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 IP-HTTPS Preauthentication


DirectAccess IP-HTTPS PreauthenticationRecently I’ve written about the security challenges with DirectAccess, specifically around the use of the IP-HTTPS IPv6 transition technology. In its default configuration, the DirectAccess server does not authenticate the client when an IP-HTTPS transition tunnel is established. This opens up the possibility of an unauthorized user launching Denial-of-Service (DoS) attacks and potentially performing network reconnaissance using ICMPv6. More details on this can be found here.


The best way to mitigate these security risks is to implement an Application Delivery Controller (ADC) such as the F5 BIG-IP Local Traffic Manager or the Citrix NetScaler. I’ve documented how to configure those platforms here and here.


For those organizations that do not have a capable ADC deployed, it is possible to configure the IP-HTTPS listener on the Windows Server 2012 R2 server itself to perform preauthentication.

Important Note: Making the following changes on the DirectAccess server is not formally supported. Also, this change is incompatible with one-time passwords (OTP)  and should not be performed if strong user authentication is enabled. In addition, null cipher suites will be disabled, resulting in reduced scalability and degraded performance for Windows 8.x and Windows 10 clients. Making this change should only be done if a suitable ADC is not available.

Configure IP-HTTPS Preauthentication

To configure the DirectAccess server to perform preauthentication for IP-HTTPS connections, open an elevated PowerShell command window and enter the following command.

ls Cert:\LocalMachine\My

DirectAccess IP-HTTPS Preauthentication

Copy the thumbprint that belongs to the SSL certificate assigned to the IP-HTTPS listener. Open an elevated command prompt window (not a PowerShell window!) and enter the following commands.

netsh http delete sslcert ipport=
netsh http add sslcert ipport= certhash=[thumbprint]
dsmapperusage=enable clientcertnegotiation=enable

DirectAccess IP-HTTPS Preauthentication

For load-balanced clusters and multisite deployments, repeat these steps on each DirectAccess server in the cluster and/or enterprise.


Once these changes have been made, only DirectAccess clients that have a computer certificate with a subject name that matches the name of its computer account in Active Directory will be allowed to establish an IP-HTTPS transition tunnel connection.

DirectAccess IP-HTTPS Preauthentication using F5 BIG-IP

Note: For information about configuring the Citrix NetScaler to perform IP-HTTPS preauthentication, click here. For information about configuring Windows Server 2012 R2 to perform IP-HTTPS preauthentication natively, click here.


DirectAccess IP-HTTPS Preauthentication using F5 BIG-IPRecently I wrote about security challenges with DirectAccess and the IP-HTTPS IPv6 transition technology. Specifically, IP-HTTPS transition tunnel connections are not authenticated by the DirectAccess server, only the client. This allows an unauthorized device to obtain an IPv6 address on the DirectAccess client network. With it, an attacker can perform network reconnaissance using ICMPv6 and potentially launch a variety of Denial-of-Service (DoS) attacks. For more details, click here.

Note: DirectAccess IPsec data connections not at risk. Data is never exposed at any time with the default configuration.


To mitigate these issues, it is recommended that an Application Delivery Controller (ADC) be used to terminate SSL connections and enforce client certificate authentication. Doing this will ensure that only authorized connections will be accepted by the DirectAccess server. In addition, there are some scalability and performance benefits to implementing this configuration when supporting Windows 7 clients.

Important Considerations

Performing IP-HTTPS preauthentication on the F5 BIG-IP is formally unsupported by Microsoft. In addition, terminating IP-HTTPS on the F5 appliance breaks OTP authentication.

F5 BIG-IP Configuration

To configure the F5 BIG-IP to perform SSL offload for DirectAccess IP-HTTPS, follow the guidance documented here. In addition, to configure the F5 BIG-IP to perform preauthentication for DirectAccess clients, when creating the client SSL profile, click Custom above the Client Authentication section and choose Require from the Client Certificate drop-down list and Always from the Frequency drop-down list. In addition, choose your internal PKI’s root Certification Authority (CA) certificate from the Trusted Certificate Authorities drop-down list and from the Advertised Certificate Authorities drop-down list.

DirectAccess IP-HTTPS Preauthentication using F5 BIG-IP


Enabling client certificate authentication for IP-HTTPS connections ensures that only authorized DirectAccess clients can establish a connection to the DirectAccess server and obtain an IPv6 address. It also prevents an unauthorized user from performing network reconnaissance or launching IPv6 Denial-of-Service (DoS) attacks.

