DirectAccess IP-HTTPS and Symantec SSL Certificates

DirectAccess IP-HTTPS and Symantec SSL CertificatesAn SSL certificate is required to support the IP-HTTPS IPv6 transition technology when configuring DirectAccess. Implementation best practices dictate using a public SSL certificate signed by a trusted third-party vendor such as Entrust, Verisign, DigiCert, and others. SSL certificates issued by a private PKI are acceptable if the client trusts the issuing CA. Self-signed certificates are supported in some deployment scenarios, but their use is generally discouraged. For more detailed information regarding SSL certificate considerations for DirectAccess IP-HTTPS click here.

Symantec Issued Certificates

Symantec is a popular commercial SSL certificate provider that has been commonly used for many years. However, due to integrity issues associated with their PKI management practices, Google and Mozilla announced they will soon be deprecating these certificates. This means users who browse to an HTTPS web site protected with a Symantec SSL certificate will receive a warning in their browser indicating the certificate is not trusted.

DirectAccess IP-HTTPS

It is important to note that there is no impact at all for DirectAccess when the server is configured to use an SSL certificate issued by Symantec. There is nothing you need to do to address this issue in this scenario. However, if a wildcard certificate is installed on the DirectAccess server and it is also used on other public-facing web servers in the organization, it is likely that the certificate will replaced, perhaps by another certificate provider. In this case, DirectAccess IP-HTTPS must be configured to use the new or updated SSL certificate.

Updating IP-HTTPS SSL Certificate

To update the DirectAccess IP-HTTPS SSL certificate, import the SSL certificate along with the private key in to the local computer certificate store on each DirectAccess server. Next identify the thumbprint of the new SSL certificate. Finally, open an elevated PowerShell command window and enter the following command.

$thumbprint = “ssl_cert_thumbprint”
$cert = Get-ChildItem -Path cert:\localmachine\my | where {$_.thumbprint -eq $thumbprint}
Set-RemoteAccess -SslCertificate $cert -PassThru

Be sure to replace “ssl_cert_thumbprint” with the actual thumbprint of your SSL certificate. 😉 In addition, for load-balanced and/or multisite deployments, run these PowerShell commands on each server in the enterprise.

Additional Information

SSL Certificate Considerations for DirectAccess IP-HTTPS

DirectAccess IP-HTTPS Null Cipher Suites Not Available 

DirectAccess IP-HTTPS Performance Issues

DirectAccess IP-HTTPS Performance Issues

DirectAccess IP-HTTPS Performance IssuesPerformance issues with DirectAccess are not uncommon. In fact, there are numerous threads on Microsoft and third-party forums where administrators frequently complain about slow download speeds, especially when using the IP-HTTPS IPv6 transition technology. Based on my experience the problem does not appear to be widespread but occurs with enough regularity that it is worthy of further investigation.

DirectAccess Design

The inherent design of DirectAccess is a major limiting factor for performance. DirectAccess uses a complex and heavy communication channel, with multiple layers of encapsulation, encryption, and translation. Fundamentally it is IPsec encrypted IPv6 traffic, encapsulated in HTTP, and then encrypted with Transport Layer Security (TLS) and routed over IPv4. It is then decrypted, decapsulated, decrypted again, then converted back to IPv4. The high protocol overhead incurred with multiple layers of encapsulation, encryption, and translation result in increased packet fragmentation, which further reduces performance.

DirectAccess Performance

Even under the best circumstances, DirectAccess performance is limited by many other factors, most notably the quality of the network connection between the client and the server. DirectAccess performs reasonably well over high bandwidth, low latency connections. However, network performance drops precipitously as latency increases and packet loss is encountered. This is to be expected given the design of the solution.

Intermediary Devices

It is not uncommon to find intermediary devices like firewalls, intrusion detection systems, malware scanners, and other security inspection devices limit the performance of DirectAccess clients. In addition, many security appliances have bandwidth caps enforced in software for licensing restrictions. Further, incorrect configuration of inline edge devices can contribute to increased fragmentation, which leads to poor performance as well.

