Patch Review Recommendations

Flexis May 2026 Patch Recommendation

Patches Microsoft released in May 2026

 

  • KB5087545: – 2026-05 Cumulative Update for Microsoft server operating system version 21H2 for x64-based Systems
  • KB5087538: – 2026-05 Cumulative Update for Windows Server 2019 for x64-based Systems
  • KB50880642026-05 Servicing Stack Update for Windows Server 2016 for x64-based Systems.
  • KB50875372026-05 Cumulative Update for Windows Server 2016 for x64-based Systems 

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Microsoft Windows

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Microsoft Edge

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Microsoft Edge

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Internet Explorer

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Microsoft Office and Microsoft Office Services and Web Apps

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Windows Defender

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Visual Studio

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Chakra Core

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Microsoft Dynamics

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.NET Framework

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.NET Core

Please note the following information regarding the security updates:

Windows 10 Enterprise and Education and Windows 10 Home and Pro Lifecycle pages, Windows 10 was ended on October 14, 2025. The current version, 22H2, will be the final version of Windows 10. The following editions will remain in support with monthly security update releases through that date: 

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Pro

Pro Education

Pro for Workstations

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Enterprise multi-session

KB5087545: Windows Server 2022

Improvements 

This security update contains fixes and quality improvements from KB5082142 ​​​​​​​(released April 14, 2026) and KB5091575 (released April 19, 2026). The following summary outlines key issues addressed by this update. Also, included are available new features. The bold text within the brackets indicates the item or area of the change. 

  • [Secure Boot] 
  • With this update, Windows quality updates include additional high confidence device targeting data, increasing coverage of devices eligible to automatically receive new Secure Boot certificates. Devices receive the new certificates only after demonstrating sufficient successful update signals, maintaining a controlled and phased rollout.​​​​​​​ 
  • This update adds a new SecureBoot folder under C:\Windows on eligible devices. The folder contains example scripts intended for organizations with IT professionals who actively manage updates across their device fleet. These scripts can be used to detect Secure Boot certificate update status and automate deployment via a safe rollout mechanism in an Active Directory environment. For more information, see Sample Secure Boot E2E Automation Guide. 
  • [App] This update improves the accuracy and reliability of calculations used by apps and system components. Users and developers should see more consistent results, especially when working with very small values. 
  • [Daylight saving time (DST)] This update supports the 2023 DST change for the Arab Republic of Egypt. 
  • [Desktop] This update improves how the Windows Server interface responds during everyday use. Users should notice smoother interactions and fewer instances where windows stop responding. 
  • [Sign-In] After you install the Windows update released on or after March 10, 2026, some users might experience an issue signing in to apps with a Microsoft account. Even when the device has a working Internet connection, a “no Internet” error appears during sign in and prevents access to Microsoft services and apps such as Microsoft Teams. 
  • [Remote Desktop (known issue)] Fixed: This update addresses an issue that affects the Remote Desktop Connection security warning dialog. The dialog could render incorrectly in multi-monitor scenario when the monitors had different scaling set. This might occur after installing the April 2026 (KB5082142) security update. For more information, see Understanding security warnings when opening Remote Desktop (RDP) files. 

 

 

Known issues in this update 

Devices with an unrecommended BitLocker Group Policy configuration might be required to enter their BitLocker recovery Key 

Symptom 

Some devices with an unrecommended BitLocker Group Policy configuration might be required to enter their BitLocker recovery key on the first restart after installing this update. 

This issue only affects a limited number of systems in which ALL of the following conditions are true. These conditions are unlikely to be found on personal devices not managed by IT departments. 

  1. BitLocker is enabled on the OS drive. 
  2. The Group Policy “Configure TPM platform validation profile for native UEFI firmware configurations” is configured, and PCR7 is included in the validation profile (or the equivalent registry key is set manually). 
  3. System Information (msinfo32.exe) reports Secure Boot State PCR7 Binding as “Not Possible”. 
  4. The Windows UEFI CA 2023 certificate is present in the device’s Secure Boot Signature Database (DB), making the device eligible for the 2023signed Windows Boot Manager to be made the default. 
  5. The device is not already running the 2023-signed Windows Boot Manager. 

In this scenario, the BitLocker recovery key only needs to be entered once — subsequent restarts will not trigger a BitLocker recovery screen, as long as the group policy configuration remains unchanged. For help finding your BitLocker recovery key, see the article, Find your BitLocker recovery key. 

Enterprises are recommended to audit their BitLocker group policies for explicit PCR7 inclusion and check msinfo32.exe for their PCR7 binding status before installing this update. (See the Workaround below.) 

