I can't believe I didn't have have an account on MacRumors! Now I do.
First off, my hat off to those who posted here. Dysamoria's fix didn't work for me. Scrumper's did. Thank you both! You really saved me time and a lot of grief as I didn’t know what else to do! And there’s virtually NO other help out there including a pointless phone call to Apple’s Tech Support who also told me that “I’d have to re-install everything OR move to a newer OS version.” These clowns and their corporate scripts!
I run Sierra on my iMac (Retina 5K, 27-inch, 2017) for perhaps the same reasons why many of you still have to stick to these (stable and totally fine) older MacOS’s — compatibility with different needed software. In my case is Adobe which has been a pile of garbage and problems for years! They still, while they charge monthly fees for their "creative suites", have not worked out compatibility issues with the newer MacOS's. I can't even begin to describe the issues and the nonchalance this company is capable of!
My issue started when iMessage on my iMac stopped sending images in a text. Text would go fine but not images. Trying to troubleshoot the issue, I came across a possible fix which was to simply log out of iCloud and from all the accounts (including iMessage), go to the Keychain and unlock and lock it, restart the computer and that’s that! I didn’t change anything, moved files, or did anything else! Once I logged out iCloud from within System Preferences, I could not log back in! It was a “Can’t log in at this time, try later!” message. Days later the same and no fix. I could log into iCloud using any browser directly though. That never changed.
I tried everything. PLISTs delete and restarts. Safe Mode log ins. Nothing worked.
This Apple Intermediate Certificates keychain hack worked! Double clicked on the downloaded certificate, saw it in the Keychain, restarted the computer and it all worked after that!
It’s a nightmare if you run Adobe or some other older creative software (music, design, etc).
Anyway, I hope this thread saves many from going nuts and spending hours trying to troubleshoot.
Thanks again!