August 10, 2021—KB5005090 (Monthly Rollup)

**Important:**Windows Server 2008 Service Pack 2 (SP2) has reached the end of mainstream support and is 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 theHow 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, see the Windows Server 2008 Service Pack 2 update history home page.

Improvements and fixes

This security update includes improvements and fixes that were a part of update KB5004305 (released July 13, 2021) and addresses the following issues:

• 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 KB5005390.
• 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

• 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 these operating systems must follow the procedures in KB4522133 to continue receiving security updates after extended support ends on January 14, 2020.For more information about ESU and which editions are supported, see KB4497181.Prerequisite:You must install the updates listed below andrestart 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, Microsoft strongly recommends 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.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 2Classification: Security Updates

File information

For a list of the files that are provided in this update, download the file information for update 5005090.