Will this copy installed programs such as Office that is on the old hard drive and be copied to the new hard drive and not have to be reinstalled or the OS?

I do not use this for copying individual programs, and do not know if that would work. I use it for cloning entire drives, which it does well. Only problem is that software that comes with it will only clone to an equal or larger drive, so I had to obtain some 3rd party software to clone from a 300GB spinning drive to a 250GB SSD. The clones work with no additional action. The OS all installed applications and all personal files are present on the clone.

If I stick two drives in here at the same time, will they show up on my Mac as two different drives? I currently have a Sabrent dual dock and it only shows one drive at a time.

Yes. They show up as two separate drives. I got this so I could take two drives out of an old Mac and have access to them, at the same time, on a new Mac (both Mac Pro cheese graters). Works like you'd expect.

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User Manual

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Tripp Lite USB 3.0 SuperSpeed to Dual SATA External Hard Drive Docking Station with Cloning for 2.5in/3.5in HDD (U339-002)

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Read and Write to two drives simultaneously
Accepts 2.5" or 3.5" SATA drives up to 4TB
Docking functionality compatible with Windows, MAC, and Linux systems
Compliant with SATA HDD or SSD drives up to SATA III
1-Year Limited Warranty

Overview

Specs

Reviews (15)

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USB 3.0 / USB 2.0 Dual Hard Drive SATA Docking Cloning Station

Model
Brand	Tripp Lite
Model	U339-002

Details
Type	Office Products
Internal Interface	SATA
External Interface	USB 3.0

Dimensions & Weight
Weight	1.55

Package Contents
Package Contents	U339-002 USB 3.0 SuperSpeed to Dual SATA External Hard Drive Docking Station 2.5-ft. USB 3.0 Device Cable External Power Supply with NEMA 1-15P Plug (Input: 100-240V, 50/60Hz, 1.5A; Output:12V, 3A) Owner’s Manual

Additional Information
First Listed on Newegg	February 07, 2014

Warranty & Returns

Warranty, Returns, And Additional Information

Warranty

Limited Warranty period (parts): 1 year
Limited Warranty period (labor): 1 year
Read full details

Return Policies

Return for refund within: 30 days

Return for replacement within: 30 days

This item is covered by Newegg.com's 30-Day Return Policy. Read full return policy for details.

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Tripp Lite USB 3.0 SuperSpeed to Dual SATA External Hard Drive Docking Station with Cloning for 2.5in/3.5in HDD (U339-002)

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Customer Reviews of the Tripp Lite U339-002

Warranty & Returns

Warranty, Returns, And Additional Information

Warranty

Return Policies

Manufacturer Contact Info

Item#: N82E16817404153

Best Sellers

Tripp Lite USB 3.0 SuperSpeed to Dual SATA External Hard Drive Docking Station with Cloning for 2.5in/3.5in HDD (U339-002)

Learn more about the Tripp Lite U339-002

Customer Reviews of the Tripp Lite U339-002

Warranty & Returns

Warranty, Returns, And Additional Information

Warranty

Return Policies

Manufacturer Contact Info