Slow Downloads over IP-HTTPS

Many people report that download speeds seem to be artificially capped at 355Kbps. While this seems to be a display bug in the UI, there is plenty of evidence to indicate that, in some scenarios, DirectAccess is incapable of high throughput even over high-quality connections. Some who have deployed DirectAccess and VPN on the same server have reported that download speeds are only limited when using DirectAccess over IP-HTTPS and not with VPN using Secure Socket Tunneling Protocol (SSTP), which also uses TLS. This has led many to speculate that the issue is either a bug or a design flaw in the IP-HTTPS tunnel interface itself.

TCP Window Scaling Issues

In some of the network traces I’ve analyzed I’ve seen evidence that seems to support this theory. For example, a network trace taken when downloading a file over DirectAccess with IP-HTTPS showed the TCP window never scaled beyond 64K, which would seriously impede performance. Interestingly this doesn’t seem to happy when the client uploads files over IP-HTTPS. Clearly something unusual is happening.

Microsoft KB Article

Microsoft recently released a vaguely-worded KB article that appears to lend credence to some of these findings. The article seems to acknowledge the fact there are known issues with DirectAccess performance, but it lacks any specific details as to what the root cause is. Instead, it simply advises migrating to Windows 10 Always On VPN.

Summary

DirectAccess IP-HTTPS performance issues don’t appear to affect everyone, and the problem only seems to apply to file downloads and not to other types of traffic. However, there is mounting evidence of a systemic issue with DirectAccess performance especially over IP-HTTPS. Customers are advised to closely evaluate their uses cases for DirectAccess and if remote clients are frequently required to download large files over a DirectAccess connection, an alternative method of file transfer might be required. Optionally customers can consider evaluating alternative remote access solutions that offer better performance such as Windows 10 Always On VPN or third-party solutions such as NetMotion Mobility.

Additional Resources

Always On VPN and the Future of DirectAccess

What’s the Difference Between DirectAccess and Always On VPN?

NetMotion Mobility as an Alternative to Microsoft DirectAccess

DirectAccess NRPT Configuration with Split DNS

DirectAccess NRPT Configuration with Split DNSThe Name Resolution Policy Table (NRPT) in Windows provides policy-based name resolution request routing for DNS queries. DirectAccess uses the NRPT to ensure that only requests for resources in the internal namespace, as defined by the DirectAccess administrator, are sent over the DirectAccess connection. DNS queries for all other namespaces are sent to the DNS servers defined on the client’s network interface.

Note: This behavior changes when force tunneling is enabled. In this case, all DNS queries are sent over the DirectAccess connection with the exception of the NLS and the DirectAccess server’s public hostname(s). If force tunneling is enabled, the configuration guidance described below is not required.

Split DNS

NRPT configuration is straightforward when the internal and external namespaces are unique. However, when split DNS is used, meaning when the internal and external namespaces are the same, DirectAccess configuration is more challenging. Typically, there may be many resources that should not go over the DirectAccess connection, such as public-facing web servers, email and unified communications servers, federation servers, etc. Without additional configuration, requests for all of these services would go over the DirectAccess connection. That may or may not be desirable, depending on the requirements of the implementation.

DirectAccess Server

One crucial public resource is the DirectAccess server itself. When using split DNS, the DirectAccess implementation’s public hostname will, by default, be included in the internal namespace. In this scenario, the DirectAccess client will fail to establish a connection to the DirectAccess server.

Troubleshooting

When troubleshooting failed connectivity, the output of ipconfig will show the IP-HTTPS tunnel interface media state as “Media disconnected”.

DirectAccess NRPT Configuration with Split DNS

The output of Get-NetIPHttpsState will also return an error code 0x2AF9 with an interface status “Failed to connect to the IPHTTPS server; waiting to reconnect”.

DirectAccess NRPT Configuration with Split DNS

To further troubleshoot this issue, examine the output of Get-NetIPHttpsConfiguration. Test name resolution of the FQDN listed in the ServerURL field. If the issue is related to NRPT configuration, the client will fail to resolve this name to an IP address. Testing from a non-DirectAccess client should resolve correctly, however.

