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.
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.
Error code 0x80090326 translates to SEC_E_ILLEGAL_MESSAGE, indicating the client encountered a fatal error during the SSL handshake.
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.
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.
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
SSL Certificate Considerations for DirectAccess IP-HTTPS
I’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
Microsoft 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 
