How to Migrate Windows Server 2008 (R2) to 2016/2019 Step by Step

How to migrate Windows Server 2008 to 2016 step by step? This tutorial shows you the easiest and quickest way to transfer data, applications, and user account from Windows Server 2008 to Windows Server 2016 by EaseUS Todo PCTrans in a few clicks. Read on and find out how.

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When we talk about how to migrate Windows Server 2008 to 2016 step by step, it usually refers to two requirements: one is to upgrade Windows Server system from 2008 R2 to 2016, and the other is migrate data and files from Windows Server 2008 to 2016 directly. You can check the complete guide to upgrade Windows Server 2008 R2 to 2016, including the migration of the Active Directory (AD) environment, Domain Naming System (DNS) and Dynamic Host Configuration Protocol (DHCP).  

In this article, we mainly focus on how to migrate data, applications, or user account from Windows Server 2008 to 2016 with an easy Windows data transfer tool. 

EaseUS Todo PCTrans - The Ultimate Windows Data Transfer Tool

EaseUS Todo PCTrans is one of the best Windows data transfer applications for files, applications, user accounts, and settings sharing between two Windows PCs or Windows Servers. For Windows Server migration, it has the following key features.


For all Windows Server data copying

It supports data, program, user profiles and settings migration between Windows Servers in one-click without data loss. 


Simple solution and interface

The graphical user interface makes it intuitive to transfer data in simple clicks. Both computer experts and beginners can get started quickly.


3 flexible transfer modes

You can choose the mode of transmission according to your actual needs, transfer via PC to PC, locally, or via backup files.


Full support for Windows Server

It's compatible with all Windows Server versions, including Windows Server 2019, 2016, 2012, 2008, and 2003.


How to Migrate Windows Server 2008 to 2016 Step by Step

You can learn from the following instructions on how to migrate Windows Server 2008 to 2016, including transfer files over the network (on the same LAN) and migrate data using backup files offline. First, click the button below to install EaseUS Todo PCTrans on your computer if you haven't installed it yet.

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Migrate Windows Server 2008 to 2016 via Network Connection

Connect your two Windows Server computers on the same LAN and transfer files, and apps with account settings through the network.

Step 1. Launch EaseUS Todo PCTrans on your source and target computers, connect both PCs via the internet.

1. At the "PC to PC" section, choose the transfer direction and click "Start" to continue. 

select pc to pc

2. Select your target computer via its device name, then enter its account password or verification code. Then click "Connect" to continue.

You can check the verification code on the right top of "PC to PC" mainscreen on the target computer.

connect the two pcs

Step 2. Select the categories Applications, Files, and Accounts to transfer via the internet.

If you want to transfer data selectively, click "Edit" under each category, and choose the specific items.

select applications, files or accounts

Step 3. Click "Transfer" to start transferring your apps/files/accounts from one computer to another computer via the Internet.

transfer applications, files or accounts via internet

Also read: How to share files between two laptops using WiFi in Windows 10 

Transfer Data from Windows Server 2008 to 2016 via Backup Files

This "Backup & Restore" tool is free of charge and enables you to create backups of your files, programs & accounts on the Windows Server 2008 and then restore and move them to the Windows Server 2016 or 2019.

Step 1. Create a backup file. 

1. Connect your USB (flash) drive/external hard drive to your source computer. Launch Todo PCTrans, click "Backup & Restore > Start" on the main screen.

Transfer files via backup and restore - step 1

2. Select "Data Backup" to move on.

Transfer files via backup & restore - step 2

3. Hover over "Applications", "Files" and "Accounts" columns to choose the specific data, applications, etc., and click "Back up" to create a backup file. 

Transfer files via backup and restore - step 3

Step 2. Recover via the created backup file.

1. Plugin your USB drive which stores the created backup file to the target PC.

Ensure your target PC has EaseUS Todo PCTrans, open PCTransImage and double-click the backup file. Otherwise, click PCTrans_setup.exe to install this tool.

