Keith Riggle wrote:
"Automatically sync when this iPhone is connected" doesn't always work on macOS Tahoe with iPhone running iOS 26 connected via USB
Apple suggests connecting DIRECTLY to the Mac to sync an iPhone. You aren't doing that. I don't know how often you need to sync the iPhone. If it's not very often, why not simply unmount a drive that is using one of your Mac ports so you can connect the iPhone directly as Apple instructs.
Any suggestions on how to get it to work consistently ...
Look into getting a hub that works properly.
I have been using OWC Thunderbolt hubs for some years now, both for my work and personal Macs (these are Macbook Pros). I typically will have two or three external drives connected through those OWC hubs and have never had to connect them directly to the Macs. I avoid connecting drives directly to the Mac because that would mean constantly having to unplug them when taking the laptop somewhere. The hub makes this much easier, and OWC also provides a little utility called OWC Dock Ejector that when clicked simply dismounts properly all the drives that are connected via the hub, so one can take the laptop for portable use. The Macs (and presumably the drives) periodically sleep and wake up with no issues. This leaves other ports on the Mac available for other things, including iPhone syncs. That said, I have also synced my iPhone through these OWC hubs. Never with any issues. A properly designed hub will being able to host multiple drives and sync the iPhone as well, although I do usually follow Apple's guidance on syncing the iPhone through a direct cable. l
Just another example of an Apple feature that does not work as advertised.
Except you didn't follow Apple's guidance on using a direct connection for the iPhone sync. And your hub is clearly not fully compatible with macOS, what hub are you using.
I use the ports on my Mac for important external drives, which obviously don't work as well through the hub.
That sounds odd. My ancient Thunderbolt 3 hub provides 40 Gbps. You need a modern hub, I think. OWC's Thunderbolt 4 hub provides three 40 Gbps ports. The Thunderbolt 5 version provides 80 Gbps. These OWC hubs also provide pass through charging (140W for the latest version). You can connect everything via these hubs using just one Mac port. The OWC Dock Ejector menu item provides a one click orderly dismount of all connected drives in one click. Disconnect one cable and you can take the laptop off for portable use.