Top 5 DirectAccess Troubleshooting Tips

Top 5 DirectAccess Troubleshooting TipsDirectAccess is a thing of beauty when everything is working as it should. When it isn’t, troubleshooting can be quite challenging. DirectAccess relies on many Windows platform technologies such as Active Directory for authentication, PKI for certificate management, group policy for settings deployment, IPsec for encryption, and IPv6 for transport. With so many dependencies, locating the source of the problem can be a difficult and daunting task.

I’m frequently called upon to help organizations of all sizes with DirectAccess troubleshooting. While this post is not intended to be a detailed, prescriptive guide for DirectAccess troubleshooting, I did want to share some common troubleshooting tips based on many years of troubleshooting DirectAccess.

Here are my top 5 DirectAccess troubleshooting tips:

  1. Check Prerequisites – Before diving in and collecting network traces and scouring event logs for clues as to why DirectAccess isn’t working, it’s essential to start at the beginning. Often the source of trouble is missing or misconfigured prerequisites. For example, is the DirectAccess client running a supported operating system? Remember, clients must be running Windows 10 Enterprise or Education, Windows 8.x Enterprise, or Windows 7 Enterprise or Ultimate. Also, ensure that the Windows firewall is enabled on DirectAccess servers and clients, that certificates are installed and valid (trusted, correct EKU, etc.), and that the DirectAccess settings GPO has been applied to servers and clients.
  2. Validate External Connectivity – If you are following implementation and security best practices for DirectAccess, the DirectAccess server will be in a perimeter/DMZ network behind an edge firewall. The firewall must be configured to allow inbound TCP port 443 only. If the firewall is also performing Network Address Translation (NAT), the NAT rule must be configured to forward traffic to the DirectAccess server’s dedicated or virtual IP address (VIP), or the VIP of the load balancer. Watch for routing issues when using load balancers too. It’s a good idea to confirm external connectivity using the Test-NetConnection PowerShell command. Even better, use the open source tool Nmap for more thorough testing.
  3. Remove Third Party Software – I can’t tell you how many times I’ve resolved DirectAccess connectivity issues by removing (not just disabling!) third party software on the client and/or server. It’s not uncommon for third-party security software to interfere with IPsec and/or IPv6 communication, both of which are vital to DirectAccess. If your DirectAccess troubleshooting efforts reveal no underlying issues with prerequisites or external connectivity, I’d suggest removing (at least temporarily) any third-party software and testing again.
  4. Isolate Environmental Issues – Occasionally other settings applied manually or via Active Directory group policy will interfere with DirectAccess. Examples include IPv6 being disabled in the registry, IPv6 transition technologies required to support DirectAccess are turned off, essential firewall rules for DirectAccess are disabled, or manipulating local security settings such as Access this computer from the network. To assist with troubleshooting it might be necessary to temporarily place DirectAccess clients and servers in their own dedicated Organizational Units (OUs) and block inheritance to isolate the configuration as much as possible. In addition, if DirectAccess clients are servers are provisioned using images or templates, testing with a clean build straight from the installation source (ISO or DVD) can be helpful.
  5. Check for Unsupported Configurations – If DirectAccess isn’t working, it might be possible the configuration you are trying to use is not supported. Examples including strong user authentication with OTP when force tunneling is enabled, provisioning Windows 7 clients when using Kerberos Proxy authentication, or provisioning Windows 10 clients when Network Access Protection (NAP) integration is enabled. These configurations won’t work and are formally documented here.

This is by no means a comprehensive or exhaustive troubleshooting guide. For more information and additional DirectAccess troubleshooting guidance I would encourage you to purchase my book Implementing DirectAccess with Windows Server 2016, which has an entire chapter devoted just to troubleshooting. In addition, watch my DirectAccess video training courses on Pluralsight for details and information about DirectAccess installation, configuration, management, support, and troubleshooting. And if you’re still struggling to resolve a DirectAccess problem, use the form at the bottom of this page to contact me to inquire about additional troubleshooting help.

Additional Resources

Microsoft Windows DirectAccess Client Troubleshooting Tool
DirectAccess and Windows 10 Professional
DirectAccess Troubleshooting with Nmap
DirectAccess Unsupported Configurations
Planning and Implementing DirectAccess with Windows Server 2016 Video Training Course on Pluralsight
Implementing DirectAccess with Windows Server 2016 Book

Need assistance with DirectAccess troubleshooting? Complete the form below and I’ll get in touch with you.

