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I have a 16", MacBookPro with 4, USB-C ports.

I also have a 27", Cinema Display with a USB-Type A (audio), MiniDisplay (video), and MagSafe power connectors. At the rear, it has three, USB-Type A ports.

Currently, I use a ULTRADRIVE Kit USB-C™ Multi-Display Modular Dock to connect the monitor to the computer.

I'd like to connect a second, 27" Cinema Display to my laptop. It appears that there is a newer model (https://support.apple.com/kb/SP642?locale=en_US) that has more connectivity options.

I'd like to know if I can "daisy chain" the older, 27" monitor, to the "newer" 27" monitor, then connect it to the computer, using this adapter. Put another way, will this architecture work? Will both monitors run at their highest resolution rates? Will the power, supplied directly to the "newer" monitor be passed to the older monitor and the computer?

I know there are a number of other questions that appear to be similar, but none answer my specific questions.

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No, this combination will not work.

  1. The Apple Thunderbolt Display (i.e. "the newer model Cinema Display) works only via Thunderbolt (which your Ultradrive does not offer). To connec the Thunderbolt display you have to use a Thunderbolt 3 to Thunderbolt 2 adapter (and connect it directly to your Mac or a Hub/Dock that support Thunderbolt).
  2. While 2 Thunderbolt Displays can be daisy-chained, you cannot daisy-chain a Cinema Display directly to a Thunderbolt Display (workarounds exists where a Dock is placed in between (MacBook > TB3/2 Adapter > TB Display > Dock/Hub > Cinema Display))

If you require a One-Cable solution you would need a Dock that connects to your MacBook via Thunderbolt 3 and offers:

  • 1 Thunderbolt Port
  • 1 Video Out Port (preferably Mini-DisplayPort)
  • Any other ports you need that are not already covered by the Displays integrated hub.
  • Power Delivery for charing your MacBook

There are multiple Docks that offer these features (OWC, Belkin, CalDigit being amoth the most popular) but they are typically pricier than USB-C solutions without Thunderbolt support.

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