uandme72,
That clarification was on point! It sounds like you’ve been conducting some great research. So far we know that your Safari browsing history is syncing as expected from the iOS device to your Mac; however, it only syncs from your Mac to the iOS device(s) once you log out and back into iCloud on that device. It sounds like it only refreshes to the present point and any subsequent Safari history on your Mac remains in limbo until you log out again.
Do I have that correct?
If so, did you log out and back into iCloud on all three devices? Logging out of all devices running iCloud, restarting each device, and then logging back into iCloud is the best way to ensure that iCloud is refreshed across the board.
I’m also curious about the devices you’re using. Which iOS model(s) and iOS version(s) are you running? Which Mac and macOS version?
Is it possible that it’s simply taking a little longer to sync to the iOS device? I realize that it doesn’t appear immediately on your iOS device when you visit a page in Safari on your Mac, but if you wait for a period of time, does it eventually appear?
Does it seem to matter whether you’re using Wi-Fi or the cellular data on your iOS device(s)?
I look forward to learning more.
Take care.