October 10, 2023—KB5031416 (Monthly Rollup)
Applies To
Windows Server 2008 Datacenter ESU Windows Server 2008 Standard ESU Windows Server 2008 Enterprise ESURelease Date:
10/10/2023
Version:
Monthly Rollup
REMINDER
Windows Server 2008 SP2 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 SP2 workloads with free Extended Security Updates.
For customers who need additional time to upgrade and modernize their devices running Windows Server 2008 SP2 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.
We recommend that you upgrade to a later version of Windows Server.
Summary
Learn more about this cumulative security update, including improvements, any known issues, and how to get the update.
NOTE 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.
For information about the various types of Windows updates, such as critical, security, driver, service packs, and so on, please see the following article. To view other notes and messages for Windows Server 2008 SP2, see the following update history home page.
Improvements
This cumulative security update contains improvements that are part of update KB5030271 (released September 12, 2023). This update also makes improvements for the following issues:
-
Addresses an issue in which an external bind might fail after Windows updates released on or after May 2023 are installed. This leads to issues with Lightweight Directory Access Protocol (LDAP) queries and authentication.
-
This update includes daylight saving time (DST) changes for Greenland. For more information, see the Daylight Saving Time & Time Zone Blog.
For more information about the resolved security vulnerabilities, please refer to the Deployments | Security Update Guide and the October 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 this operating system must follow the procedures in KB4522133 to continue receiving security updates.
For more information about ESU and which editions are supported, see KB4497181.
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 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 April 9, 2019 servicing stack update (SSU) (KB4493730). 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.
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The latest SHA-2 update (KB4474419) released October 8, 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 "Update for the Extended Security Updates (ESU) Licensing Preparation Package" (KB5016891) for Windows Server 2008 SP2 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 SP2, you must have the servicing stack update (SSU) (KB5031659) or a later SSU 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, version 21H2 and later.
-
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, 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.
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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 Service Pack 2 Classification: Security Updates |
File information
For a list of the files that are provided in this update, download the file information for update KB5031416.
References
Learn about the standard terminology that is used to describe Microsoft software updates.
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