Transfer files from PC to PC via backup & restore - step 1

2. Now, you can select Applications/Files/Accounts you want to restore. Click "Restore".

Transfer files from via image - step 2

3. Wait a while and click "OK" to finish the restore process.

Transfer files via image - step 3


To migrate from old Windows Server 2003 or 2008 to new Windows Server 2012, 2016, or 2019, EaseUS Todo PCTrans provides you with one-stop solutions to copy files, applications, as well as other indispensable data, which are as simple as a click away. If you don't know how to migrate data between two Windows Servers or how to do it effortlessly, be sure to try this tool out.

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Migrate Windows Server 2008 to 2016 FAQs

Check the following frequently asked questions on Windows Server 2008 to 2016 migration.

1. Can Windows Server 2008 be upgraded to 2016?

You can't upgrade Windows Server 2008 to 2016 directly unless performing a clean installation. If you want to complete an in-place upgrade, you need to first upgrade from Windows Server 2008 to 2012, and then upgrade to 2016.

2. How do I move DHCP from 2008 to 2016?

How to migrate DHCP from Windows Server 2008 to 2012/2016:

  • Log on to the old/existing DHCP server.
  • Open the Command Prompt and run as Administrator.
  • On the Action menu (from within the DHCP management console), click "Backup".
  • In CMD, type netsh dhcp server export C:\Users\\Desktop\dhcp.txt all, and then press ENTER.
  • Install the DHCP role on the new (2012/2016) DHCP server using the Server Manager.
  • Copy the exported DHCP text file to the desktop of the new DHCP server.
  • Make sure that the DHCP service is installed and started on the new DHCP server.
  • Open the command prompt as Administrator (on the new server)
  • Type netsh dhcp server import C:\Users\\Desktop\dhcp.txt all, and then press ENTER
  • Open the DHCP management console on the new server.
  • In the console tree, right-click DHCP and select "Authorize".

3. Can Windows Server 2012 be upgraded to 2016?

You can only upgrade Windows Server 2012 to Server 2016. You can’t skip the upgrade, which means you're going to need to plan ahead for a more substantial upgrade, like you can't upgrade Windows Server 2012 Standard edition to Windows Server 2016 Datacenter edition.

4. Can Windows Server 2008 be upgraded to 2012?

Yes, you can upgrade Windows server 2008 R2 Enterprise to Windows Server 2012 Datacenter. After upgrading, you can log in to the server and check for the edition. Click on "Server Manager", then "Local Server", and check the properties of the server. You a see the operating system version is Microsoft Windows Server 2012 Datacenter.  

About the Author

Updated by Sherly

Sherly joined EaseUS in 2022 and she has always loved writing articles and enjoys the fun they bring. She receives professional training here, focusing on product performance and other relative knowledge. She has written over 200 articles to help people overcome computing issues.

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Written by Cedric

Cedric Grantham is a senior editor and data recovery specialist of EaseUS. He mainly writes articles and how-to tips about data recovery on PC and Mac. He has handled 10,000+ data recovery cases and is good at data recovery of NTFS, FAT (FAT32 and ExFAT) file systems, and RAID structure reorganization.

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Reviews and Awards

Product Reviews

TrustScore 4.7 | 34 reviews
  • EaseUS Todo PCTrans Free is a useful and and reliable software solution created to serve in computer migration operations, be it from one machine to another or from an earlier version of your OS to a newer one.

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  • EaseUS Todo PCTrans is by the folks at EaseUS who make incredible tools that let you manage your backups and recover your dead hard disks. While it is not an official tool, EaseUS has a reputation for being very good with their software and code.

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  • It offers the ability to move your entire user account from your old computer, meaning everything is quickly migrated. You still get to keep your Windows installation (and the relevant drivers for your new PC), but you also get all your apps, settings, preferences, images, documents and other important data.

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How to Migrate Windows Server 2008 (R2) to 2016/2019 Step by Step

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