DirectAccess NRPT Configuration with Split DNS

NRPT Configuration

If split DNS is employed, it is necessary to include the DirectAccess server’s public hostname in the NRPT as an exemption. This will cause the DNS query for the public hostname to use public DNS servers, allowing the DirectAccess client to establish a connection successfully.

To resolve this issue, open the Remote Access Management console on the DirectAccess server, highlight DirectAccess and VPN under Configuration, and then click Edit on Step 3. Select DNS, and then double-click on an empty row in the table.

DirectAccess NRPT Configuration with Split DNS

Enter the public hostname for the DirectAccess deployment in the DNS suffix field (the public hostname can be found by clicking Edit on Step 2). Do NOT specify a DNS server. Click Apply, click Next twice, and then click Finish.

DirectAccess NRPT Configuration with Split DNS

Note: For multisite deployments, be sure to include the public hostname for each entry point in the enterprise. Also, if multisite is configured to use GSLB, include the GSLB hostname as well.

PowerShell

Alternatively, you can run the following PowerShell commands to automatically configure the NRPT for split DNS. For multisite deployments, be sure to run these commands on at least one DirectAccess server in each site.

$hostname = Get-RemoteAccess | Select-Object -ExpandProperty ConnectToAddress
Add-DAClientDnsConfiguration -DnsSuffix $hostname -PassThru

If multisite is configured to use GSLB, run the following PowerShell commands on one DirectAccess server in the enterprise.

$gslbfqdn = Get-DAMultiSite | Select-Object -ExpandProperty GslbFqdn
Add-DAClientDnsConfiguration -DnsSuffix $gslbfqdn -PassThru

Additional Information

Troubleshooting DirectAccess IP-HTTPS Error 0x2af9

DirectAccess DNS Not Working Properly

DirectAccess DNS Records Explained

Troubleshooting Name Resolution Issue on DirectAccess Clients

DirectAccess IP-HTTPS Null Cipher Suites Not Available

DirectAccess IP-HTTPS Null Cipher Suites Not AvailableMicrosoft first introduced support for null cipher suites for the IP-HTTPS IPv6 transition technology in Windows Server 2012, and it is supported for DirectAccess in Windows 8.x and Windows 10 clients. Using null cipher suites for IP-HTTPS eliminates the needless double encryption that occurs when using encrypted cipher suites. DirectAccess is a unique workload where SSL/TLS encryption isn’t really required because the payload being transported in HTTPS is already encrypted.

No Encryption by Design

When supporting Windows 8.x and Windows 10 clients, ensuring null cipher suites (TLS_RSA_WITH_NULL_SHA and TLS_RSA_WITH_NULL_SHA256) are enabled and operational is crucial to providing the highest levels of performance and scalability for the remote access solution. When following implementation best practices, this isn’t really an issue. However, in some cases null cipher suites may be disabled. This will result in reduced scalability and degraded performance for Windows 8.x and Windows 10 clients.

Validating SSL/TLS Configuration

The easiest way to verify that null cipher suites are being offered by the DirectAccess server is to use the Qualys SSL Labs server test site. Ideally you should see a result similar to this.

DirectAccess IP-HTTPS Null Cipher Suites Not AvailableFigure 1. Qualys SSL Labs server test site results for properly configured DirectAccess server.

Don’t be alarmed by the overall rating “F”. That happens because the Qualys test site is designed to test web servers where using null cipher suites would be a serious security issue. As I stated previously, the DirectAccess workload is unique in that its HTTPS payload is already encrypted, so using null cipher suites is acceptable in this scenario.

DirectAccess IP-HTTPS Null Cipher Suites Not AvailableFigure 2. Qualys SSL Labs server test site results for properly configured DirectAccess server showing support for null SSL/TLS cipher suites.

