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Update Summary

KB5099536 for Windows Server 2025 (OS Build 26100.33158) includes the latest security fixes, non-security improvements from KB5094125, and a servicing stack update KB5101372. It also adds PQC TLS 1.3 support, RDP SHA-2 thumbprints, and Secure Boot certificate deployment improvements. Reference IDs: CVE-2026-56155, CVE-2025-59287.

Update Details

Security

  • Adds support for hybrid post-quantum cryptography (PQC) key exchange in TLS 1.3 to strengthen secure network connections.
  • Adds support for composite cryptographic formats that combine traditional and post-quantum algorithms in a single signature or key.
  • Introduces automatic detection of insecure DKM container ACL configurations in AD FS with an opt-in remediation mechanism for stronger permissions.
  • Enforces TDI transport registration requirements; apps using sockets over unregistered third-party TDI transports might stop working after this update.
  • Adds SHA-2 certificate thumbprint support for trusted RDP publishers and recommends migrating to SHA-256 or stronger to reduce phishing risk.
  • Includes additional high-confidence device targeting data to expand Secure Boot certificate deployment coverage.

Bug Fixes

  • Fixes third-party apps using OLE Automation with Microsoft Office that could fail to launch Office or open documents after KB5094125.
  • Improves startup performance for Hyper-V-isolated Windows Server containers.
  • Improves reliability of the Windows Event Log service on event collector servers forwarding to custom log channels.
  • Fixes File Explorer OneDrive shortcut failures when File Explorer runs in administrative mode.
  • Changes hotkey unregister and cleanup behavior for built-in Windows experiences that rely on previous hotkey lifecycle behavior.
  • Improves connections to shared network resources, including unauthenticated null session connections.
  • Fixes a Windows stop responding issue in certain situations.
  • Fixes a graphics kernel driver memory leak that affected graphics-intensive virtual machines and reduced excessive memory usage.
  • Fixes Recycle Bin confirmation dialogs showing an internal file name instead of the original file name when permanently deleting a file.

New Features

  • Adds support for hybrid post-quantum cryptography (PQC) key exchange in TLS 1.3.
  • Adds support for composite cryptographic formats combining traditional and post-quantum algorithms.
  • Adds SHA-2 certificate thumbprint support for trusted RDP publishers.
  • Introduces automatic detection of insecure DKM container ACL configurations in AD FS with opt-in remediation.

Known Issues

  • Some built-in Windows experiences that rely on previous hotkey lifecycle behavior might temporarily stop responding to certain keyboard shortcuts after the input changes.
  • Applications using sockets over unregistered third-party TDI transports might stop working after installing this update.
  • WSUS does not display synchronization error details within its error reporting after KB5070881 or later updates.

Hints

  • Updated Windows Server 2025 container base images (nanoserver, servercore, and windowsservercore) are available through Microsoft Container Registry; pull the latest image tag to get the startup performance improvement.
  • Microsoft recommends migrating RDP file security to SHA-256 thumbprints or stronger algorithms as soon as possible.
  • Secure Boot certificates are being updated through Windows Update over the coming months for supported PCs and non-managed business devices.
  • KB5101372 is the servicing stack update included with this release.
  • If you have already installed previous updates, only the new updates in this package will be downloaded and installed.

Links

Product Information

Vendor: Microsoft

Product: Windows Server 2025

Product type: Other

Application category: Utilities

Platform: Windows

Version: OS Build 26100.33158

Vendor release date: Jul 14, 2026

Published on updatealert.io: Jul 16, 2026

Description: Server operating system for next-generation on-premises and hybrid workloads.