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As you know, Windows Server 2008 and Windows Server 2008 R2 are no longer supported on January 14, 2020. Customers need to upgrade Windows Server 2008 and Windows Server 2008 R2 to a newer version of Windows Server or migrate these servers to Microsoft Azure. and get three years of security support for free, giving you more time to upgrade your servers, reinstall your applications, or rebuild your applications. If you want to learn more about how to migrate your servers to Azure, check out the Azure Migration Center. There are several ways to migrate your server applications to a new version of Windows Server. This blog post covers how to upgrade Windows Server 2008 R2 to Windows Server 2019. You can find more information about installing and upgrading Windows Server 2019 at Microsoft Documentation.
Small Business Server 2011 Upgrade Path
To help you with Windows Server upgrades, the Windows Server team created the Windows Server Upgrade Center, which provides step-by-step instructions for upgrading your data center.
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You can perform an in-place upgrade to Windows Server 2019 from Windows Server 2016 and Windows Server 2012 R2. This means that to upgrade from Windows Server 2008 R2 to Windows Server 2019, you will have two successive upgrade processes.
Not all server roles and applications can be migrated to older versions of Windows Server. Read the specific documentation for your operating system scenario, such as upgrading roles in Windows Server 2016. Alternatively, you can also redistribute applications on a fresh installation of Windows Server 2019.
Before you start upgrading your servers in place, make sure you plan your upgrade and make sure you have all the details to avoid any surprises at the end of the migration. The Windows Server Update Center can help you with a checklist that includes, for example, the following:
You should also collect the following system information before starting the upgrade process. You can use the commands below. Please save the results elsewhere.
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I know I’ve mentioned before, make sure you have a backup you can restore to the server you’re performing an in-place upgrade on. Make sure you are aware that the following update processes may take some time.
If your server is connected to the Internet, make sure you click Go Online to install updates now (recommended). This will download the latest updates to the installer.
Enter the Windows Server License Key for Windows Server 2012 R2 if required. If you are not prompted for a license key, you can skip this step.
Select the correct version of Windows Server that you want to install. Make sure you choose a server with a GUI or core server configuration depending on your needs.
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The installation will complete and restart automatically. When the upgrade is complete, you will see the Windows Server 2012 R2 login screen.
After upgrading Windows Server 2012, log in and check if the server has been upgraded. Be sure to test that the application is running as expected and that users can access the application. Make sure your server’s IP settings and firewall still allow clients to access your system.
If there is a problem with the update, backup and zip the %SystemRoot%Panther folder (usually C:WindowsPanther) and contact support.
If everything works as expected, you can install the latest Windows Server 2012 R2 updates and make sure your server is fully configured. Before moving from Windows Server 2012 R2 to Windows Server 2019 upgrade, I also recommend that you create a backup of the server, in which case you won’t lose the work you did from 2008 R2 to 2012 R2.
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If your server is connected to the Internet, be sure to download and install updates, drivers, and optional features (recommended). This will download the latest updates to the installer.
Enter Windows Server License Key for Windows Server 2019 if required. If you are not prompted for a license key, you can skip this step.
Select the correct version of Windows Server that you want to install. Make sure you choose Windows Server 2019 Datacenter (Desktop Experience) or Windows Server 2019 Datacenter (Core) according to your needs.
The installation will complete and restart automatically. When the upgrade is complete, you’ll see the Windows Server 2019 login screen.
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After upgrading Windows Server 2019, log in and check if the server has been upgraded. Be sure to test that the application is running as expected and that users can access the application. Make sure your server’s IP settings and firewall still allow clients to access your system.
If everything works as expected, you can install the latest Windows Server 2019 updates and make sure your server is completely cleaned. I also recommend that you make a backup of the server; then you won’t lose the work you did.
I also highly recommend looking into Windows containers to keep your applications fresh. Watch our full video here on Microsoft Channel 9:
There are many ways to update or migrate your apps, in-place update is just one of them, and it may not always be appropriate. However, in some cases, it is the easiest way to get a new version of Windows Server. I hope this gives you an overview of how to perform in-place upgrades from Windows Server 2008 R2 to Windows Server 2019. If you have any questions or suggestions about the upgrade, please leave a comment below.
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You must be a registered user to add a comment. If you have already registered, log in. Otherwise, register and log in. To request and install an SSL certificate from a trusted CA, for example, for Windows Small Business Server (SBS) 2011, you must use the SBS Console. While you may be tempted to use Microsoft Exchange or IIS to create and install an SSL certificate to secure your SBS site, please don’t. SBS simplifies the SSL certification process and allows you to manage everything through the SBS control panel.
Use the instructions on this page to generate a Certificate Signing Request (CSR) and then install your SSL certificate.
These instructions assume that you have enabled the Certificate Authority snap-in and the Certificate snap-in in the Microsoft Management Console (MMC). This guide also assumes you have your email address set up. For more information about the snap-in and setting up your email address, see Small Business Server (SBS) 2011 from Microsoft.
If you have not yet created a Certificate Signing Request (CSR) and issued your certificate, see Small Business Server 2011: Create Your CSR (Certificate Signing Request).
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If you used something other than the SBS Console to generate the CSR for your SSL certificate and you’re having trouble installing your certificate, you should do the following:
If your website is publicly accessible, the ® SSL Setup Diagnostic Tool can help you diagnose common problems. That’s why many small businesses adopted the Windows Small Business Server (SBS) product – now that the product has been discontinued, these organizations tend to need a little more. further instructions on the transfer route from SBS 2003, 2008 or 2011.
With the ability to move most SBS Server functions such as email and file sharing to Office 365 with Exchange Online, SharePoint Online and OneDrive for Business, many small businesses question whether an on-premises server is still necessary.
I usually recommend having an in-house server, yes, even with Office 365. But in very small offices, you
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Instead, just go with a hosted installation of Windows Server Essentials in the Microsoft Azure cloud. Either way, I see a hybrid setup of Windows Server + Office 365 as the gold standard in the near future. Here’s why:
For all these reasons and more, Windows Server still has a place in the small business network. The good news is that hardware is very cheap these days, and most small businesses will be able to offload the majority of their data footprint to the cloud, meaning that hardware requirements have likely decreased since the last upgrade cycle.
Version (not Essentials), enables the Hyper-V role and sets up a Windows Server Standard virtual machine that “stands in” as your server for SBS. Optionally, you can enable it
Role, if you are interested in any of the features it includes such as PC client support, remote web access, etc. Here is a brief summary of the two implementation options:
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If yes to any of the above, go with Standard. Alternatively, if you’re sure the answer is no, you can stick with Essentials.
Users and devices for which you have enough CALs, but Experience Essentials features will only support 500 users / 500 devices in 2016 (up from 100/200 in 2012 R2).
Another capability offered by Standard is the ability to join an Essentials computer as a member server, without promoting it to a domain controller role – perhaps less of a concern for some organizations. Of course, you can also choose to convert to a standard license along the way.
This is the best resource I know of for comparing different Office 365 plans and