Null Cipher Suites Missing

When performing the Qualys SSL labs server test on a DirectAccess server, an overall rating of “A” is not desirable and indicates the DirectAccess server is misconfigured. This is caused by the lack of support for null cipher suites.

DirectAccess IP-HTTPS Null Cipher Suites Not AvailableFigure 3. Qualys SSL Labs server test site results for misconfigured DirectAccess server.

Common Causes

Null cipher suites for SSL and TLS can be disabled for a variety of reasons. Below are some of the most common causes for the lack of support for null cipher suites for DirectAccess.

Self-Signed Certificates – Using the Getting Started Wizard (simplified deployment) will configure DirectAccess using a self-signed certificate for IP-HTTPS. Using a self-signed certificate is discouraged for numerous reasons, most importantly because it disables support for null cipher suites.

Security Hardening – Security administrators may proactively disable support for null cipher suites in a misguided effort to “improve security” for DirectAccess. While this is acceptable and recommended on a web server, it is not advisable to disable null cipher suites on a DirectAccess server.

SSL Certificate Signing Algorithm – Using an SSL certificate signed with an Elliptical Curve (EC) key as opposed to an RSA key will result in the loss of support for null cipher suites for IP-HTTPS. High security/assurance certificates signed with EC keys are not recommended for use on DirectAccess servers and should be avoided if possible.

DirectAccess Configuration Options – Enabling One-Time Password (OTP) authentication on the DirectAccess server will also result in a loss of support for null cipher suites. Also, adding additional roles to the DirectAccess server such as client-based VPN or the Web Application Proxy (WAP) can also result in null cipher suites being disabled.

Summary

Null cipher suites are implemented by design on DirectAccess servers to enhance performance for Windows 8.x and Windows 10 clients and improve overall scalability for the implementation. They eliminate the pointless double encryption of DirectAccess communication, which itself is already encrypted. For optimal performance and scalability, be sure to follow implementation best practices and use a PKI-managed (public or private) SSL certificate signed with an RSA key (SHA-256 recommended). Resist the urge to “harden” the DirectAccess server by disabling support for null cipher suites, and avoid the use of SSL certificates signed with EC keys. In addition, carefully consider DirectAccess deployment options such as OTP authentication and consider deploying roles such as VPN and WAP on a separate server.

Additional Information

DirectAccess IP-HTTPS SSL and TLS Insecure Cipher Suites

DirectAccess IP-HTTPS Null Encryption and SSTP VPN

DirectAccess and FIPS Compliant Algorithms for Encryption

SSL Certificate Considerations for DirectAccess IP-HTTPS 

 

 

DirectAccess and FIPS Compliant Algorithms for Encryption

DirectAccess administrators may be required to enable Federal Information Processing Standards (FIPS) compliant algorithms for encryption, hashing, and signing on DirectAccess servers to meet certain regulatory and compliance requirements.

DirectAccess and FIPS Compliant Algorithms for Encryption

Performance Impact

Be advised that enabling this setting will disable support for null cipher suites for the IP-HTTPS IPv6 transition technology. This will result in the double encryption of all DirectAccess client communication, which will increase resource consumption on DirectAccess servers. This leads to reduced scalability and degraded performance for all DirectAccess clients, including Windows 8.x and Windows 10.

If enabling FIPS compliant cannot be avoided, additional compute capacity (CPU and memory) should be provisioned. For best results, add additional servers to distribute the workload and improve performance for DirectAccess clients.

Always On VPN

If you’re looking for better security and performance, consider migrating to Windows 10 Always On VPN. Always On VPN fully supports FIPS compliant algorithms without the negative performance impact associated with DirectAccess. If you’d like to learn more about security and Always On VPN, fill out the form below and I’ll get in touch with you.

Additional Resources

Always On VPN and the Future of DirectAccess 

5 Things DirectAccess Administrators Should Know About Always On VPN 

3 Important Advantages of Always On VPN over DirectAccess 

Outlook Offline over DirectAccess on Windows 10

Outlook Offline over DirectAccess on Windows 10You may encounter a scenario in which Outlook on Windows 10 reports that it is working offline while connected remotely via DirectAccess. The Network Connectivity Status Indicator (NCSI) shows DirectAccess is in a connected state and all other internal resources are accessible.

