Repeated requests for keychain login password

Tell it to always use the Keychain.

When you allow once, it will repeat asking you to allow.

You can also clear the keychains in the Keychain Access utility for Microsoft, and try logging in your Microsoft application again.

The best thing to do is clear the Microsoft keychains and rebuild them by logging back in your Microsoft account.

Use the Keychain Access utility in Applications -> Utilities to do so.