Workaround  

Remove the Group Policy configuration before installing the update (Recommended)  

  1. Open Group Policy Editor (gpedit.msc) or your Group Policy Management Console. 
  2. Navigate to: Computer Configuration > Administrative Templates > Windows Components > BitLocker Drive Encryption > Operating System Drives. 
  3. Set “Configure TPM platform validation profile for native UEFI firmware configurations” to “Not Configured”. 
  4. Run the following command on affected devices to propagate the policy change: gpupdate /force 
  5. Run the following command to suspend BitLocker (where BitLocker is enabled on the C: drive): manage-bde -protectors -disable C: 
  6. Run the following command to resume BitLocker (where BitLocker is enabled on the C: drive): manage-bde -protectors -enable C: 
  7. ​​​​These updates the BitLocker bindings to use the Windows-selected default PCR profile. 

A permanent resolution for this issue is planned in a future Windows update. More information will be provided when it is available. 

 

Windows Server Update Services (WSUS) does not display error details 

After installing KB5070884 or later updates, Windows Server Update Services (WSUS) does not display synchronization error details within its error reporting. This functionality is temporarily removed to address the Remote Code Execution Vulnerability, CVE-2025-59287.

KB5087538: Windows Server 2019 Win 10 Ent LTSC 2019

Windows Secure Boot certificate expiration 

Important: Secure Boot certificates used by most Windows devices are set to expire starting in June 2026. This might affect the ability of certain personal and business devices to boot securely if not updated in time. To avoid disruption, we recommend reviewing the guidance and taking action to update certificates in advance.   

 

Summary 

Windows Server 2019 

Applies to: Windows Server 2019 

This security update includes fixes and quality improvements that are part of the following update: 

The following is a summary of the issues that this update addresses when you install this update. The bold text within the brackets indicates the item or area of the change we are documenting. 

  • [Remote Desktop security warnings (known issue)] Fixed: The Remote Desktop Connection security warning dialog might render incorrectly in multi-monitor configurations with different display scaling settings. This issue might occur after installing the Windows security update released on or after April 14, 2026 (such as KB5082123). 
  • [Secure Boot] 
  • This update enables dynamic status reporting for Secure Boot states in Windows Security App. 
  • With this update, Windows quality updates include additional high confidence device targeting data, increasing coverage of devices eligible to automatically receive new Secure Boot certificates. Devices receive the new certificates only after demonstrating sufficient successful update signals, maintaining a controlled and phased rollout. 
  • This update adds a new SecureBoot folder under C:\Windows on eligible devices. The folder contains example scripts intended for organizations with IT professionals who actively manage updates across their device fleet. These scripts can be used to detect Secure Boot certificate update status and automate deployment via a safe rollout mechanism in an Active Directory environment. For more information, see Sample Secure Boot E2E Automation Guide. 
  • [Sign-In] Fixed: After you install the Windows update released on or after March 10, 2026, some users might experience an issue signing in to apps with a Microsoft account. Even when the device has a working Internet connection, a “no Internet” error appears during sign in and prevents access to Microsoft services and apps such as Microsoft Teams. 
  • [Daylight Savings Time] Update for Arab Republic of Egypt to support the government DST change order in 2023. 

 

 

Applies to: Windows 10 Enterprise LTSC 2019 

This security update includes fixes and quality improvements that are part of the following update: 

The following is a summary of the issues that this update addresses when you install this update. The bold text within the brackets indicates the item or area of the change we are documenting. 

  • [Remote Desktop security warnings (known issue)] Fixed: The Remote Desktop Connection security warning dialog might render incorrectly in multi-monitor configurations with different display scaling settings. This issue might occur after installing the Windows security update released on or after April 14, 2026 (such as KB5082123). 
  • [Secure Boot] 
  • This update enables dynamic status reporting for Secure Boot states in Windows Security App. 
  • With this update, Windows quality updates include additional high confidence device targeting data, increasing coverage of devices eligible to automatically receive new Secure Boot certificates. Devices receive the new certificates only after demonstrating sufficient successful update signals, maintaining a controlled and phased rollout. 
  • This update adds a new SecureBoot folder under C:\Windows on eligible devices. The folder contains example scripts intended for organizations with IT professionals who actively manage updates across their device fleet. These scripts can be used to detect Secure Boot certificate update status and automate deployment via a safe rollout mechanism in an Active Directory environment. For more information, see Sample Secure Boot E2E Automation Guide. 
  • [Sign-In] Fixed: After you install the Windows update released on or after March 10, 2026, some users might experience an issue signing in to apps with a Microsoft account. Even when the device has a working Internet connection, a “no Internet” error appears during sign in and prevents access to Microsoft services and apps such as Microsoft Teams. 
  • [Daylight Savings Time] Update for Arab Republic of Egypt to support the government DST change order in 2023. 