Outlook Offline over DirectAccess on Windows 10

This is caused by the default settings of the IP-HTTPS tunnel interface on the DirectAccess server not advertising a default route for connected DirectAccess clients. To resolve this issue, enable default route advertising for IP-HTTPS on each DirectAccess server in the enterprise by running the following PowerShell command.

Get-NetIPInterface | Where-Object {$_.InterfaceAlias -eq “IPHTTPSInterface”} | Set-NetIPInterface -AdvertiseDefaultRoute Enabled -PassThru

Outlook Offline over DirectAccess on Windows 10

In the past I’ve heard reports of this setting being overwritten after group policy refresh. Recent testing on Windows Server 2016 does not show this behavior, however. Please report any results you may have in the comments below. Thanks!

Top 5 DirectAccess Troubleshooting PowerShell Commands

Top 5 DirectAccess Troubleshooting PowerShell CommandsNative PowerShell commands in Windows 10 make DirectAccess troubleshooting much easier than older operating systems like Windows 7. For example, with one PowerShell command an administrator can quickly determine if a DirectAccess client has received the DirectAccess client settings policy. In addition, PowerShell can be used to view the status of the connection and retrieve additional information or error codes that can be helpful for determining the cause of a failed connection. Further, PowerShell can also be used to review configuration details and perform other troubleshooting and connectivity validation tasks.

Here are my top 5 PowerShell commands for troubleshooting DirectAccess on Windows 10.

1. Get-DAClientExperienceConfiguration

Ensuring that the DirectAccess Client Settings group policy has been applied to the client is one of the first steps in troubleshooting failed DirectAccess connections. While it is possible to use gpresult to do this, using the Get-DAClientExperienceConfiguration PowerShell command is much simpler. If DirectAccess client settings have been applied, the output of the command will include information such as the IPsec tunnel endpoint IPv6 addresses and the Network Connectivity Assistant (NCA) corporate resource URL. If DirectAccess client settings have not been applied, this information will be missing.

Top 5 DirectAccess Troubleshooting PowerShell Commands

Figure 1. DirectAccess Client Settings group policy successfully applied.

Top 5 DirectAccess Troubleshooting PowerShell Commands

Figure 2. DirectAccess Client Settings group policy not applied.

2. Get-NetIPHttpsState

Performance improvements first introduced in Windows 8 have made IP-HTTPS the IPv6 transition technology of choice when it comes to supporting DirectAccess client connectivity. Also, if the DirectAccess server is located behind an edge device performing Network Address Translation (NAT), IP-HTTPS is the only supported transition technology. Using the Get-NetIPHttpsState PowerShell command, the DirectAccess administrator can quickly determine if the IP-HTTPS connection was successful. If it was not, the command will return an error code and interface status that will indicate why the IP-HTTPS connection was unsuccessful.

Top 5 DirectAccess Troubleshooting PowerShell Commands

Figure 3. Get-NetIPHttpsState

3. Get-NetIPHttpsConfiguration

When troubleshooting IP-HTTPS connection failures, it is necessary to obtain additional information to continue the troubleshooting process. Using the Get-NetIPHttpsConfiguration PowerShell command, the DirectAccess administrator can obtain the public hostname for the DirectAccess server and ensure that the name resolves to the correct IP address in DNS and that it is reachable on TCP port 443.

Top 5 DirectAccess Troubleshooting PowerShell Commands

Figure 4. Get-NetIPHttpsConfiguration

4. Resolve-DnsName

Using the Resolve-DnsName PowerShell command is crucial when performing any name resolution tasks on the DirectAccess client. This is because Resolve-DnsName is aware of the Name Resolution Policy Table (NRPT) and will direct name resolution requests accordingly. Tools like nslookup are DNS server testing tools and are unaware of the NRPT. Typically they do not yield expected results when testing name resolution on a DirectAccess client.