DirectAccess IP-HTTPS Discovery Script for Nmap

DirectAccess IP-HTTPS Discovery Script for NmapWhen troubleshooting DirectAccess connectivity issues, the popular Nmap network mapping and discovery tool is an invaluable resource for verifying the communication path to the DirectAccess server from outside the network. However, just verifying that ports are open and listening often isn’t sufficient. In the case of IP-HTTPS, for example, the tried and true method of using telnet to verify that the port is open might be misleading. For instance, telnet might indicate that TCP port 443 is open and responding, but DirectAccess connectivity can still fail. This often happens as a result of a network configuration error that allows another network device other than the DirectAccess server to respond to HTTPS requests, which results in a false positive.

In an effort to conclusively determine that the DirectAccess server is responding, I’ve often relied on the SSL Labs Server Test site. Here I will enter the DirectAccess server’s public hostname and run the test, and from the results I can easily determine if indeed the DirectAccess server is responding by verifying that the HTTP server signature is Microsoft-HTTPAPI/2.0.

DirectAccess IP-HTTPS Discovery Script for NMAP

This usually works well, but it takes a few minutes to run the test, and there are a few scenarios in which it doesn’t work. For example, I might be working with a customer to perform some initial testing by using a local HOSTS file entry for the public name before the DNS record has been created. Also, if the SSL certificate on the DirectAccess server uses an IP address instead of a hostname (not recommended, but it is supported!) the SSL Labs server test won’t work.

Fortunately, the latest release Nmap (v7.00) now includes a script that enables the detection of Microsoft DirectAccess responding on TCP port 443. With the IP-HTTPS discovery script, it is now possible to determine not only if the port is open, but if the DirectAccess server is actually the service responding. The syntax for conducting a port scan using the IP-HTTPS discovery script for NMAP is as follows:

nmap.exe –n –Pn –p443 [directaccess_public_fqdn] –script [path_to_nmap_iphttps_discovery_script]

Here’s an example:

nmap.exe –n –Pn –p443 –script c:\tools\nmap\scripts\ip-https-discover.nse

DirectAccess IP-HTTPS Discovery Script for NMAP

Now it is possible, using just Nmap, to not only determine if the IP-HTTPS communication path is functioning, but to definitively determine that the DirectAccess server is the device responding.

Happy troubleshooting!

DirectAccess and the TLS Logjam Attack

Another critical flaw affecting Transport Layer Security (TLS) was discovered recently that could put some organizations at risk. The “Logjam” attack exploits a weakness in how the Diffie-Hellman key exchange is used. An attacker, acting as a man-in-the-middle, can potentially force a downgrade of the TLS connection, resulting in the use of weak cryptography. The Qualys SSL Labs SSL Server Test has been updated to identify this vulnerability. When testing a DirectAccess server you will receive the following warning message.

“This server supports weak Diffie-Hellman (DH) key exchange parameters. Grade capped to B.”

DirectAccess and the Logjam Attack

DirectAccess leverages SSL and TLS as part of the IP-HTTPS IPv6 transition protocol, which is used to tunnel IPv6 packets over the IPv4 Internet. These IPv6 packets are encrypted using IPsec. If an attacker were to break the SSL/TLS connection they would gain nothing. Because of this, a dedicated DirectAccess server is unaffected by the Logjam attack. Mitigating it would provide no additional protection, so you can safely ignore the warning about weak DH key exchange parameters being supported.

However, if DirectAccess has been configured to use one-time password (OTP) authentication, the client-based VPN role has been enabled and configured, or the Web Application Proxy (WAP) role has been installed on the DirectAccess server, then the Logjam attack represents a serious risk and should be mitigated. Also, in some cases it may be desirable to make this change on a dedicated DirectAccess server just to prevent an audit finding and avoid having to explain why the DirectAccess workload would be unaffected by this attack.

To mitigate this vulnerability it will be necessary to remove support for cipher suites that use the Diffie-Hellman key exchange protocol on the DirectAccess server. This is accomplished by opening the Local Group Policy Editor (gpedit.msc) on the DirectAccess server and expanding Computer Configuration, Administrative Templates, and Network. Select SSL Configuration Settings and then double-click SSL Cipher Suite Order. Select Enabled and then replace the default list of cipher suites with the following list.


DirectAccess and the Logjam Attack

Once complete, restart the DirectAccess server. The Qualys SSL Labs server test should no longer give a warning about the use of weak Diffie-Hellman keys. In addition, this reordering and optimization of cipher suites will also improve the protocol support and key exchange scores, as shown here.

