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Always On VPN Security Updates July 2026

Microsoft released the July 2026 Windows security updates today, including several fixes that directly affect Always On VPN deployments. This month’s release addresses vulnerabilities in the Secure Socket Tunneling Protocol (SSTP), Internet Key Exchange (IKE), and the Routing and Remote Access Service (RRAS), making it an important update for organizations using Always On VPN.

SSTP Remote Code Execution

The highest-priority issue for Always On VPN administrators is a Remote Code Execution (RCE) vulnerability affecting the Secure Socket Tunneling Protocol (SSTP). SSTP is commonly used for Always On VPN user tunnel connections. Because SSTP is, by design, exposed directly to the Internet, vulnerabilities affecting this protocol deserve immediate attention. Microsoft rates this vulnerability as Critical with a CVSS base score of 8.1.

CVE-2026-50694 – Windows SSTP Remote Code Execution Vulnerability

IKE Vulnerabilities

These vulnerabilities primarily affect IKE-based VPN connections and could allow an attacker to disrupt VPN connectivity using specially crafted packets. While Microsoft rates these vulnerabilities as Important rather than Critical, organizations should still plan to deploy these updates promptly.

CVE-2026-50721 – IKEv1 Denial of Service via RSA-SHA1 authentication payload

CVE-2026-50722 – IKEv2 Denial of Service via RSA-SHA1 authentication payload

CVE-2026-12413 – IKEv2 Denial of Service via malformed fragmentation

CVE-2026-50696 – IKE Protocol Denial of Service Vulnerability

RRAS Vulnerabilities

The July 2026 security updates also address several vulnerabilities in the Windows Server Routing and Remote Access Service (RRAS). All are rated Important by Microsoft.

CVE-2026-57096 – Windows RRAS Elevation of Privilege Vulnerability

CVE-2026-49791 – Windows RRAS Elevation of Privilege Vulnerability

CVE-2026-50451 – Windows RRAS Elevation of Privilege Vulnerability

Summary

The SSTP RCE vulnerability is particularly concerning because the service is typically exposed to the Internet and could allow an unauthenticated attacker to execute code remotely. Organizations should prioritize deployment of this update. The IKE and RRAS vulnerabilities are rated Important and can generally be addressed during the next scheduled maintenance window, although administrators should avoid unnecessary delays in applying these updates.

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by Richard M. Hicks on July 14, 2026  •  Permalink
Posted in Always On VPN, AOVPN, Enterprise, enterprise mobility, Hotfix, IKEv2, Infrastructure, Microsoft, Operational Support, Patch Tuesday, RCE, Remote Access, routing and remote access service, RRAS, Secure Socket Tunneling Protocol, Security, Security Update, SSTP, Update, VPN, Vulnerability, Windows 10, Windows 11, Windows Server 2016, Windows Server 2019, Windows Server 2022, Windows Server 2025
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Posted by Richard M. Hicks on July 14, 2026

https://directaccess.richardhicks.com/2026/07/14/always-on-vpn-security-updates-july-2026/

Windows Server 2025 Marks the End of Microsoft DirectAccess

Well, the time has finally come. Microsoft DirectAccess, first introduced in Windows Server 2008 R2, will be removed from the next release of Windows Server. This means that Windows Server 2025 is officially the end of the line for DirectAccess.

Why Is This Happening?

DirectAccess has had a good run, no doubt. However, DirectAccess is built on legacy technologies, making it difficult to implement and support in modern environments. For example, DirectAccess requires the following:

  • Domain-joined servers and clients
  • Active Directory group policy management
  • NTLMv2 for authentication
  • Complex IPv6 transition and translation technologies

Further, DirectAccess does not support:

  • Modern endpoint management using Microsoft Intune
  • Integration with Entra ID and Entra Conditional Access
  • Fine-grained user access control (zero trust)
  • Windows Professional or other non-Microsoft endpoints

Microsoft’s strategic focus has shifted toward cloud-native identity, device management, and Zero Trust access solutions, making DirectAccess increasingly difficult to align with modern enterprise requirements and ultimately resulting in Microsoft discontinuing DirectAccess.

What’s Next

Organizations should consider migrating from DirectAccess to Always On VPN or Entra Private Access. Always On VPN provides a traditional VPN-based remote access solution with broad deployment flexibility, while Entra Private Access offers a cloud-native Zero Trust approach for accessing private applications and resources.

Migration Path

Organizations currently relying on DirectAccess should begin planning their migration strategy now. Although Windows Server 2025 continues to support DirectAccess, future Windows Server releases will not, making proactive migration planning essential.

Get Expert Guidance on DirectAccess Migration

Every DirectAccess deployment is different. The right migration strategy depends on your existing infrastructure, identity platform, management approach, and security requirements. Complete the form below to discuss your environment and receive guidance on transitioning to Always On VPN or Entra Private Access.