Top 5 DirectAccess Troubleshooting PowerShell Commands

Figure 5. Name resolution results from Resolve-DnsName and nslookup.

5. Get-DnsClientNrptPolicy

Often the cause of DirectAccess client connectivity issues is a misconfigured NRPT. Using the Get-DnsClientNrptPolicy PowerShell command the DirectAccess administrator can validate that name resolution requests for host names in any internal namespaces are being sent to the DirectAccess DNS64 IPv6 address.

Top 5 DirectAccess Troubleshooting PowerShell Commands

Figure 6. Get-DnsClientNrptPolicy

Additional Resources

Top 5 DirectAccess Troubleshooting Tips

Troubleshooting Name Resolution Issues on DirectAccess Clients

Learn PowerShell in a Month of Lunches Book by Don Jones and Jeff Hicks

Implementing DirectAccess with Windows Server 2016 Book

Planning and Implementing DirectAccess with Windows Server 2016 Video Training Course

Managing and Supporting DirectAccess with Windows Server 2016 Video Training Course

 

 

DirectAccess Manage Out and System Center Configuration Manager (SCCM)

The seamless and transparent nature of DirectAccess makes it wonderfully easy to use. In most cases, it requires no user interaction at all to access internal corporate resources while away from the office. This enables users to be more productive. At the same time, it offers important connectivity benefits for IT administrators and systems management engineers as well.

Always Managed

DirectAccess Manage Out and System Center Configuration Manager (SCCM)DirectAccess clients are automatically connected to the corporate network any time they have a working Internet connection. Having consistent corporate network connectivity means they receive Active Directory group policy updates on a regular basis, just as on-premises systems do. Importantly, they check in with internal management systems such as System Center Configuration Manager (SCCM) and Windows Server Update Services (WSUS) servers, enabling them to receive updates in a timely manner. Thus, DirectAccess clients are better managed, allowing administrators to more effectively maintain the configuration state and security posture for all their managed systems, including those that are predominantly field-based. This is especially crucial considering the prevalence WannaCry, Cryptolocker, and a variety of other types of ransomware.

DirectAccess Manage Out

DirectAccess Manage Out and System Center Configuration Manager (SCCM)When manage out is configured with DirectAccess, hosts on the internal network can initiate connections outbound to remote connected DirectAccess clients. SCCM Remote Control and Remote Desktop Connection (RDC) are commonly used to remotely connect to systems for troubleshooting and support. With DirectAccess manage out enabled, these and other popular administrative tools such as VNC, Windows Remote Assistance, and PowerShell remoting can also be used to manage remote DirectAccess clients in the field. In addition, enabling manage out allows for the proactive installation of agents and other software on remote clients, such as the SCCM and System Center Operation Manager (SCOM) agents, third-party management agents, antivirus and antimalware software, and more. A user does not have to be logged on to their machine for manage out to work.

IPv6

DirectAccess manage out requires that connections initiated by machines on the internal network to remote-connected DirectAccess clients must be made using IPv6. This is because DirectAccess clients use IPv6 exclusively to connect to the DirectAccess server. To enable connectivity over the public IPv4 Internet, clients use IPv6 transition technologies (6to4, Teredo, IP-HTTPS), and IPv6 translation components on the server (DNS64 and NAT64) enable clients to communicate with internal IPv4 resources. However, DNS64 and NAT64 only translate IPv6 to IPv4 inbound. They do not work in reverse.

Native or Transition?

It is recommended that IPv6 be deployed on the internal network to enable DirectAccess manage out. This is not a trivial task, and many organizations can’t justify the deployment for just this one specific use case. As an alternative, IPv6 can be configured with an IPv6 transition technology, specifically the Intrasite Automatic Tunnel Addressing Protocol (ISATAP). ISATAP functions as an IPv6 overlay network, allowing internal hosts to obtain IPv6 addresses and routing information from an ISATAP router to support manage out for DirectAccess clients.

