The Evolution of AD RMS to Azure Information Protection – Part 5 – Client-Side Migration and Testing

The Evolution of AD RMS to Azure Information Protection – Part 5 – Client-Side Migration and Testing

Welcome to the fifth entry in my series on the evolution of Microsoft’s Active Directory Rights Management Service (AD RMS) to Azure Information Protection (AIP).  We’ve covered a lot of material over this series.  It started with an overview of the service, examined the different architectures, went over key planning decisions for the migration from AD RMS to AIP, and left off with performing the server-side migration steps.  In this post we’re going to round out the migration process by performing a staged migration of our client machines.

Before we jump into this post, I’d encourage you to refresh yourself with my lab setup and the users and groups I’ve created, and finally the choices I made in the server side migration steps.  For a quick reference, here is the down and dirty:

  • Windows Server 2016 Active Directory forest named GEEKINTHEWEEDS.COM with servers running Active Directory Domain Services (AD DS), Active Directory Domain Name System (AD DNS), Active Directory Certificate Services (AD CS), Active Directory Federation Services (AD FS), Active Directory Rights Management Services (AD RMS), Azure Active Directory Connect, and Microsoft SQL Server Express.
  • Forest is configured to synchronize to Azure AD using Azure AD Connect and uses federated authentication via AD FS
  • Users Jason Voorhies and Ash Williams will be using a Windows 10 client machine with Microsoft Office 2016 named GWCLIENT1
  • Users Theodore Logan and Michael Myers will be using a Windows 10 client machine with Microsoft Office 2016 named GWCLIENT2
  • Users Jason Voorhies and Theodore Logan are in the Information Technology Windows Active Directory (AD) group
  • Users Ash Williams and Michael Myers are in the Accounting Windows AD group
  • Onboarding controls have been configured for a Windows AD group named GIW AIP Users of which Jason Voorhies and Ash Williams are members

Prepare The Client Machine

To take advantage of the new features AIP brings to the table we’ll need to install the AIP client. I’ll be installing the AIP client on GWCLIENT1 and leaving the RMS client installed by Office 2016 on GWCLIENT2. Keep in mind the AIP client includes the RMS client (sometimes referred to as MSIPC) as well.

If you recall from my last post, I skipped a preparation step that Microsoft recommended for client machines. The step has you download a ZIP containing some batch scripts that are used for performing a staged migration of client machines and users. The preparation script Microsoft recommends running prior to any server-side configuration Prepare-Client.cmd.  In an enterprise environment it makes sense but for this very controlled lab environment it wasn’t needed prior to server-side configuration. It’s a simple script that modifies the client registry to force the RMS client on the machines to go to the on-premises AD RMS cluster even if they receive content that’s been protected using an AIP subscription. If you’re unfamiliar with the order that the MSIPC client discovers an AD RMS cluster I did an exhaustive series a few years back.  In short, hardcoding the information to the registry will prevent the client from reaching out to AIP and potentially causing issues.

As a reminder I’ll be running the script on GIWCLIENT1 and not on GIWCLIENT2.  After the ZIP file is downloaded and the script is unpackaged, it needs to be opened with a text editor and the OnPremRMSFQDN and CloudRMS variables need to be set to your on-premises AD RMS cluster and AIP tenant endpoint. Once the values are set, run the script.

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Install the Azure Information Protection Client

Now that the preparation step is out of the way, let’s get the AIP client installed. The AIP client can be downloaded directly from Microsoft. After starting the installation you’ll first be prompted as to whether you want to send telemetry to Microsoft and use a demo policy.  I’ll be opting out of both (sorry Microsoft).

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After a minute or two the installation will complete successfully.

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At this point I log out of the administrator account and over to Jason Voorhies. Opening Windows Explorer and right-clicking a text file shows we now have the classify and protect option to protect and classify files outside of Microsoft Office.

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Testing the Client Machine Behavior Prior to Client-Side Configuration

I thought it would be fun to see what the client machine’s behavior would be after the AIP Client was installed but I hadn’t finished Microsoft’s recommended client-side configuration steps. Recall that GIWCLIENT1 has been previously been bootstrapped for the on-premises AD RMS cluster so let’s reset the client after observing the current state of both machines.