Additional Information

Microsoft DirectAccess Deprecation on Future Windows Server Releases

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by Richard M. Hicks on June 12, 2026  •  Permalink
Posted in Deployment, DirectAccess, DirectAccess Deprecated, DirectAccess End of Life, DirectAccess EOL, end of life, Enterprise, enterprise mobility, Infrastructure, Microsoft, Operational Support, Remote Access, Security, Windows 10, Windows 11, Windows 7, Windows 8, Windows 8.1, Windows Server 2008 R2, Windows Server 2012, Windows Server 2012 R2, Windows Server 2016, Windows Server 2019, Windows Server 2022, Windows Server 2025
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Posted by Richard M. Hicks on June 12, 2026

https://directaccess.richardhicks.com/2026/06/12/windows-server-2025-marks-the-end-of-microsoft-directaccess/

Mastering Certificates with Microsoft Intune September 2026

I’m excited to announce that I will be delivering another edition of the Mastering Certificates with Microsoft Intune course, hosted by ViaMonstra Online Academy. This is a three-day live online training course that takes place September 1-3, 2026. This course dives deep into issuing and managing certificates using Microsoft Intune, covering both on-premises and cloud-based solutions.

Course Overview

This interactive training equips IT professionals with the skills to provision and manage enterprise PKI certificates using Microsoft Intune. It explores Active Directory Certificate Services (AD CS), Microsoft Cloud PKI for Intune, and non-Microsoft solutions, with live demonstrations featuring real-world scenarios.

Key Learning Objectives

Those taking the online training course will learn the following.

  • Certificate Basics: Understand certificate roles and enterprise use cases.
  • Deployment Options: Master Intune certificate deployment (Intune policies, revocation, security) and Microsoft Cloud PKI (licensing, benefits, limitations, BYOCA).
  • Intune Deployment: Learn PKCS and SCEP deployment, security best practices, and troubleshooting.
  • High Availability: Explore strategies for reliable certificate management.

Course Highlights

Here are some key highlights for attendees of the training.

  • Expert-Led: Learn from a veteran IT professional, a Microsoft MVP, with deep PKI and Intune expertise.
  • Interactive Demonstrations: The course includes numerous practical exercises in real-world scenarios.
  • Resources: Access to security best practices and sample scripts for automated configuration.
  • Community: Join a private Facebook group for peer collaboration.
  • Live Q&A: Engage directly with the instructor for a clearer understanding.

Who Should Attend?

This training event is ideal for IT administrators, security professionals, and systems engineers working with Intune, AD CS, or Microsoft Cloud PKI for Intune.

Prerequisites

Those attending the online training course should be familiar with the following.

  • Basic networking knowledge (TCP/IP, DNS).
  • Familiarity with Active Directory, Windows OS, and Intune.
  • Access to an AD CS setup and an Azure subscription with Intune Suite licenses.

Why It Matters

Certificates are vital for secure authentication and communication. This course bridges theory and practice, equipping you to deploy and manage digital certificates effectively in cloud-native environments.

Details

Here is some additional information about the training event.

  • When: September 1-3, 2026 (sessions begin at 9:00 AM CDT).
  • Where: Live online via ViaMonstra Online Academy.
  • Cost: $2,395.00 (Sold separately – not included in All-Access Pass).

Why ViaMonstra?

ViaMonstra delivers top-tier IT training from Microsoft MVPs, focusing on practical, up-to-date skills and fostering a collaborative community.

Take the Next Step

Ready to master certificate management with Microsoft Intune? Register at ViaMonstra Online Academy for the August 2025 Mastering Certificates with Microsoft Intune training course today!

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by Richard M. Hicks on June 8, 2026  •  Permalink
Posted in Active Directory, Active Directory Certificate Services, AD CS, administration, authentication, Azure Active Directory, Azure AD, CBA, Certificate Authentication, Certificate Authority, Certificate Connector for Intune, Certificate Services, Certificate-Based Authentication, certificates, cloud, Cloud PKI, Cloud Service, Cryptography, Deployment, Device Management, education, Encryption, Endpoint Manager, Enterprise, enterprise mobility, Entra, Entra CBA, Entra Certificate-Based Authentication, Entra ID, Infrastructure, Intune, Intune Certificate Connector, Intune PFX Connector, learning, MDM, MEM, Microsoft, Microsoft Endpoint Manager, Microsoft Entra, Microsoft Entra ID, Microsoft Intune, Mobile Device Management, Mobility, NDES, Network Device Enrollment Service, Network Device Enrollment Services, Operational Support, PFX Connector, PKCS, PKI, public cloud, public key infrastructure, SCEP, Security, Simple Certificate Enrollment Protocol, systems management, Training, troubleshooting, Trusted Platform Module, Windows 10, Windows 11, Windows Server 2016, Windows Server 2019, Windows Server 2022, Windows Server 2025
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Posted by Richard M. Hicks on June 8, 2026

https://directaccess.richardhicks.com/2026/06/08/mastering-certificates-with-microsoft-intune-september-2026/

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