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.

Webinar: Certificate Automation in Practice – A Technical Deep Dive

If you manage Windows Server workloads that require public TLS certificates like Always On VPN, DirectAccess, Remote Desktop Gateway, Internet Information Services (IIS), and others, you know that certificate expirations don’t send friendly reminders. Certificates expire quietly. Too often, end users are the ones who sound the alarm—when resources are already unavailable. Of course, this never happens at a convenient time. It’s usually the middle of the night, on the weekend.

Missed the event? Watch the on-demand replay here.

Current State

Most Windows IT teams are still managing certificates the same way they did years ago, using spreadsheets, calendar reminders, and an assortment of renewal scripts. It usually works… until it suddenly doesn’t.

Free Webinar

I’m pleased to announce that I’ll be joining Todd Gardner from CertKit for a free live webinar on Tuesday, June 16, at 11:00 AM CDT, in which we will break down the following:

  • Why certificate mismanagement causes so much pain at scale
  • How to build real automation that works across your full environment, including internal services and vendor appliances
  • A live demonstration of CertKit showing end-to-end discovery, monitoring, and automated renewal

There will also be time for live Q&A, so bring your questions!

Join Us!

If you’re tired of patching the problem with fragile scripts and assorted reminders, join us to learn about a fully automated solution that can dramatically improve the situation. Register now and don’t miss this opportunity to reduce your TLS certificate management burden and end the need for 2 AM certificate renewal fire drills.

Webinar Details

Webinar: TLS Certificate Automation for Windows Infrastructure
Hosts: Todd Gardner (CertKit) and Richard Hicks (Richard M. Hicks Consulting, Inc.)
Date: Tuesday, June 16
Time: 11:00 AM CDT
Registration: Click here to register!

Recording

If you are unable to attend the live session, be sure to register to receive a link to the recorded session for on-demand viewing.

Webinar: Certificate Automation for Windows Infrastructure

If you manage Windows Server workloads that require public TLS certificates like Always On VPN, DirectAccess, Remote Desktop Gateway, Internet Information Services (IIS), and others, you know that certificate expirations don’t send friendly reminders. Certificates expire quietly. Too often, end users are the ones who sound the alarm—when resources are already unavailable. Of course, this never happens at a convenient time. It’s usually the middle of the night, on the weekend.

Did you miss the webinar? You can view it on demand here!

Current State

Most Windows IT teams are still managing certificates the same way they did years ago, using spreadsheets, calendar reminders, and an assortment of renewal scripts. It usually works… until it suddenly doesn’t.

Free Webinar

I’m pleased to announce that I’ll be joining Todd Gardner from CertKit for a free live webinar on Tuesday, May 26, at 11:00 AM CDT, in which we will break down the following:

  • Why certificate mismanagement causes so much pain at scale
  • How to build real automation that works across your full environment, including internal services and vendor appliances
  • A live demonstration of CertKit showing end-to-end discovery, monitoring, and automated renewal

There will also be time for live Q&A, so bring your questions!

Join Us!

If you’re tired of patching the problem with fragile scripts and assorted reminders, join us to learn about a fully automated solution that can dramatically improve the situation. Register now and don’t miss this opportunity to reduce your TLS certificate management burden and end the need for 2 AM certificate renewal fire drills.

Webinar Details

Webinar: TLS Certificate Automation for Windows Infrastructure
Hosts: Todd Gardner (CertKit) and Richard Hicks (Richard M. Hicks Consulting, Inc.)
Date: Tuesday, May 26
Time: 11:00 AM CDT
Registration: Click here to register!

Recording

If you missed the live event, you can view the on demand recording here!