KB5088064: Win 10 Ent LTSB 2016 Win 10 IoT Ent LTSB 2016 Windows Server 2016, all editions

Windows Secure Boot certificate expiration  

Important: Secure Boot certificates used by most Windows devices are set to expire starting in June 2026. This might affect the ability of certain personal and business devices to boot securely if not updated in time. To avoid disruption, we recommend reviewing the guidance and taking action to update certificates in advance.   

 

Summary 

This servicing stack update (SSU) makes quality improvements to the servicing stack, which is the component that installs Windows updates. Servicing stack updates make sure that you have a robust and reliable servicing stack so that your devices can receive and install Microsoft updates. 

Important Not installing the latest SSU before applying Windows updates might result in the Windows update not being offered until the latest SSU is installed. 

KB5087537:- Windows Server 2016, all editions Win 10 Ent LTSB 2016 Win 10 IoT Ent LTSB 2016

Windows Secure Boot certificate expiration 

Important: Secure Boot certificates used by most Windows devices are set to expire starting in June 2026. This might affect the ability of certain personal and business devices to boot securely if not updated in time. To avoid disruption, we recommend reviewing the guidance and taking action to update certificates in advance.   

 

 

Summary 

Windows Server 2016 

Applies to: Windows Server 2016 

This security update includes fixes and improvements that are a part of the following update: 

The following is a summary of the issues that this update addresses. The bold text within the brackets indicates the item or area of the change we are documenting. 

  • [Remote Desktop security warnings (known issue)] Fixed: The Remote Desktop Connection security warning dialog might render incorrectly in multi-monitor configurations with different display scaling settings. This issue might occur after installing the Windows security update released on or after April 14, 2026 (such as KB5082198). 
  • [Sign-In] Fixed: After you install the Windows update released on or after March 10, 2026, some users might experience an issue signing in to apps with a Microsoft account. Even when the device has a working Internet connection, a “no Internet” error appears during sign in and prevents access to Microsoft services and apps such as Microsoft Teams. 
  • [Daylight Savings Time (DST)] Update for Arab Republic of Egypt to support the government DST change order in 2023. 
  • [Secure Boot] 
  • With this update, Windows quality updates include additional high confidence device targeting data, increasing coverage of devices eligible to automatically receive new Secure Boot certificates. Devices receive the new certificates only after demonstrating sufficient successful update signals, maintaining a controlled and phased rollout. ​​​​​​ 
  • This update adds a new SecureBoot folder under C:\Windows on eligible devices. The folder contains example scripts intended for organizations with IT professionals who actively manage updates across their device fleet. These scripts can be used to detect Secure Boot certificate update status and automate deployment via a safe rollout mechanism in an Active Directory environment. For more information, see Sample Secure Boot E2E Automation Guide. 
  •  

Windows 10 Version 1607 

Applies to: Windows 10 Enterprise LTSB 2016 and Windows 10 IoT Enterprise 2016 LTSB 

This security update includes fixes and improvements that are a part of the following update: 

The following is a summary of the issues that this update addresses. The bold text within the brackets indicates the item or area of the change we are documenting. 

  • [Remote Desktop security warnings (known issue)] Fixed: The Remote Desktop Connection security warning dialog might render incorrectly in multi-monitor configurations with different display scaling settings. This issue might occur after installing the Windows security update released on or after April 14, 2026 (such as KB5082198). 
  • [Sign-In] Fixed: After you install the Windows update released on or after March 10, 2026, some users might experience an issue signing in to apps with a Microsoft account. Even when the device has a working Internet connection, a “no Internet” error appears during sign in and prevents access to Microsoft services and apps such as Microsoft Teams. 
  • [Daylight Savings Time (DST)] Update for Arab Republic of Egypt to support the government DST change order in 2023. 
  • [Secure Boot] This update adds a new SecureBoot folder under C:\Windows on eligible devices. The folder contains example scripts intended for organizations with IT professionals who actively manage updates across their device fleet. These scripts can be used to detect Secure Boot certificate update status and automate deployment via a safe rollout mechanism in an Active Directory environment. For more information, see Sample Secure Boot E2E Automation Guide. 

If you installed earlier updates, only the new updates contained in this package will be downloaded.