Login Items keychain popup bug

[patent10021]

I'm writing this summary just to clarify it for myself in my head and for others. You can tell me if any of the info I am assuming is incorrect.

There are login, iCloud and System, and System Roots keychains. I'm thinking keychains are like profiles really. Then then you have categories like passwords, certificates, my certificates, keys.

The login keychain has its own passwords (Handoff, Apple IDs etc) and keys.
The iCloud keychain has its own passwords (watch, iPhone etc).
The System keychain has its own passwords (WiFi etc), keys and certificates (Apple Developer etc).
The System Roots keychain basically only has a certificates category (ecommerce Verisign certificates etc).

Issue

Recently I have been getting a popup from Node.js wanting me to enter in my Login Items keychain password. This happens every day. I enter in what I think is a correct password and a day later it happens again. I searched everywhere and basically there is no fix except for the usual process of deleting the keychains folder and creating a new login etc.

Because of this I decided to change my password for keychain "login" [Edit -> Change Password for Keychain "login"] because I thought this would help. I changed it and used that password the next time the popup came back. The new password was accepted but the popup persists.

What should I do? If I delete a keychain which keychain should I delete? Can you only delete all or none? Do I have to enter in all my passwords for 500 web sites again? How does it affect iPhone<->Macbook password syncing? How will it affect creation of p12 files using a previous certificate?

 

[hobowankenobi]

Using the Keychain Access tool, determine which keychain item is associated with the request in question, and delete it. Once gone, you will get prompted for the PW once, and you should be allowed to save it, thus creating a new keychain entry. I would start with login/passwords.

If you double click on the line items they open, and you can check the Attributes and Access Control for info about the keychain item. And, if you check the show PW option, you can see the PW, which could be a good clue as to what account it is associated with, as well. Creation and modified dates are clues too.

Before you consider any changes, you can copy your keychain items to save duplicates. Just name them something else (like add: backup to the name), so if you do butcher/break something, all you have to do is rename the duplicates.

Typically you don't have to delete the entire keychain. You can, but that is the sledge hammer approach. Also, if deleted, a new one is generated automatically at login, just like a brand new user account would. No need to make one.