What do I do when my "Require password after sleep..." is UNCHECKED, but my computer still requires me to enter my password after startup or sleep? I tried to CHECK the "Require password..." checkbox, but it won't even let me click it on. It isn't grayed out, it just simply doesn't check it when I click on it.
To find out if it's system wide or user specific, try this...
Open System Preferences>Users & Groups, unlock the lock, click on the little plus icon, make a new admin account, log out & into the new account.
Does it work in the new account?
Both the "Lock after..." and "Lock when sleeping" were already unselected :(.
I made a new admin account. Within that new account, I was able to toggle the "Require Password" box on and off, however, the new profile still made me put a password in, even after I had unchecked the box. Now both the original profile, and the new profile are requiring a password, even though the "Require Password" box is unchecked. {I'm trying to be able to log into my computer without requiring a password}.
Accountsd asking you often…
Just open the "Keychain Access", click right on the "login" keychain in the sidebar, select "Change settings for Keychain "login"" and unselect both options "Lock after ..." and "Lock when sleeping". – Tom Kraina Sep 8 '16 at 10:55
If your Mac keeps asking for the login keychain password
The password of your macOS user account might not match the password of your login keychain. Either create a new login keychain or update it with your new password.
It might Require reinstalling the OS.
Require password checkbox not working
