start over with keychain

Hello,

If you are talking about the pop-up to enter your Keychain password you may be able to modify a setting to return it to normal operation.

If your Mac keeps asking for your keychain password - Apple Support

"If your Mac keeps asking for your keychain password

Your keychain may be locked automatically if your computer has been inactive for a period of time or your user password and keychain password are out of sync.You can set a length of time that Keychain Access waits before automatically requiring you to enter your password again.

1. In the Keychain Access app  on your Mac, click “login” in the Keychains list.
2. Choose Edit > Change Settings for Keychain “login.”
3. Select the “Lock after” checkbox, then enter a number of minutes.
4. If you want to require a password each time the computer goes to sleep, select the “Lock when sleeping” checkbox.
5. Click Save."

If you do decide to go with the option of starting over (I don't believe this would fix anything with pop-ups) you can do this in your Keychain Access settings. With Keychain Access open, click Keychain Access in the menu bar then Settings.

I hope this helps.

When you login to macOS, the login keychain is automatically unlocked using your Mac user password. The login keychain contains all your saved passwords among other secure items like certificates, keys and secure notes.

If you changed the password, you may have done so in such a way as the login keychain has the old previous password. When you login to macOS the keychain is locked and fails to unlock because the passwords do not match. You will then see one prompt after another for every single saved password you have in your keychain. It's a very annoying scenario. You end up failing to get past it, click cancel many dozens of times and minutes later it starts over again.

You'll need to enter the previous password and then the keychain will unlock and the password will be updated to the new one on the keychain automatically. Then reboot and it should resolve the problem. The keychain is normally unlocked as soon as you login.

The other suggestion about resetting the keychain will also work but that just creates a new keychain after it renames the old one in ~/Library/Keychains. This is a nuclear last resort option. Hopefully you'll remember the previous password. It would be possible to import that old keychain if you can remember the password. There is no way to reset a keychain password.

If this is a work computer, ask your IT department about Apple Kerberos Single Sign-on extension, NoMAD or JAMF Connect. These tools help solve problems with changing passwords on Macs in work environments managed by an IT department. This is a very common issue in work environments. The tools typically provide an menu-bar icon with the number of days till expiration and if you click that menu and then change password, it will ensure the password change is made on the Mac, in the keychain and the FileVault pre-boot authentication login so all the passwords are in sync. The tools also help with single-sign-on to company resources such as web apps, etc. If the help desk reset your password, it will let you know the password changed and offer to help you change the password on the Mac.