Artie I wonder if you are running into one of the new security provisions built into MacOS 10.13 and iOS 11? Perhaps one we are not cognizant of or one we do not yet fully comprehend all of its implications?

Just to be sure I am following correctly
  • When you say, "my keychain", are you referring to the Login, iCloud, or System keychain?
  • Do you have iCloud Keychain activated?

If we knew what it was we were doing, it wouldn't be called research, would it?

— Albert Einstein