14 min read

In this article by Jordan Krause, the author of the book Microsoft DirectAccess Best Practices and Troubleshooting, we will have a look at how Manage Out is configured to DirectAccess clients. DirectAccess is obviously a wonderful technology from the user’s perspective. There is literally nothing that they have to do to connect to company resources; it just happens automatically whenever they have Internet access. What isn’t talked about nearly as often is the fact that DirectAccess is possibly of even greater benefit to the IT department. Because DirectAccess is so seamless and automatic, your Group Policy settings, patches, scripts, and everything that you want to use to manage and manipulate those client machines is always able to run. You no longer have to wait for the user to launch a VPN or come into the office for their computer to be secured with the latest policies. You no longer have to worry about laptops being off the network for weeks at a time, and coming back into the network after having been connected to dozens of public hotspots while someone was on a vacation with it. While many of these management functions work right out of the box with a standard DirectAccess configuration, there are some functions that will need a couple of extra steps to get them working properly. That is our topic of discussion for this article.

We are going to cover the following topics:

  • Pulls versus pushes
  • What does Manage Out have to do with IPv6
  • Creating a selective ISATAP environment
  • Setting up client-side firewall rules
  • RDP to a DirectAccess client
  • No ISATAP with multisite DirectAccess

(For more resources related to this topic, see here.)

Pulls versus pushes

Often when thinking about management functions, we think of them as the software or settings that are being pushed out to the client computers. This is actually not true in many cases. A lot of management tools are initiated on the client side, and so their method of distributing these settings and patches are actually client pulls. A pull is a request that has been initiated by the client, and in this case, the server is simply responding to that request. In the DirectAccess world, this kind of request is handled very differently than an actual push, which would be any case where the internal server or resource is creating the initial outbound communication with the client, a true outbound initiation of packets. Pulls typically work just fine over DirectAccess right away. For example, Group Policy processing is initiated by the client. When a laptop decides that it’s time for a Group Policy refresh, it reaches out to Active Directory and says “Hey AD, give me my latest stuff”. The Domain Controllers then simply reply to that request, and the settings are pulled down successfully. This works all day, every day over DirectAccess. Pushes, on the other hand, require some special considerations. This scenario is what we commonly refer to as DirectAccess Manage Out, and this does not work by default in a stock DirectAccess implementation.

What does Manage Out have to do with IPv6?

IPv6 is essentially the reason why Manage Out does not work until we make some additions to your network. “But DirectAccess in Server 2012 handles all of my IPv6 to IPv4 translations so that my internal network can be all IPv4, right?” The answer to that question is yes, but those translations only work in one direction. For example, in our previous Group Policy processing scenario, the client computer calls out for Active Directory, and those packets traverse the DirectAccess tunnels using IPv6. When the packets get to the DirectAccess server, it sees that the Domain Controller is IPv4, so it translates those IPv6 packets into IPv4 and sends them on their merry way. Domain Controller receives the said IPv4 packets, and responds in kind back to the DirectAccess server. Since there is now an active thread and translation running on the DirectAccess server for that communication, it knows that it has to take those IPv4 packets coming back (as a response) from the Domain Controller and spin them back into IPv6 before sending across the IPsec tunnels back to the client. This all works wonderfully and there is absolutely no configuration that you need to do to accomplish this behavior.

However, what if you wanted to send packets out to a DirectAccess client computer from inside the network? One of the best examples of this is a Helpdesk computer trying to RDP into a DirectAccess-connected computer. To accomplish this, the Helpdesk computer needs to have IPv6 routability to the DirectAccess client computer. Let’s walk through the flow of packets to see why this is necessary. First of all, if you have been using DirectAccess for any duration of time, you might have realized by now that the client computers register themselves in DNS with their DirectAccess IP addresses when they connect. This is a normal behavior, but what may not look “normal” to you is that those records they are registering are AAAA (IPv6) records. Remember, all DirectAccess traffic across the internet is IPv6, using one of these three transition technologies to carry the packets: 6to4, Teredo, or IP-HTTPS. Therefore, when the clients connect, whatever transition tunnel is established has an IPv6 address on the adapter (you can see it inside ipconfig /all on the client), and those addresses will register themselves in DNS, assuming your DNS is configured to allow it.

