Troubleshooting DirectAccess IP-HTTPS Error 0x80090326

A Windows 7 or Windows 8.x/10 client may fail to establish a DirectAccess connection using the IP-HTTPS IPv6 transition technology. When troubleshooting this issue, running ipconfig.exe shows that the media state for the tunnel adapter iphttpsinterface is Media disconnected.

Troubleshooting DirectAccess IP-HTTPS Error 0x80090326

Running the Get-NetIPHttpsState PowerShell command on Windows 8.x/10 clients or the netsh interface httpstunnel show interface command on Windows 7 clients returns and error code of 0x80090326, with an interface status Failed to connect to the IPHTTPS server; waiting to reconnect.

Troubleshooting DirectAccess IP-HTTPS Error 0x80090326

Error code 0x80090326 translates to SEC_E_ILLEGAL_MESSAGE, indicating the client encountered a fatal error during the SSL handshake.

Troubleshooting DirectAccess IP-HTTPS Error 0x80090326

There are a number of things that can cause this to happen. The most common scenario occurs when an Application Delivery Controller (ADC) is improperly configured to perform client certificate authentication for IP-HTTPS connections. Common examples are an incorrect or missing root CA certificate, or null SSL/TLS cipher suites not enabled when supporting Windows 8.x/10 clients.

To troubleshoot DirectAccess IP-HTTPS error 0x80090326, perform a network trace on the DirectAccess client and observe the TLS handshake for clues as to which configuration error is the culprit. If the TLS handshake failure occurs immediately after the client sends a Client Hello, it is likely that the ADC does not have null cipher suites enabled.

Troubleshooting DirectAccess IP-HTTPS Error 0x80090326

If the TLS handshake failure occurs after the Server Hello, it is likely that the ADC is configured to perform client certificate authentication incorrectly, or the client does not have a valid certificate.

Troubleshooting DirectAccess IP-HTTPS Error 0x80090326

IP-HTTPS error 0x80090326 can also occur if an intermediary device is performing SSL/TLS inspection or otherwise tampering with the TLS request. It can also happen if the edge firewall and/or NAT device is forwarding IP-HTTPS connections to the wrong internal server, or if the firewall itself is responding to the HTTPS connection request. Remember, just because the server is responding on TCP port 443 doesn’t necessarily mean that it is the DirectAccess server responding!

Additional Information

Troubleshooting DirectAccess IP-HTTPS Error Code 0x90320

Troubleshooting DirectAccess IP-HTTPS Error 0x2af9

DirectAccess Troubleshooting Consulting Services

Implementing DirectAccess with Windows Server 2016

DirectAccess Troubleshooting and Configuration Training at TechMentor Redmond 2017

DirectAccess and Windows 10 in EducationI’m really excited to announce that I have once again been invited to speak at the upcoming TechMentor event in Redmond, WA August 7-11, 2017! This year I’ll be presenting two important deep-dive training sessions on DirectAccess. The first is a three-hour course on implementing DirectAccess using Windows Server 2016. This session will cover infrastructure prerequisites as well as tips, tricks, and best practices for implementing DirectAccess using Windows Server 2016. In addition I will also be delivering a three-hour deep dive on DirectAccess troubleshooting. In this session, I’ll share valuable insight, tools, and techniques for quickly identifying and resolving many common DirectAccess connectivity and performance issues. In addition I will also be giving a short talk on getting started with Azure site-to-site networking. If you want to take advantage of the power and flexibility that the Azure public cloud has to offer, extending your on-premises datacenter using site-to-site VPN is essential.

Register today using code TMSPK05 and save!

M01: Implementing DirectAccess with Windows Server 2016
T03: DirectAccess Troubleshooting Deep Dive
T07: Getting Started with Azure Site-to-Site Networking

TechMentor Redmond 2017

DirectAccess No Longer Supported in Microsoft Azure

DirectAccess No Longer Supported on Windows Server in AzureMicrosoft has historically not supported DirectAccess running on Windows Server in the Microsoft Azure public cloud. In the past, this was due to limitations imposed by the underlying cloud infrastructure, as I documented here. When Microsoft moved from the old service manager model (classic) to the newer resource manager infrastructure, many of the issues that prevented the DirectAccess workload from being stable were resolved. There are still some fundamental limitations to deploying DirectAccess in Azure as I documented here, but for the most part it was a workable solution. In fact, Microsoft even updated their support statement for DirectAccess on Azure, quietly removing it from the unsupported roles list in July 2016.

Sadly, Microsoft has reversed their decision on the support of DirectAccess in Azure. As many of you have noticed or commented on some of my posts, Microsoft recently added clarification on support for remote access on Windows Server in Azure, explicitly indicating that DirectAccess was not included in Remote Access support.