Notice on GWICLIENT1 the DefaultServer and DefaultServerUrl in the HKCU\Software\Microsoft\Office\16.0\Common\DRM do not exist even though the client was previously bootstrapped for the on-premises AD RMS instance. On GIWCLIENT2, which has also been bootstrapped, has the entries defined.

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I’m fairly certain AIP cleared these out when it tried to activate when I started up Microsoft Word prior to performing these steps.

Navigating to HKCU\Software\Classes\Local Settings\Software\Microsoft\MSIPC shows a few slight differences as well. On GIWCLIENT1 there are two additional entries, one for the discovery point for Azure RMS and one for JOG.LOCAL’s AD RMS cluster. The JOG.LOCAL entry exists on GIWCLIENT1 and not on the GIWCLIENT2 because of the baseline testing I did previously.

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Let’s take a look at the location the RMS client stores its certificates which is %LOCALAPPDATA%\Microsoft\MSIPC.  On both machines we see the expected copy of the public-key CLC certificate, the machine certificate, RAC, and use licenses for documents that have been opened.  Notice that even though the AD RMS cluster is running in Cryptographic Mode 1, the machine still generates a 2048-bit key as well.

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Now that the RMS Client is reset on GIWCLIENT1, let’s go ahead and see what happens the RMS client tries to do a fresh activation after having AIP installed but the client-side configuration not yet completed.

After opening Microsoft Word I select to create a new document. Notice that the labels displayed in the AIP bar include a custom label I had previously defined in the AIP blade.

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I then go back to the File tab on the ribbon and attempt to use the classic way of protecting a document via the Restrict Access option.

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After selecting the Connect to Rights Management Servers and get templates option the client successfully bootstraps back to the on-premises AD RMS cluster as can be seen from the certificates available to the client and that all necessary certificates were re-created in the MISPC directory.

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That’s Microsoft Office, but what about the scenario where I attempt to use the AIP client add in for Windows Explorer?

To test this behavior I created a PDF file named testfile.pdf.  Right-clicking and selecting the Classify and protect option opens the AIP client to display the default set of labels as well as a new GIW Accounting Confidential label.

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If I select that label and hit Apply I receive the error below.

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The template can’t be found because the client is trying to pull it from my on-premises AD RMS cluster.  Since I haven’t run the scripts to prepare the client for AIP, the client can’t reach the AIP endpoints to find the template associated with the label.

The results of these test tell us two things:

  1. Installing the AIP Client on a client machine that already has Microsoft Office installed and configured for an on-premises AD RMS cluster won’t break the client’s integration with that on-premises cluster.
  2. The AIP client at some point authenticated to the Geek In The Weeds Azure AD tenant and pulled down the classification labels configured for my tenant.

In my next post I’ll be examining these findings more deeply by doing a deep dive of the client behavior using a combination of procmon, Fiddler, and WireShark to analyze the AIP Client behavior.

Performing Client-Side Configuration

Now that the client has been successfully installed we need to override the behavior that was put in place with the Prepare-Client batch file earlier.  If we wanted to redirect all clients across the organization that were using Office 2016, we could use the DNS SRV record option listed in the migration article.  This option indicates Microsoft has added some new behavior to the RMS Client installed with Office 2016 such that it will perform a DNS lookup of the SRV record to see a migration has occurred.

For the purposes of this lab I’ll be using the Microsoft batch scripts I referenced earlier.  To override the behavior we put in place earlier with the Prepare-Client.cmd batch script, we’ll need to run both the Migrate-Client and Migrate-User scripts.  I created a group policy object (GPO) that uses security filtering to apply only to GIWCLIENT1 to run the Migrate-Client script as a Startup script and a GPO that uses security filtering to apply only to GIW AIP Users group which runs the Migrate-User script as a Login script.  This ensures only GIWCLIENT2 and Jason Voorhies and Ash Williams are affected by the changes.

You may be asking what do the scripts do?  The goal of the two scripts are to ensure the client machines the users log into point the users to Azure RMS versus an on-premises AD RMS cluster.  The scripts do this by adding and modifying registry keys used by the RMS client prior to the client searching for a service connection point (SCP).  The users will be redirected to Azure RMS when protecting new files as well as consuming files that were previously protected by an on-premises AD RMS cluster.  This means you better had performed the necessary server-side migration I went over previously, or else your users are going to be unable to consume previously protected content.

We’ll dig more into AIP/Office 2016 RMS Client discovery process in the next post.