Deployment Considerations for DirectAccess on Amazon Web Services (AWS)

Organizations are rapidly deploying Windows server infrastructure with public cloud providers such as Amazon Web Services (AWS) and Microsoft Azure. With traditional on-premises infrastructure now hosted in the cloud, DirectAccess is also being deployed there more commonly.

Supportability

Interestingly, Microsoft has expressly stated that DirectAccess is not formally supported on their own public cloud platform, Azure. However, there is no formal statement of non-support for DirectAccess hosted on other non-Microsoft public cloud platforms. With supportability for DirectAccess on AWS unclear, many companies are taking the approach that if it isn’t unsupported, then it must be supported. I’d suggest proceeding with caution, as Microsoft could issue formal guidance to the contrary in the future.

DirectAccess on AWS

Deploying DirectAccess on AWS is similar to deploying on premises, with a few notable exceptions, outlined below.

IP Addressing

It is recommended that an IP address be exclusively assigned to the DirectAccess server in AWS, as shown here.

Deployment Considerations for DirectAccess on Amazon Web Services (AWS)

Prerequisites Check

When first configuring DirectAccess, the administrator will encounter the following warning message.

“The server does not comply with some DirectAccess prerequisites. Resolve all issues before proceed with DirectAccess deployment.”

The warning message itself states that “One or more network adapters should be configured with a static IP address. Obtain a static address and assign it to the adapter.

Deployment Considerations for DirectAccess on Amazon Web Services (AWS)

IP addressing for virtual machines are managed entirely by AWS. This means the DirectAccess server will have a DHCP-assigned address, even when an IP address is specified in AWS. Assigning static IP addresses in the guest virtual machine itself is also not supported. However, this warning message can safely be ignored.

No Support for Load Balancing

It is not possible to create load-balanced clusters of DirectAccess servers for redundancy or scalability on AWS. This is because enabling load balancing for DirectAccess requires the IP address of the DirectAccess server be changed in the operating system, which is not supported on AWS. To eliminate single points of failure in the DirectAccess architecture or to add additional capacity, multisite must be enabled. Each additional DirectAccess server must be provisioned as an individual entry point.

Network Topology

DirectAccess servers on AWS can be provisioned with one or two network interfaces. Using two network interfaces is recommended, with the external network interface of the DirectAccess server residing in a dedicated perimeter/DMZ network. The external network interface must use either the Public or Private Windows firewall profile. DirectAccess will not work if the external interface uses the Domain profile. For the Public and Private profile to be enabled, domain controllers must not be reachable from the perimeter/DMZ network. Ensure the perimeter/DMZ network cannot access the internal network by restricting network access in EC2 using a Security Group, or on the VPC using a Network Access Control List (ACL) or custom route table settings.

External Connectivity

A public IPv4 address must be associated with the DirectAccess server in AWS. There are several ways to accomplish this. The simplest way is to assign a public IPv4 address to the virtual machine (VM). However, a public IP address can only be assigned to the VM when it is deployed initially and cannot be added later. Alternatively, an Elastic IP can be provisioned and assigned to the DirectAccess server at any time.

An ACL must also be configured for the public IP that restricts access from the Internet to only inbound TCP port 443. To provide additional protection, consider deploying an Application Delivery Controller (ADC) appliance like the Citrix NetScaler or F5 BIG-IP to enforce client certificate authentication for DirectAccess clients.

Network Location Server (NLS)

If an organization is hosting all of its Windows infrastructure in AWS and all clients will be remote, Network Location Server (NLS) availability becomes much less critical than with traditional on-premises deployments. For cloud-only deployments, hosting the NLS on the DirectAccess server is a viable option. It eliminates the need for dedicated NLS, reducing costs and administrative overhead. If multisite is configured, ensure that the NLS is not using a self-signed certificate, as this is unsupported.

Deployment Considerations for DirectAccess on Amazon Web Services (AWS)

However, for hybrid cloud deployments where on-premises DirectAccess clients share the same internal network with cloud-hosted DirectAccess servers, it is recommended that the NLS be deployed on dedicated, highly available servers following the guidance outlined here and here.

