Welcome back fellow geek.  Today I’m continuing my deep dive series into AWS Managed Microsoft AD.  This will represent the seventh post in the series and I’ve covered some great content over the series including:

1. An overview of the service
2. How to setup the service
3. The directory structure, pre-configured security principals, group policies and the delegated security model
4. How to configure LDAPS and the requirements that pop up due to Amazon’s delegation model
5. Security of the service including supported secure transport protocols, ciphers, and authentication protocols
6. How do schema extensions work and what are the limitations

Today I’m going cover three additional capabilities of AWS Managed Microsoft AD which includes the creation of trusts, access to the Domain Controller event logs, and scalability.

I’ll first cover the capabilities around Active Directory trusts.  Providing this capability opens up the possibility a number of scenarios that aren’t possible in managed Windows Active Directory (Windows AD) services that don’t support trusts such as Microsoft’s Azure Active Directory Domain Services.  Some of the scenarios that pop up in my head are resource forest, trusts with trusted partners to maintain collaboration for legacy applications (applications dependent on legacy protocols such as Kerberos/NTLM/LDAP), trusts between development, QA, and production forests, and the usage of features features such as selective authentication to mitigate the risk to on-premises infrastructure.

For many organizations, modernization of an entire application catalog isn’t feasible but those organizations still want to take advantage of the cost and security benefits of cloud services.  This is where AWS Managed Microsoft AD can really shine.  It’s capability to support Active Directory forests trusts opens up the opportunity for those organizations to extend their identity boundary to the cloud while supporting legacy infrastructure.  Existing on-premises core infrastructure services such as PKI and SIEM can continue to be used and even extended to monitor the infrastructure using the managed Windows AD.

As you can see this is an extremely powerful capability and makes the service a good for almost every Windows AD scenario.  So that’s all well and good, but if you wanted marketing material you’d be reading the official documentation right?  You came here for the deep dive, so let’s get into it.

The first thing that popped into my mind was the question as to how Amazon would be providing this capability in a managed service model.  Creating a forest trust typically requires membership in privileged groups such as Enterprise Admins and Domain Admins, which obviously isn’t possible in a manged service.  I’m sure it’s possible to delegate the creation of Active Directory trusts and DNS conditional forwarders with modifications of directory permissions and possibly user rights, but there’s a better way.  What is this better way you may be asking yourself?  Perhaps serving it up via the Directory Services console in the same way schema modifications are served up?

Let’s walk through the process of setting up an Active Directory forest trust with a customer-managed traditional implementation of Windows Active Directory and an instance of AWS Managed Microsoft AD.  For this I’ll be leveraging my home Hyper-V lab.  I’m actually in the process of rebuilding it so there isn’t much there right now.  The home lab consists of two virtual machines, one named JOG-DC running Windows Server 2016 and functions as a domain controller (AD DS) and certificate authority (AD CS) for the journeyofthegeek.com Active Directory forest.  The other virtual machine is named named JOG-CLIENT, runs Windows 10, and is joined to the journeyofthegeek.com domain.  I’ve connected my VPC with my home lab using AWS’s Managed VPN to setup a site-to-site IPSec VPN connection with my local pfSense box.

Prior to setting up the trusts there are a few preparatory steps that need to be completed.  The steps will be familiar to those of you who have established forests trusts across firewalled network segments.  At a high level, you’ll want to perform the following tasks:

1. Ensure the appropriate ports are opened between the two forests.
2. Ensure DNS resolution between the two forests is established

For the first step I played it lazy since this is is a temporary configuration (please don’t do this in production).   I allowed all traffic from the VPC address range to my lab environment by modifying the firewall rules on my pfSense box.  On the AWS side I needed to adjust the traffic rules for the security group SERVER01 is in as well as the security group for the managed domain controllers.

To establish DNS resolution between the two forests I’ll be using conditional forwarders setup within each forest.  Setting the conditional forwarders up in the journeyofthegeek.com forest means I have to locate the IP addresses of the managed domain controllers in AWS.  There are a few ways you could do it, but I went to the AWS Directory Services Console and selected the geekintheweeds.com directory.

On the Directory details section of the console the DNS addresses list the IP addresses the domain controllers are using.

After creating the conditional forwarder in the DNS Management MMC in the journeyofthegeek.com forest, DNS resolution of a domain controller from geekintheweeds.com was successful.

I next created the trust in the journeyofthegeek.com domain ensuring to select the option to create the trust in this domain only and recording the trust password using the Active Directory Domains and Trusts.  We can’t create the trusts in both domains since we don’t have an account with the appropriate privileges in the AWS managed domain.

Next up I bounced back over to the Directory Services console and selected the geekintheweeds.com directory.  From there I selected the Network & security tab to open the menu needed to create the trust.

From here I clicked the Add trust relationship button which brings up the Add a trust relationship menu.  Here I filled in the name of the domain I want to establish the trust with, the trust password I setup in the journeyofthegeek.com domain, select a two-way trust, and add an IP that will be used within configuration of the conditional forwarder setup by the managed service.

After clicking the Add button the status of the trust is updated to Creating.

The process takes a few minutes after which the status reports as verified.

Opening up the Active Directory Users and Computers (ADUC) MMC in the journeyofthegeek.com domain and selecting the geekintheweeds.com domain successfully displays the directory structure.  Trying the opposite in the geekintheweeds.com domain works correctly as well.  So our two-way trust has been created successfully.  We would now have the ability to setup any of the scenarios I talked about earlier in the post including a resource forest or leveraging the managed domain as a primary Windows AD service for on-premises infrastructure.

The second capability I want to briefly touch on is the ability to view the Security Event Log and DNS Server logs on the managed domain controllers.  Unlike Microsoft’s managed Windows AD service, Amazon provides ongoing access to the Security Event Log and DNS Server Log.  The logs can be viewed using the Event Log MMC from a domain-joined machine or programmatically with PowerShell.  The group policy assigned to the Domain Controllers OU enforces a maximum event log size of 256MB but Amazon also archives a year’s worth of logs which can be requested in the event of an incident.  The lack of this capability was a big sore spot for me when I looked at Azure Active Directory Domain Services.  It’s great to see Amazon has identified this critical use case.

Last but definitely not least, let’s quickly cover the scalability of the service.  Follow Microsoft best practices and you can take full advantage of scaling horizontally with the click of a single button.  Be aware that the service only scales horizontally and not vertically.  If you have applications that don’t follow best practices and point to specific domain controllers or perform extremely inefficient LDAP queries (yes I’m talking to you developers who perform searches using front and rear-facing wildcards and use LDAP_MATCHING_RULE_IN_CHAIN filters) horizontal scaling isn’t going to help you.

Well folks that rounds out this entry into the series.  As we saw in the post Amazon has added key capabilities that Microsoft’s managed service is missing right now.  This makes AWS Managed Microsoft AD the more versatile of the two services and more than likely a better fit in almost any scenario where there is a reliance on Windows AD.

In my final posts of the series I’ll provide a comparison chart showing the differing capabilities of both AWS and Microsoft’s services.

See you next post!