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I've recently set up a yubikey to login into my laptop, and while doing that I've also changed my account password, so that my default password is pretty long and I can use the yubikey plus a pin to login. It works fine, sometimes it doesn't pickup the USB key, but mostly works.

The really annoying issue I have though is that I somehow broke the keychain. So now when I login with the yubikey I get a window like this:

enter image description here

The original message is macOS wants to use the "login" keychain, but I also get this message when I first log in to 1password, or, surprisingly enough when I use preview...

I've seen already a couple of posts here, but none of them were helpful to fix this issue.

I've tried to delete the keychain but it didn't work as well, not sure if I did it correctly.

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The keychain may still be using the old password. In order for the act of logging in to unlock your keychain the two (user account and login.keychain) need the same password. I would recommend turning off in Keychain Access the settings that will prompt you to enter your long password. With your login keychain selected on the left, under the Edit menu select "Change Settings for keychain login" and uncheck both boxes.

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  • The checkboxes are already unchecked: s.patrick.wtf/wRiH9Kc14a I've noticed that I only get the popup when I log in with my yubikey, so probably the yubikey is not unlocking the keychain
    – patrick
    Commented Sep 25, 2017 at 15:35

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