Preparing Azure Information Protection Policies

Prior to testing the whole package, I thought it would be fun to create some AIP policies. By default, Microsoft provides you with a default AIP policy called the Global Policy. It comes complete with a reasonably standard set of labels, with a few of the labels having sublabels that have protection in some circumstances. Due to the migration path I undertook as part of the demo, I had to enabled protection for All Employees sublabels of both the Confidential and Highly Confidential labels.

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In addition to the global policy, I also created two scoped policies. One scoped policy applies to users within the GIW Accounting group and the other applies to users within the GIW Information Technology group. Each policy introduces another label and sublabel as seen in the screenshots below.

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Both of the sublabels include protection restricting members of the relevant groups to the Viewer role only. We’ll see these policies in action in the next section.

Testing the Client

Preparation is done, server-side migration has been complete, and our test clients and users have now been completed the documented migration process. The migration scripts performed the RMS client reset so no need to repeat that process.

For the first test, let’s try applying protection to the testfile.txt file I created earlier. Selecting the Classify and protect option opens up the AIP Client and shows me the labels configured in my tenant that support classification and protection. Recall from the AIP Client limitations different file types have different limitations. You can’t exactly append any type of metadata to content of a text file now can you?

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Selecting the IT Staff Only sublabel of the GIW IT Staff label and hitting the apply button successfully protects the text file and we see the icon and file type for the file changes.  Opening the file in Notepad now displays a notice the file is protected and the data contained in the original file has been encrypted.

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We can also open the file with the AIP Viewer which will decrypt the document and display the content of the text file.

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Next we test in Microsoft Word 2016 by creating a new document named AIP_GIW_ALLEMP and classifying it with the High Confidential All Employees sublabel.  The sublabel adds protection such that all users in the GIW Employees group have Viewer rights.

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Opening the AIP_GIW_ALLEMP Word document that was protected by Jason Voorhies is successful and it shows Ash Williams has viewer rights for the file.

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Last but not least, let’s open the a document we previously protected with AD RMS named GIW_GIWALL_ADRMS.DOCX.  We’re able to successfully open this file because we migrated the TPD used for AD RMS up to AIP.

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At this point we’ve performed all necessary steps up the migration.  What you have left now is cleanup steps and planning for how you’ll complete the rollout to the rest of your user base.  Not bad right?

Over the next few posts ‘ll be doing a deep dive of the RMS Client behavior when interacting with Azure Information Protection.   We’ll do some procmon captures to the behavior of the client when it’s performing its discovery process as well as examining the web calls it makes to Fiddler.  I’ll also spend some time examining the AIP blade and my favorite feature of AIP, Tracking and Revocation.

See you next time!

 

The Evolution of AD RMS to Azure Information Protection – Part 4 – Preparation and Server-Side Migration

The Evolution of AD RMS to Azure Information Protection – Part 4 – Preparation and Server-Side Migration

The time has finally come to get our hands dirty.  Welcome to my fourth post on the evolution of Active Directory Rights Management Service (AD RMS) to Azure Information Protection (AIP).  So far in this series I’ve done an overview of the service, a comparison of the architectures, and covered the key planning decisions that need to place when migrating from AD RMS to AIP.  In this post I’ll be performing the preparation and server-side migration steps for the migration from AD RMS to AIP.

Microsoft has done a wonderful job documenting the steps for the migration from AD RMS to AIP within the migration guide.  I’ll be referencing back to the guide as needed throughout the post.  Take a look at my first post for a refresher of my lab setup.  Take note I’ll be migrating LAB2 and will be leaving LAB1 on AD RMS.  Here are some key things to remember about the lab:

  • There is a forest trust between the JOG.LOCAL and GEEKINTHEWEEDS.COM Active Directory Forests
  • AD RMS Trusted User Domains (TUDs) have been configured on both JOG.LOCAL and GEEKINTHEWEEDS.COM

I’ve created the following users, groups, and AD RMS templates (I’ve been on an 80s/90s movies fix, so enjoy the names).