You’ll be glad to know that DirectAccess is indeed supported in Amazon’s public cloud infrastructure, Amazon Web Services (AWS). I’ll be drafting some guidance for deploying DirectAccess in AWS soon. Stay tuned!

Additional Resources

Azure Resource Manager vs. Classic Deployment: Understand Deployment Models and the State of your Resources

Deploying DirectAccess in Microsoft Azure

Implementing DirectAccess in Windows Server 2016 Book

Implementing DirectAccess with Windows Server 2016 Pre-Order

Update: My new DirectAccess book is now available for purchase. Details here.

I am pleased to announce that my new book, Implementing DirectAccess with Windows Server 2016 from Apress Media, is now available for pre-order on!

Implementing DirectAccess with Windows Server 2016

This book contains detailed and prescriptive guidance for the planning, design, implementation, and support of a DirectAccess remote access solution on Windows Server 2016. It also includes valuable insight, tips, tricks, and best practice recommendations gained from my many years of deploying DirectAccess for some of the largest organizations in the world.

Current DirectAccess administrators will also find this book helpful, as the majority of content is still applicable to DirectAccess in Windows Server 2012 and Windows Server 2012 R2. In addition, the book also includes essential information on the design and deployment of highly available and geographically redundant DirectAccess deployments.

Troubleshooting DirectAccess can be a daunting task, so I’ve dedicated an entire chapter in the book to this topic. For those responsible for the maintenance and support of DirectAccess in their organization, this chapter alone will be worth the investment.

Be sure to reserve your copy today!

3 Important Things You Need to Know about Windows 10 and DirectAccess

DirectAccess and Windows 10 - Better TogetherDirectAccess has been with us for quite some time know, having been originally introduced with Windows Server 2008 R2, later enhanced with Forefront Unified Access Gateway (UAG) 2010, and finally integrated in to the base operating system in Windows Server 2012 R2. Client support for DirectAccess begins with Windows 7 (Enterprise or Ultimate), and also includes Windows 8.x (Enterprise) and Windows 10 (Enterprise or Education).

Although Windows 7 clients are supported for DirectAccess, Windows 10 is highly preferred. Here are three important things you need to know about using Windows 10 with DirectAccess.

  1. Windows 10 Provides Improved Performance and Scalability – Windows 10 includes support for null encryption when using the IP-HTTPS IPv6 transition protocol. This eliminates the needless double-encryption performed by Windows 7 clients, and dramatically reduces the protocol overhead for clients connecting behind port-restricted firewalls. DirectAccess servers can support many more concurrent IP-HTTPS sessions with Windows 10, and it has the added benefit of making the more secure perimeter/DMZ deployment behind an edge security device performing NAT much more attractive.
  2. Windows 10 Supports Geographic Redundancy – Windows 10 includes full support for DirectAccess multisite deployments. Where Windows 7 clients had to be assigned to a single entry point, Windows 10 clients are aware of all entry points in the organization. They are able to automatically select the nearest entry point on startup, and transparently failover to another site if the current site becomes unavailable.
  3. Windows 10 Features an Enhanced Management Experience – From a troubleshooting and support perspective, Windows 10 makes things much easier. The DirectAccess connectivity assistant, an optional component for Windows 7, is now fully integrated with the Windows 10 UI. PowerShell is greatly improved and now includes many native DirectAccess configuration and troubleshooting commands.

As you can see, there are a number of significant advantages for using Windows 10 with DirectAccess. Windows 10 now supports all of the enterprise features of DirectAccess, including geographic redundancy and performance and scalability improvements. Windows 10 is also easier to troubleshoot and manage. If you’re still supporting Windows 7, DirectAccess in Windows Server 2012 R2 can certainly support them. However, without a doubt the best experience, both from an administrator’s and the end user’s perspective, is with Windows 10. Just one more reason to begin planning your migration to Windows 10 with DirectAccess today!

Need assistance with implementing  DirectAccess with Windows 10? I can help! More details here.

DirectAccess Client and Server Settings GPOs Deleted

Microsoft Windows Server Active DirectoryFor DirectAccess deployments where domain controllers are running Windows Server 2003 or Windows Server 2003 R2 using the File Replication Service (FRS) for replication, DirectAccess client and server settings Group Policy Objects (GPOs) may be deleted. If these GPOs are deleted, DirectAccess connectivity will be disrupted. If the GPOs cannot be recovered via backup, it will be necessary to rebuild the entire DirectAccess deployment from scratch.

Microsoft recently updated their DirectAccess Unsupported Configurations documentation to reflect new guidance for DirectAccess deployments where the FRS is used for the distribution of Active Directory GPOs. DirectAccess is no longer supported in environments where FRS is used for SYSVOL replication.

What this means is that if you plan to deploy DirectAccess, domain controllers must be running Windows Server 2008 or later, and Distributed File System Replication (DFS-R) must be used for replication.

More details can be found here.

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