Client Provisioning

All supported DirectAccess clients will work with DirectAccess on AWS. If the domain infrastructure is hosted exclusively in AWS, provisioning clients can be performed using Offline Domain Join (ODJ). Provisioning DirectAccess clients using ODJ is only supported in Windows 8.x/10. Windows 7 clients cannot be provisioned using ODJ and must be joined to the domain using another form of remote network connectivity such as VPN.

Additional Resources

DirectAccess No Longer Supported in Microsoft Azure

Microsoft Server Software Support for Azure Virtual Machines

DirectAccess Network Location Server (NLS) Guidance

DirectAccess Network Location Server (NLS) Deployment Considerations for Large Enterprises

Provisioning DirectAccess Clients using Offline Domain Join (ODJ)

DirectAccess SSL Offload and IP-HTTPS Preauthentication with Citrix NetScaler

DirectAccess SSL Offload and IP-HTTPS Preauthentication with F5 BIG-IP

Planning and Implementing DirectAccess with Windows Server 2016 Video Training Course

Implementing DirectAccess with Windows Server 2016 Book

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

Deploying DirectAccess in Microsoft Azure

Introduction

DirectAccess Now a Supported Workload in Microsoft AzureMany organizations are preparing to implement DirectAccess on Microsoft’s public cloud infrastructure. Deploying DirectAccess in Azure is fundamentally no different than implementing it on premises, with a few important exceptions (see below). This article provides essential guidance for administrators to configure this unique workload in Azure.

Important Note: There has been much confusion regarding the supportability of DirectAccess in Azure. Historically it has not been supported. Recently, it appeared briefly that Microsoft reversed their earlier decision and was in fact going to support it. However, the Microsoft Server Software Suport for Microsoft Azure Virtual Machines document has once again been revised to indicate that DirectAccess is indeed no longer formally supported on Azure. More details can be found here.

Azure Configuration

The following is guidance for configuring network interfaces, IP address assignments, public DNS, and network security groups for deploying DirectAccess in Azure.

Virtual Machine

Deploy a virtual machine in Azure with sufficient resources to meet expected demand. A minimum of two CPU cores should be provisioned. A VM with 4 cores is recommended. Premium storage on SSD is optional, as DirectAccess is not a disk intensive workload.

Network Interfaces

It is recommended that an Azure VM with a single network interface be provisioned for the DirectAccess role. This differs from on-premises deployments where two network interfaces are preferred because deploying VMs in Azure with two NICs is prohibitively difficult. At the time of this writing, Azure VMs with multiple network interfaces can only be provisioned using PowerShell, Azure CLI, or resource manager templates. In addition, Azure VMs with multiple NICs cannot belong to the same resource group as other VMs. Finally, and perhaps most importantly, not all Azure VMs support multiple NICs.

Internal IP Address

Static IP address assignment is recommended for the DirectAccess VM in Azure. By default, Azure VMs are initially provisioned using dynamic IP addresses, so this change must be made after the VM has been provisioned. To assign a static internal IP address to an Azure VM, open the Azure management portal and perform the following steps:

  1. Click Virtual machines.
  2. Select the DirectAccess server VM.
  3. Click Network Interfaces.
  4. Click on the network interface assigned to the VM.
  5. Under Settings click IP configurations.
  6. Click Ipconfig1.
  7. In the Private IP address settings section choose Static for the assignment method.
  8. Enter an IP address for the VM.
  9. Click Save.

Deploying DirectAccess in Microsoft Azure

Public IP Address

The DirectAccess VM in Azure must have a public IP address assigned to it to allow remote client connectivity. To assign a public IP address to an Azure VM, open the Azure management portal and perform the following steps:

  1. Click Virtual machines.
  2. Select the DirectAccess server VM.
  3. Click Network Interfaces.
  4. Click on the network interface assigned to the VM.
  5. Under Settings click IP configurations.
  6. Click Ipconfig1.
  7. In the Public IP address settings section click Enabled.
  8. Click Configure required settings.
  9. Click Create New and provide a descriptive name for the public IP address.
  10. Choose an address assignment method.
  11. Click Ok and Save.