When the Helpdesk personnel types CLIENT1 in their RDP client software and clicks on connect, it is going to reach out to DNS and ask, “What is the IP address of CLIENT1?” One of two things is going to happen. If that Helpdesk computer is connected to an IPv4-only network, it is obviously only capable of transmitting IPv4 packets, and DNS will hand them the DirectAccess client computer’s A (IPv4) record, from the last time the client was connected inside the office. Routing will fail, of course, because CLIENT1 is no longer sitting on the physical network. The following screenshot is an example of pinging a DirectAccess connected client computer from an IPv4 network:

How to resolve this behavior? We need to give that Helpdesk computer some form of IPv6 connectivity on the network. If you have a real, native IPv6 network running already, you can simply tap into it. Each of your internal machines that need this outbound routing, as well as the DirectAccess server or servers, all need to be connected to this network for it to work. However, I find out in the field that almost nobody is running any kind of IPv6 on their internal networks, and they really aren’t interested in starting now. This is where the Intra-Site Automatic Tunnel Addressing Protocol, more commonly referred to as ISATAP, comes into play. You can think of ISATAP as a virtual IPv6 cloud that runs on top of your existing IPv4 network. It enables computers inside your network, like that Helpdesk machine, to be able to establish an IPv6 connection with an ISATAP router. When this happens, that Helpdesk machine will get a new network adapter, visible via ipconfig / all, named ISATAP, and it will have an IPv6 address. Yes, this does mean that the Helpdesk computer, or any machine that needs outbound communications to the DirectAccess clients, has to be capable of talking IPv6, so this typically means that those machines must be Windows 7, Windows 8, Server 2008, or Server 2012. What if your switches and routers are not capable of IPv6? No problem. Similar to the way that 6to4, Teredo, and IP-HTTPS take IPv6 packets and wrap them inside IPv4 so they can make their way across the IPv4 internet, ISATAP also takes IPv6 packets and encapsulates them inside IPv4 before sending them across the physical network. This means that you can establish this ISATAP IPv6 network on top of your IPv4 network, without needing to make any infrastructure changes at all.

So, now I need to go purchase an ISATAP router to make this happen? No, this is the best part. Your DirectAccess server is already an ISATAP router; you simply need to point those internal machines at it.

Creating a selective ISATAP environment

All of the Windows operating systems over the past few years have ISATAP client functionality built right in. This has been the case since Vista, I believe, but I have yet to encounter anyone using Vista in a corporate environment, so for the sake of our discussion, we are generally talking about Windows 7, Windows 8, Server 2008, and Server 2012. For any of these operating systems, out of the box all you have to do is give it somewhere to resolve the name ISATAP, and it will go ahead and set itself up with a connection to that ISATAP router. So, if you wanted to immediately enable all of your internal machines that were ISATAP capable to suddenly be ISATAP connected, all you would have to do is create a single host record in DNS named ISATAP and point it at the internal IP address of your DirectAccess server. To get that to work properly, you would also have to tweak DNS so that ISATAP was no longer part of the global query block list, but I’m not even going to detail that process because my emphasis here is that you should not set up your environment this way.

Unfortunately, some of the step-by-step guides that are available on the web for setting up DirectAccess include this step. Even more unfortunately, if you have ever worked with UAG DirectAccess, you’ll remember on the IP address configuration screen that the GUI actually told you to go ahead and set ISATAP up this way.

Please do not create a DNS host record named ISATAP! If you have already done so, please consider this article to be a guide on your way out of danger.

The primary reason why you should stay away from doing this is because Windows prefers IPv6 over IPv4. Once a computer is setup with connection to an ISATAP router, it receives an IPv6 address which registers itself in DNS, and from that point onward whenever two ISATAP machines communicate with each other, they are using IPv6 over the ISATAP tunnel. This is potentially problematic for a couple of reasons. First, all ISATAP traffic default routes through the ISATAP router for which it is configured, so your DirectAccess server is now essentially the default gateway for all of these internal computers. This can cause performance problems and even network flooding. The second reason is that because these packets are now IPv6, even though they are wrapped up inside IPv4, the tools you have inside the network that you might be using to monitor internal traffic are not going to be able to see this traffic, at least not in the same capacity as it would do for normal IPv4 traffic.

It is in your best interests that you do not follow this global approach for implementing ISATAP, and instead take the slightly longer road and create what I call a “Selective ISATAP environment”, where you have complete control over which machines are connected to the ISATAP network, and which ones are not.

Many DirectAccess installs don’t require ISATAP at all. Remember, this is only used for those instances where you need true outbound reach to the DirectAccess clients. I recommend installing DirectAccess without ISATAP first, and test all of your management tools. If they work without ISATAP, great! If they don’t, then you can create your selective ISATAP environment.

To set ourselves up for success, we need to create a simple Active Directory security group, and a GPO. The combination of these things is going to allow us to decisively grant or deny access to the ISATAP routing features on the DirectAccess server.

