Applies ToWindows Server 2008

Release Date:

10/08/2021

Version:

Security-only update

Important: Windows Server 2008 Service Pack 2 (SP2) has reached the end of mainstream support and are now in extended support. Starting in July 2020, there will no longer be optional, non-security releases (known as "C" releases) for this operating system. Operating systems in extended support have only cumulative monthly security updates (known as the "B" or Update Tuesday release). Verify that you have installed the required updates listed in the How to get this update section before installing this update.  WSUS scan cab files will continue to be available for Windows Server 2008 SP2. If you have a subset of devices running this operating system without ESU, they might show as non-compliant in your patch management and compliance toolsets.

Improvements and fixes

This security update includes quality improvements. Key changes include:

  • Changes the default privilege requirement for installing drivers when using Point and Print. After installing this update, you must have administrative privileges to install drivers. If you use Point and Print, see KB5005652, Point and Print Default Behavior Change, and CVE-2021-34481 for more information.

  • Addresses an issue in which Smart Card Authentication (PIV) fails on non-RFC compliant printers and scanners requiring smartcard authentication. For more information, see KB5005391.

  • This update also contains miscellaneous security improvements to internal OS functionality.

For more information about the resolved security vulnerabilities, please refer to the new Security Update Guide website.

Known issues in this update

Symptom

Workaround

After installing this update, the Encrypted File System (EFS) API OpenEncryptedFileRaw(A/W), often used in backup software, will not work when you back up to or from a Windows Server 2008 SP2 device. OpenEncryptedFileRaw will continue to work on all other versions of Windows (local and remote).

This behavior is expected because we addressed the issue in CVE-2021-36942.

Note If you cannot use backup software on Windows 7 SP1 and Server 2008 R2 SP1 or later after installing this update, contact the manufacturer of your backup software for updates and support.

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 are installing this update on a device that is running an edition that is not supported for ESU. For a complete list of which editions are supported, see KB4497181.

  • If you do not have an ESU MAK add-on key installed and activated.

If you have purchased 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.

Certain operations, such as rename, that you perform on files or folders that are on a Cluster Shared Volume (CSV) may fail with the error, “STATUS_BAD_IMPERSONATION_LEVEL (0xC00000A5)”. This occurs when you perform the operation on a CSV owner node from a process that doesn’t have administrator privilege.

Do one of the following:

  • Perform the operation from a process that has administrator privilege.

  • Perform the operation from a node that doesn’t have CSV ownership.

Microsoft is working on a resolution and will provide an update in an upcoming release.

How to get this update

Before installing this update

IMPORTANT Customers who have purchased the Extended Security Update (ESU) for on-premises versions of this OS must follow the procedures in KB4522133 to continue receiving security updates after extended support ends on January 14, 2020.

For more information on ESU and which editions are supported, see KB4497181.

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 Rollup and applying Microsoft security fixes.

  1. 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.

  2. 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.

  3. The Extended Security Updates (ESU) Licensing Preparation Package (KB4538484) or the Update for the Extended Security Updates (ESU) Licensing Preparation Package (KB4575904). 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 installing the items above, we strongly recommend that you install the latest SSU (KB4580971). If you are using 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.

REMINDER If you are using Security-only updates, you will also need to install all previous Security-only updates and the latest cumulative update for Internet Explorer (KB5005036).

Install this update

Release Channel

Available

Next Step

Windows Update and Microsoft Update

No

See the other options below.

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 5005095.

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