ISATAP

When DirectAccess is installed, the server is automatically configured as an ISATAP router. Guidance for configuring ISATAP clients can be found here. Using ISATAP can be an effective approach to enabling DirectAccess manage out for SCCM when native IPv6 is not available, but it is not without its drawbacks.

• Using the DirectAccess server for ISATAP is only supported with single server DirectAccess deployments.
• Using the DirectAccess server for ISATAP does work when using Network Load Balancing (NLB) with some additional configuration, but it is not supported.
• Using the DirectAccess server for ISATAP does not work when an external load balancer is used, or if multisite is enabled.

ISATAP with Load Balancing and Multisite

It is technically possible to enable DirectAccess manage out for SCCM using ISATAP in load-balanced and multisite DirectAccess deployments, however. It involves deploying a separate ISATAP router and some custom configuration, but once in place it works perfectly. I offer this service to my customers as part of a consulting engagement. If you’re interested in restoring DirectAccess manage out functionality to support SCCM remote control, RDC, or VNC in load-balanced or multisite DirectAccess deployments, fill out the form below and I’ll provide you with more information.

Additional Resources

ISATAP Recommendations for DirectAccess Deployments
DirectAccess Manage Out with ISATAP Fails on Windows 10 and Windows Server 2016
DirectAccess Client Firewall Rule Configuration for ISATAP Manage Out
Video: Windows 10 DirectAccess in action (includes manage out demonstration)

DirectAccess Troubleshooting with Nmap

DirectAccess IP-HTTPS Discovery Script for NmapDirectAccess troubleshooting can be made much easier using open source tools such as Nmap. Nmap can be used to perform many essential network connectivity and configuration checks, including validating network paths, confirming DirectAccess server response, and viewing SSL configuration. Nmap can also be used to ensure that the attack surface of the DirectAccess server is properly minimized. Some tests can be performed using only native Nmap functionality, while others require the use of specialized Nmap scripts that are included with the tool.

Installation

Nmap can be installed on a wide variety of operating systems, including Windows. If you plan to install Nmap on Windows, be sure to also install WinPcap and the Microsoft Visual C++ 2013 Redistributable. The Visual C++ component is included with the Nmap download. WinPcap must be downloaded separately here.

Testing External Connectivity

Validating external connectivity is often one of the first DirectAccess troubleshooting steps I take. Confirm that the DirectAccess public hostname resolves to the correct IP address, then run the following Nmap command to validate network connectivity from the Internet to the DirectAccess server.

nmap -n -Pn -p443 <da_public_hostname>

DirectAccess Troubleshooting with Nmap

If the hostname resolves correctly and the network path is complete, the server should respond and Nmap will show the port as open. However, this doesn’t necessarily mean that the DirectAccess server is the device that replied! Due to misconfiguration, it is possible that another server or network device listening on TCP port 443 responded, so this is not a conclusive test.

DirectAccess Server Response

To confirm the DirectAccess server is responding to HTTPS requests and not some other server or device, run the following Nmap command with the ip-https-discover script.

nmap -n -Pn -p443 <da_public_hostname> –script ip-https-discover

If the DirectAccess server responds to the request, Nmap will return the following message:

IP-HTTPS is supported. This indicates that this host supports Microsoft DirectAccess.

DirectAccess Troubleshooting with Nmap

If the port is open but the script does not return this message, it is likely that another server or device is responding on TCP port 443, not the DirectAccess server.

Note: If an Application Delivery Controller (ADC) is configured to perform IP-HTTPS preauthentication, the Nmap IP-HTTPS discovery script will not return this result. This is expected and by design.

