June 13, 2023—KB5027275 (Monthly Rollup)
Release Date:
6/13/2023
Version:
Monthly Rollup
IMPORTANT As of January 10, 2023, Microsoft no longer provides security updates or technical support for Windows 7 Service Pack 1 (SP1). For customers who need additional time to upgrade and modernize their devices running Windows Server 2008 R2 on Azure, we offer one additional year of Extended Security Updates on Azure only, beginning on February 14, 2023 and ending on January 9, 2024. This also applies to Azure Stack HCI, Azure Stack Hub, and other Azure products.
We recommend that you upgrade to a later version of Windows Server.
Upgrade to Windows 10: FAQ Learn more about upgrading Windows Server
Summary
Learn more about this cumulative security update, including improvements, any known issues, and how to get the update.
REMINDER Windows Server 2008 R2, Windows Embedded Standard 7, and Windows Embedded POS Ready 7 have reached the end of mainstream support and are now in extended security update (ESU) support. Windows Thin PC has reached the end of mainstream support; however, ESU support is not available.
As of July 2020, optional non-security releases for this operating system are no longer offered. Operating systems in extended support have only cumulative monthly security updates.
Verify that you have installed the required updates in the How to get this update section before installing this update.
Windows Server 2008 R2 Extended Security Updates third and final year of ESU ended on January 10, 2023. Many customers are taking advantage of Azures commitment to security and compliance and have moved to Azure to protect their Windows Server 2008 R2 workloads with free Extended Security Updates.
For customers who need additional time to upgrade and modernize their devices running Windows Server 2008 R2 on Azure, we offer one additional year of Extended Security Updates on Azure only, beginning February 14, 2023 and ending on January 9, 2024. This also applies to Azure Stack HCI, Azure Stack Hub, and other Azure products.
Customers who get the additional fourth year of free extended security updates (ESUs) must follow the procedures in KB4522133 to continue receiving security updates after extended support ended on January 10, 2023. For more information about ESU and which editions are supported, see KB4497181.
The steps to install, activate, and deploy ESUs remain the same. For more information, see Obtaining Extended Security Updates for eligible Windows devices for the Volume Licensing process. For embedded devices, contact your original equipment manufacturer (OEM). For more information, see the ESU blog.
Improvements
This cumulative security update contains improvements that are part of update KB5026413 (released May 9, 2023). This update also contains miscellaneous security improvements to internal Windows OS functionality. No specific issues are documented for this release.
For more information about the resolved security vulnerabilities, please refer to the Deployments | Security Update Guide and the June 2023 Security Updates.
Known issues in this update
| Symptom | Next step |
| After installing this update and restarting your device, you might receive the error, “Failure to configure Windows updates. Reverting Changes. Do not turn off your computer”, and the update might show as Failed in Update History. | This is expected in the following circumstances:
If you have an ESU key and have encountered this issue, please verify you have applied all prerequisites and that your key is activated. For information on activation, please see this blog post. For information on the prerequisites, see the How to get this update section of this article. |
How to get this update
Before installing this update
IMPORTANT Customers who get an additional fourth year of free extended security updates (ESUs) only on Azure for versions of these operating systems must follow the procedures in KB4522133 to continue receiving security updates. Extended support ended as follows:
- For Windows 7 Service Pack 1, extended support ended on January 14, 2020. Extended Security update (ESU) ended on January 10, 2023.
- For Windows Server 2008 R2 Service Pack 1, extended support ended on January 14, 2020.
- For Windows Embedded Standard 7, extended support ended on October 13, 2020.
- For Windows Embedded POS Ready 7, extended support ended on October 12, 2021.
- For Windows Thin PC, extended support ended on October 12, 2021. Note that ESU support is not available for Windows Thin PC.
For more information about ESU and which editions are supported, see KB4497181.
Note For Windows Embedded Standard 7, Windows Management Instrumentation (WMI) must be enabled to get updates from Windows Update or Windows Server Update Services.
Language packs
If you install a language pack after you install this update, you must reinstall this update. Therefore, we recommend that you install any language packs that you need before you install this update.
Learn about adding a language pack to Windows
Prerequisite
You must install the updates listed below and restart your device before installing the latest Monthly Rollup. Installing these updates improves the reliability of the update process and mitigates potential issues while installing the Monthly Rollup and applying Microsoft security fixes.
- The March 12, 2019 servicing stack update (SSU) (KB4490628). To get the standalone package for this SSU, search for it in the Microsoft Update Catalog. This update is required to install updates that are only SHA-2 signed.
- The latest SHA-2 update (KB4474419) released September 10, 2019. If you are using Windows Update, the latest SHA-2 update will be offered to you automatically. This update is required to install updates that are only SHA-2 signed. For more information on SHA-2 updates, see 2019 SHA-2 Code Signing Support requirement for Windows and WSUS.
- To get this security update, you must reinstall the “Extended Security Updates (ESU) Licensing Preparation Package” (KB5016892) for Windows Server 2008 R2 SP1 that is dated August 8, 2022 even if you previously installed the ESU key. The ESU licensing preparation package will be offered to you from WSUS. To get the standalone package for ESU licensing preparation package, search for it in the Microsoft Update Catalog.
- After you install the items above, we strongly recommend that you install the latest SSU.
For Windows Server 2008 R2 SP1, you must have the servicing stack update (SSU) (KB5017397) that is dated September 13, 2022 or later installed. For more information about the latest SSU updates, see ADV990001 | Latest Servicing Stack Updates.
If you use Windows Update, the latest SSU will be offered to you automatically if you are an ESU customer. To get the standalone package for the latest SSU, search for it in the Microsoft Update Catalog. For general information about SSUs, see Servicing stack updates and Servicing Stack Updates (SSU): Frequently Asked Questions.
- Download the ESU MAK add-on key from the VLSC portal and deploy and activate the ESU MAK add-on key. If you use the Volume Activation Management Tool (VAMT) to deploy and activate keys, follow the instructions here.
IMPORTANT You do not need an additional key for deployment of the following:- You do not need to deploy an additional ESU key for Azure virtual machines (VMs), Azure Stack HCI.
- For other Azure products such as Azure VMWare, Azure Nutanix solution Azure Stack (Hub, Edge), or for bring-your-own images on Azure for Windows Server 2008 SP2, and Windows Server 2008 R2 SP1 you do need to deploy the ESU key. The steps to install, activate, and deploy ESUs are the same for the fourth year of ESU coverage.
Install this update
| Release Channel | Available | Next Step |
| Windows Update and Microsoft Update | Yes | None. This update will be downloaded and installed automatically from Windows Update if you are an ESU customer. |
| Microsoft Update Catalog | Yes | To get the standalone package for this update, go to the Microsoft Update Catalog website. |
| Windows Server Update Services (WSUS) | Yes | This update will automatically sync with WSUS if you configure Products and Classifications as follows: Product: Windows Server 2008 R2 Service Pack 1, Windows Embedded Standard 7 Service Pack 1, Windows Embedded POSReady 7 Classification: Security Updates |
File information
For a list of the files that are provided in this update, download the file information for update KB5027275.
References
Learn about the standard terminology that is used to describe Microsoft software updates.