DirectAccess and the Logjam Attack

As a reminder, and overall rating of “F” is expected when testing a dedicated DirectAccess server. By design, DirectAccess provides support for null cipher suites to improve scalability and performance for Windows 8.x and later DirectAccess clients. More details here.

POODLE and DirectAccess

Recently a new and very serious vulnerability in the SSL 3.0 protocol has been discovered that allows an attacker to recover sensitive information for an encrypted session. As DirectAccess uses SSL and TLS as part of the IP-HTTPS IPv6 transition protocol, I’ve had many customers ask me about mitigating this vulnerability on a DirectAccess server.

POODLE and DirectAccess

Figure 1 – Qualys SSL Labs Server Test Score for DirectAccess IP-HTTPS

However, is mitigating the POODLE attack on a DirectAccess server really necessary? Recall that, as I’ve discussed previously, the IP-HTTPS IPv6 transition protocol is only used to tunnel IPv6 traffic from the DirectAccess client to the DirectAccess server over the public IPv4 Internet. This traffic is already encrypted with IPsec, so there’s really nothing an attacker would gain by leveraging the POODLE attack on a DirectAccess session.

The recommended mitigation for the POODLE attack is to disable the use of SSL 3.0 on servers and clients. If you have deployed DirectAccess by itself, there’s no need to implement this mitigation as there is no real risk associated with this attack in this specific scenario. However, there are no negative side effects for doing so, and if you wish to disable SSL 3.0 just to avoid future audit findings, I see no problem with that.

If your DirectAccess server is also configured to support client-based VPN and you’ve enabled the Secure Sockets Tunneling Protocol (SSTP) then mitigating the POODLE attack is an excellent idea. SSTP also uses SSL and TLS, so this session could be hijacked by an attacker and sensitive information might be disclosed.

To disable SSL 3.0 on the DirectAccess server, execute the following commands from an elevated PowerShell window.

New-Item -Path "HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\SSL 3.0\Server" -Force
New-ItemProperty -Path "HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\SSL 3.0\Server" -PropertyType dword -Value 0 -Name Enabled

A restart of the server is required for the changes to take effect. To audit your DirectAccess server’s SSL and TLS configuration, visit the Qualys SSL Labs server test site. For more information about the POODLE SSL 3.0 vulnerability, click here.

DirectAccess IP-HTTPS SSL and TLS Insecure Cipher Suites

Occasionally I will get a call from a customer who has deployed DirectAccess with Windows Server 2012/R2 complaining about a security audit finding indicating that the DirectAccess server supports insecure SSL/TLS cipher suites. For example, when using the popular Tenable Nessus vulnerability scanner, a vulnerability report indicates a finding with a Medium severity level in the plug-in “SSL Null Cipher Suites Supported”. The description states that “The remote host supports the use of SSL ciphers that offer no encryption at all.”

DirectAccess IP-HTTPS SSL and TLS Insecure Cipher Suites

You can confirm this finding by using the Qualys SSL Labs SSL Server Test site. You’ll notice that the test results for a Windows Server 2012/R2 DirectAccess server indicate a score of 50 for cipher strength.

DirectAccess IP-HTTPS Insecure SSL and TLS Cipher Suites

Reviewing the details of the test results shows that the following two NULL cipher suites are indeed supported, highlighted below in red.


DirectAccess IP-HTTPS Insecure SSL and TLS Cipher Suites

Note: This doesn’t apply when the client-based VPN role is collocated with DirectAccess. More details here.

Typically this could be remedied by disabling support for NULL cipher suites using the same SSL and TLS hardening techniques described here. However, DirectAccess IP-HTTPS is unique in this scenario and the support for NULL cipher suites is by design, so employing traditional SSL and TLS security hardening techniques doesn’t apply here.

This is because DirectAccess IP-HTTPS is only used for IPv6 tunneling purposes, enabling the DirectAccess client that communicates exclusively using IPv6 to connect to the DirectAccess server over the public IPv4 Internet. IPv6 DirectAccess traffic from the client to the server is encrypted with IPsec, so the need for SSL/TLS encryption is not required, and in fact is not desirable for scalability and performance reasons. No unencrypted traffic (with the exception of ICMP) is sent over this SSL/TLS connection.

If a security audit flags support for insecure cipher suites on your Windows Server 2012/R2 DirectAccess server, you can safely ignore it.

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