SSL Certificate Validation

It is not uncommon for DirectAccess clients to fail to connect via IP-HTTPS because of SSL certificate issues. Specifically, an SSL certificate that is not trusted, is expired, or its subject field does not match the public hostname will prevent DirectAccess clients from connecting. To view the SSL certificate configuration of a DirectAccess server, run the following Nmap command with the ssl-cert script.

nmap -n -Pn -p443 <da_public_hostname> –script ssl-cert

DirectAccess Troubleshooting with Nmap

SSL Cipher Suite Configuration

Occasionally there can be issues with the SSL configuration on the DirectAccess server that prevent some clients from connecting, or result in poor performance. This commonly occurs when administrators perform SSL hardening on the DirectAccess server and remove support for null cipher suites. Null cipher suites should never be disabled on the DirectAccess server. They are important to ensure the highest levels of performance for Windows 8.x and Windows 10 clients. Also, if an Application Delivery Controller (ADC) or load balancer is performing SSL offload, lack of support for null cipher suites will prevent Windows 8.x and Windows 10 clients from connecting. To determine if the DirectAccess server supports null cipher suites, run the following Nmap command with the ssl-enum-ciphers script.

nmap -n -Pn -p443 <da_public_hostname> –script ssl-enum-ciphers

DirectAccess Troubleshooting with Nmap

Attack Surface Audit

If DirectAccess implementation and security best practices are followed, the DirectAccess server will be behind an edge firewall. The only port required to be allowed inbound for DirectAccess is TCP port 443. It is recommended that a full port scan be performed against the DirectAccess server’s public IPv4 address to identify any unnecessary ports that may be open externally. To perform a full port scan, run the following Nmap command.

nmap -n -Pn -p- <da_public_hostname>

Ideally it should look like this.

DirectAccess Troubleshooting with Nmap

If it looks something like this, you’re in serious trouble!

DirectAccess Troubleshooting with Nmap

The DirectAccess server should never be listening for requests other that HTTPS on the public Internet. Exposing services such as SMB (TCP port 445), RDP (TCP port 3389), and others presents a significant security risk. It is recommended that edge firewalls be configured to allow inbound TCP port 443 only. If the DirectAccess server is connected directly to the public Internet (not recommended!) then the Windows Firewall should be configured to restrict access to inbound TCP port 443 only.

Additional Resources

DirectAccess IP-HTTPS Discovery Script for Nmap
Planning and Implementing DirectAccess with Windows Server 2016 on Pluralsight
Implementing DirectAccess with Windows Server 2016 Book
DirectAccess Troubleshooting and Consulting Services

Troubleshooting DirectAccess IP-HTTPS Error Code 0x800b0109

A Windows 7 or Windows 8.x/10 client may fail to establish a DirectAccess connection using the IP-HTTPS IPv6transition technology. When troubleshooting this issue, running ipconfig.exe show 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 an error code of 0x800b0109 with an interface status Failed to connect to the IPHTTPS server; waiting to reconnect.

Troubleshooting DirectAccess IP-HTTPS Error 0x80090326

Error code 0x800b0109 translates to CERT_E_UNTRUSTEDROOT, indicating the client was unable to establish an IP-HTTPS connection because the certificate presented during the SSL handshake was issued by a certification authority that was not trusted. This commonly occurs when the DirectAccess server is configured with an SSL certificate issued by the internal PKI and DirectAccess clients are provisioned using offline domain join without using the /rootcacerts switch. This can also happen if DirectAccess is configured to use a self-signed certificate for IP-HTTPS, and the certificate is either renewed or DirectAccess is uninstalled and reinstalled.

Troubleshooting DirectAccess IP-HTTPS Error 0x800b0109

To resolve IP-HTTPS error code 0x800b0109, obtain the root certificate for the certificate authority that issued the SSL certificate used for IP-HTTPS and import it in to the DirectAccess client’s Trusted Root Certification Authorities local computer certificate store. Once complete, restart the IP helper service to reinitiate an IP-HTTPS connection.

Additional Information

Provisioning DirectAccess Clients using Windows Offline Domain Join

Troubleshooting DirectAccess IP-HTTPS Error Code 0x90320

Troubleshooting DirectAccess IP-HTTPS Error 0x2af9

DirectAccess Expired IP-HTTPS Certificate and Error 0x800b0101

SSL Certificate Considerations for DirectAccess IP-HTTPS

Implementing DirectAccess with Windows Server 2016

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