When updating my Mac, I often get a password popup like the following. enter image description here

Why does the keychain not remember my password from the last 100 times I entered it. And why does it not offer me the fingerprint option? I have my Touch ID options set as follows.

enter image description here

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I would suggest you reset the Touch ID completely and add it back again. It can help you to fix the issue.

  1. Restart your Mac and hold down Command+R while it's rebooting to enter Recovery Mode
  2. Launch Terminal.
  3. Enter the following:

    xartutil --erase-all
    
  4. Press Return.

  5. Type Yes when prompted to confirm.
  6. Press Enter.
  7. Quit Terminal.
  8. Restart your Mac in normal mode.
  9. Setup your Touch ID again and it should work.
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  • Is that a serious comment? Sorry, but how can I start a terminal in recovery mode? It gives me several options, but not that one.
    – Jim Newton
    Mar 6, 2020 at 13:50
  • Here is a similar issue for iPhone. iphonehacks.com/2016/08/…
    – Jim Newton
    Mar 6, 2020 at 14:06
  • @JimNewton: Why do you doubt the shared solution? osxdaily.com/2017/12/21/delete-touch-bar-data-mac Check here too.
    – Udhy
    Mar 6, 2020 at 14:09
  • The comment at iphonehacks.com/2016/08/… does not seem to work.
    – Jim Newton
    Mar 6, 2020 at 14:24
  • I just wanted to make sure the shared solution was legit, as when I tried to research it before blindly typing something I don't understand, All its uses that I found are associated with cleaning the system, and wiping all the disks before selling the computer to someone else. I also wonder what Udhy's confidence level is. As other people seem to be reporting the same thing and the general consensus seems to be that this is just an annoying Apple Bug.
    – Jim Newton
    Mar 6, 2020 at 14:25

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