Deploying DirectAccess in Microsoft Azure

Deploying DirectAccess in Microsoft Azure

Public DNS

If the static IP address assignment method was chosen for the public IP address, create an A resource record in public DNS that resolves to this address. If the dynamic IP address assignment method was chosen, create a CNAME record in public DNS that maps to the public hostname for the DirectAccess server. To assign a public hostname to the VM in Azure, open the Azure management portal and perform the following steps:

  1. Click Virtual machines.
  2. Select the DirectAccess server VM.
  3. Click Overview.
  4. Click Public IP address/DNS name label.Deploying DirectAccess in Microsoft Azure
  5. Under Settings click Configuration.
  6. Choose an assignment method (static or dynamic).
  7. Enter a DNS name label.
  8. Click Save.

Deploying DirectAccess in Microsoft Azure

Note: The subject of the SSL certificate used for the DirectAccess IP-HTTPS listener must match the name of the public DNS record (A or CNAME) entered previously. The SSL certificate does not need to match the Azure DNS name label entered here.

Network Security Group

A network security group must be configured to allow IP-HTTPS traffic inbound to the DirectAccess server on the public IP address. To make the required changes to the network security group, open the Azure management portal and perform the following steps:

  1. Click Virtual machines.
  2. Select the DirectAccess server VM.
  3. Click Network interfaces.
  4. Click on the network interface assigned to the VM.
  5. Under Settings click Network security group.
  6. Click the network security group assigned to the network interface.
  7. Click Inbound security rules.
  8. Click Add and provide a descriptive name for the new rule.
  9. Click Any for Source.
  10. From the Service drop-down list choose HTTPS.
  11. Click Allow for Action.
  12. Click Ok.

Deploying DirectAccess in Microsoft Azure

Note: It is recommended that the default-allow-rdp rule be removed if it is not needed. At a minimum, scope the rule to allow RDP only from trusted hosts and/or networks.

DirectAccess Configuration

When performing the initial configuration of DirectAccess using the Remote Access Management console, the administrator will encounter the following warning message.

“One or more network adapters should be configured with a static IP address. Obtain a static address and assign it to the adapter.”

Deploying DirectAccess in Microsoft Azure

This message can safely be ignored because Azure infrastructure handles all IP address assignment for hosted VMs.

The public name of the DirectAccess server entered in the Remote Access Management console must resolve to the public IP address assigned to the Azure VM, as described previously.

Deploying DirectAccess in Microsoft Azure

Additional Considerations

When deploying DirectAccess in Azure, the following limitations should be considered.

Load Balancing

It is not possible to enable load balancing using Windows Network Load Balancing (NLB) or an external load balancer. Enabling load balancing for DirectAccess requires changing static IP address assignments in the Windows operating system directly, which is not supported in Azure. This is because IP addresses are assigned dynamically in Azure, even when the option to use static IP address assignment is chosen in the Azure management portal. Static IP address assignment for Azure virtual machines are functionally similar to using DHCP reservations on premises.

Deploying DirectAccess in Microsoft Azure

Note: Technically speaking, the DirectAccess server in Azure could be placed behind a third-party external load balancer for the purposes of performing SSL offload or IP-HTTPS preauthentication, as outlined here and here. However, load balancing cannot be enabled in the Remote Access Management console and only a single DirectAccess server per entry point can be deployed.

Manage Out

DirectAccess manage out using native IPv6 or ISATAP is not supported in Azure. At the time of this writing, Azure does not support IPv6 addressing for Azure VMs. In addition, ISATAP does not work due to limitations imposed by the underlying Azure network infrastructure.

Summary

For organizations moving infrastructure to Microsoft’s public cloud, formal support for the DirectAccess workload in Azure is welcome news. Implementing DirectAccess in Azure is similar to on-premises with a few crucial limitations. By following the guidelines outlined in this article, administrators can configure DirectAccess in Azure to meet their secure remote access needs with a minimum of trouble.

Additional Resources

Implementing DirectAccess in Windows Server 2016
Fundamentals of Microsoft Azure 2nd Edition
Microsoft Azure Security Infrastructure
DirectAccess Multisite with Azure Traffic Manager
DirectAccess Consulting Services

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 da.richardhicks.net –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!

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