I have a MacBook Pro (17-inch, Early 2009) 8GB Memory at 2.93 GHz, Model A1297. I just purchased a new MacBook Pro 2.93 GHz 6-core intel Core i9, 32GB, A1990. I have tried numerous ways to connect with Target Mode using a NEW Anker PowerLine USB-

Target Disk Mode requires a bona-fide ThunderBolt Port. Your 2009 model does not have a ThunderBolt port.

USB connection is not supported.

macOS Sierra: Transfer files between two computers using target disk mode

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You would think your cable/ USB3 would be backwards compatible with your USB2 port.

If it is convenient I would ask for help over the counter at the Apple store.

Genius reservation http://www.apple.com/retail/geniusbar/

Target Disk Mode requires a Firewire port (there is one on his old Mac). If he purchases a USB-C to Firewire adapter for his new MacBook Pro, he should be able to use Target Disk Mode.

https://www.apple.com/shop/product/MMEL2AM/A/thunderbolt-3-usb-c-to-thunderbolt- 2-adapter?afid=p238%7CsEc33DURg-dc_mtid_1870765e38482_pcrid_246386725857_&cid=ao s-us-kwgo-pla-btb--slid--product-MMEL2AM/A