Creating a security group and DNS record

First, let’s create a new security group in Active Directory. This is just a normal group like any other, typically a global or universal, whichever you prefer. This group is going to contain the computer accounts of the internal computers to which we want to give that outbound reaching capability. So, typically the computer accounts that we will eventually add into this group are Helpdesk computers, SCCM servers, maybe a management “jump box” terminal server, that kind of thing. To keep things intuitive, let’s name the group DirectAccess – ISATAP computers or something similar. We will also need a DNS host record created. For obvious reasons we don’t want to call this ISATAP, but perhaps something such as Contoso_ISATAP, swapping your name in, of course. This is just a regular DNS A record, and you want to point it at the internal IPv4 address of the DirectAccess server.

If you are running a clustered array of DirectAccess servers that are configured for load balancing, then you will need multiple DNS records. All of the records have the same name,Contoso_ISATAP, and you point them at each internal IP address being used by the cluster. So, one gets pointed at the internal Virtual IP (VIP), and one gets pointed at each of the internal Dedicated IPs (DIP). In a two-node cluster, you will have three DNS records for Contoso_ISATAP.

Creating the GPO

Now go ahead and follow these steps to create a new GPO that is going to contain the ISATAP connection settings:

  1. Create a new GPO, name it something such as DirectAccess – ISATAP settings.
  2. Place the GPO wherever it makes sense to you, keeping in mind that these settings should only apply to the ISATAP group that we created.
    • One way to manage the distribution of these settings is a strategically placed link.
    • Probably the better way to handle distribution of these settings is to reflect the same approach that the DirectAccess GPOs themselves take. This would mean linking this new GPO at a high level, like the top of the domain, and then using security filtering inside the GPO settings so that it only applies to the group that we just created. This way you ensure that in the end the only computers to receive these settings are the ones that you add to your ISATAP group.

I typically take the Security Filtering approach, because it closely reflects what DirectAccess itself does with GPO filtering. So, create and link the GPO at a high level, and then inside the GPO properties, go ahead and add the group (and only the group, remove everything else) to the Security Filtering section, like what is shown in the following screenshot:

Then move over to the Details tab and set the GPO Status to User configuration settings disabled.

Configuring the GPO

Now that we have a GPO which is being applied only to our special ISATAP group that we created, let’s give it some settings to apply. What we are doing with this GPO is configuring those computers which we want to be ISATAP-connected with the ISATAP server address with which they need to communicate , which is the DNS name that we created for ISATAP.

First, edit the GPO and set the ISATAP Router Name by configuring the following setting:

Computer Configuration | Policies | Administrative Templates | Network | TCPIP Settings | IPv6 Transition Technologies | ISATAP Router Name = Enabled (and populate your DNS record).

Second, in the same location within the GPO, we want to enable your ISATAP state with the following configuration:

Computer Configuration | Policies | Administrative Templates | Network | TCPIP Settings | IPv6 Transition Technologies | ISATAP State = Enabled State.

Adding machines to the group

All of our settings are now squared away, time to test! Start by taking a single computer account of a computer inside your network from which you want to be able to reach out to DirectAccess client computers, and add the computer account to the group that we created. Perhaps pause for a few minutes to ensure Active Directory has a chance to replicate, and then simply restart that computer. The next time it boots, it’ll grab those settings from the GPO, and reach out to the DirectAccess server acting as the ISATAP router, and have an ISATAP IPv6 connection. If you generate an ipconfig /all on that internal machine, you will see the ISATAP adapter and address now listed as shown in the following screenshot:

And now if you try to ping the name of a client computer that is connected via DirectAccess, you will see that it now resolves to the IPv6 record. Perfect! But wait, why are my pings timing out? Let’s explore that next.


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2 COMMENTS

  1. For some reason this is not working at all in my environment. External clients can access everything inside and ONLY my DA server can remote into those clients. I’m trying to set it up so other machine can access them as well. ISATAP is already on so I simply set the host name as per many tutorials online. My machines never get an IPv6.

    Description : ISATAP Configuration
    State : Enabled
    Router : 10.10.10.209
    ResolutionState : Default
    ResolutionIntervalSeconds : 60

    It doesn’t matter if I use IP or DNS resolution. Same outcome.

    I’m thinking my DA server somehow doesn’t have it’s routing setup properly? That is, it’s not setup to publish??? I dunno, I used the wizard to set it up and here I am.

  2. Hello

    I have DA working, even now pinging the client outside but still cannot use RDP or Powershell from the inside, it doesn’t get any reply back from the client.

    Do you have a second article following this one with more information about manage out? I dont see it.

    Thank you,

    Rod Green

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