It sounds as an issue either with the Keychain App. Try repairing it. To do so just: • Locate the Keychain Access application, under /Applications/Utilities. • Choose Keychain Access > Keychain First Aid. • Enter your User name and Password.
Keychain as you may be aware by now is the main system OSX uses to store your passwords. Anything you ask to be stored is sent to the keychain. Therefore if you choose not to save any passwords you will be asked to enter the password in every time it is required, which is what the keychain is designed to do. The OS X operating system comes with its own password-management utility program called Keychain Access that stores your account names and accompanying passwords for file servers, programs.
• Select Verify and click Start. • If any problems were found, select Repair and click Start again. It could be, too, that you've changed your account password without using the Accounts Preferences pane.
If that is the case, for your default keychain to be unlocked automatically when logged in, you'll have to Synchronize your Keychain Access and login passwords. To do so just: • Open Keychain Access.
• From the Edit menu, choose Change Password for Keychain 'login.' • Type the former password of the account that you are currently logged in to, then click OK.
• If you entered the correct password, a new window appears; enter the original password again in the Current Password field. • In the New Password field, type the password that matches your current account password. • Re-enter the newer password in the Verify field, then click OK. This is needed because, as Apple If you change your account's password using your Mac OS X Install disc (or if your network-based account password is changed due to a network admin forcing a password change), your default keychain password (which uses the same initial password as your user account) does not change. Because of this, you will be prompted to enter a keychain password each time an application requires authentication that your keychain would normally provide. I had the same problem. It has bothered me for several weeks on my new Mac.
It should be caused by changing Mac password using 3rd party software. Mac os x release dates. On macOS El Capitan and Sierra, there is no Keychain Access > Keychain First Aid. Changing login keychain's password does not help. To solve this problem, you have to reset your default keychain. • Open Keychain Access, which is in the Utilities folder of your Applications folder. • Choose Preferences from the Keychain Access menu (or Cmd,), then click the Reset My Default Keychain button in the preferences window. After you enter your new password (same to the password of your Mac account), Keychain Access creates an empty login keychain with no password.
Click OK to confirm. (If you don't see a Reset My Default keychain button, close the preferences window and select the “login” keychain from the left side of the Keychain Access window. Press the Delete key, then click Delete References.) • Choose Log Out from the Apple menu to return to the login screen. • Log in to your account.
Your account password and login keychain password now match. There is a bug that is affecting some users which is related to this. You may see the colour wheel of death when you get the certificate trust prompt from some applications, like Microsoft Remove Desktop of Microsoft Office (weird but it happened only with these to me!) Once you see the colour wheel, your only change is to reboot and after this you will get several prompts for keychain password BUT you would have to type your old password even if you previously reconfigured Keychain Access to use the same password. I will give lots of beers to the one that solves this issue, it drives me crazy!
I came across this same issue on El Capitan, and had already searched and tried all suggestions on here. My solution was to disable FileVault under System Settings > Security & Privacy and everything works fine again. Update: Before you downvote because you can't understand how someone can disable the default FileVault encryption: I don't see the downside of disabling FileVault.