  • GEEKINTHEWEEDS.COM CONFIGURATION
    • (User) Jason Voorhies
      • User Principal Name Attribute: jason.voorhies@geekintheweeds.com
      • Mail Attribute: jason.voorhies@geekintheweeds.com
      • Group Memberships: Domain Users, GIW Employees, Information Technology
    • (User) Theodore Logan
      • User Principal Name Attribute: theodore.logan@geekintheweeds.com
      • Mail Attribute: theodore.logan@geekintheweeds.com
      • Group Memberships: Domain Users, GIW Employees, Information Technology
    • (User) Ash Williams
      • User Principal Name Attribute: jason.voorhies@geekintheweeds.com
      • Mail Attribute: ash.williams@geekintheweeds.com
      • Group Memberships: Domain Users, GIW Employees, Accounting
    • (User) Michael Myers
      • User Principal Name Attribute: michael.myers@geekintheweeds.com
      • Mail Attribute: michael.myers@geekintheweeds.com
      • Group Memberships: Domain Users, GIW Employees, Accounting
    • (Group) Accounting
      • Mail Attribute: giwaccounting@geekintheweeds.com
      • Group Type: Universal Distribution
    • (Group) GIW Employees
      • Mail Attribute: giwemployees@geekintheweeds.com
      • Group Type: Universal Distribution
    • (Group) Information Technology
      • Mail Attribute: giwit@geekintheweeds.com
      • Group Type: Universal Distribution
    • (Group) GIW AIP Users
      • Group Type: Global Security
    • (AD RMS Template) GIW Accounting
      • Users: giwaccounting@geekintheweeds.com
      • Rights: Full Control
    • (AD RMS Template) GIW Employees
      • Users: giwemployees@geekintheweeds.com
      • Rights: View, View Rights
    • (AD RMS Template) GIW IT
      • Users: giwit@geekintheweeds.com
      • Rights: Full Control
  • JOG.LOCAL CONFIGURATION

    • (User) Luke Skywalker
      • User Principal Name Attribute: luke.skywalker@jog.local
      • Mail Attribute: luke.skywalker@jog.local
      • Group Memberships: Domain Users, jogemployees
    • (User) Han Solo
      • User Principal Name Attribute: han.solo@jog.local
      • Mail Attribute: han.solo@jog.local
      • Group Memberships: Domain Users, jogemployees
    • (Group) jogemployees
      • Mail Attribute: jogemployees@jog.local
      • Group Type: Universal Distribution

After my lab was built I performed the following tests:

  • Protected Microsoft Word document named GIW_LS_ADRMS with GEEKINTHEWEEDS.COM AD RMS Cluster and successfully opened with Luke Skywalker user from JOG.LOCAL client machine.
  • Protected Microsoft Word document named GIW_GIWALL_ADRMS with GEEKINTHEWEEDS.COM AD RMS Cluster and GIW Employees template and unsuccessfully opened with Luke Skywalker user from JOG.LOCAL client machine.
  • Protected Microsoft Word document named GIW_JV_ADRMS with GEEKINTHEWEEDS.COM AD RMS Cluster using Theodore Logan user and opened successfully with Jason Voorhies user from GEEKINTHEWEEDS.COM client machine.
  • Protected Microsoft Word document named JOG_MM_ADRMS with JOG.LOCAL AD RMS Cluster using Luke Skywalker user and opened successfully with Michael Myers user from GEEKINTHEWEEDS.COM client machine.
    Protected Microsoft Word document named GIW_ACCT_ADRMS with GEEKINTHEWEEDS.COM AD RMS Cluster and GIW Accounting template and was unsuccessful in opening with Jason Voorhies user from GEEKINTHEWEEDS.COM client machine.

These tests verified both AD RMS clusters were working successfully and the TUD was functioning as expected.  The lab is up and running, so now it’s time to migrate to AIP!

Our first step is to download the AADRM PowerShell module from Microsoft.  I went the easy route and used the install-module cmdlet.

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Back in March Microsoft announced that AIP would be enabled by default on any eligible tenants with O365 E3 or above that were added after February.  Microsoft’s migration guide specifically instructs you to ensure protection capabilities are disabled if you’re planning a migration from AD RMS to AIP.  This means we need to verify that AIP is disabled.  To do that, we’re going to use the newly downloaded AADRM module to verify the status.

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As expected, the service is enabled.  We’ll want to disable the service before beginning the migration process by running the Disable-Aadrm cmdlet.  After running the command, we see that the functional state is now reporting as disabled.

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While we have the configuration data up we’re going to grab the value (minus _wmcs/licensing) in the  LicensingIntranetDistributionPointUrl property.  We’ll be using this later on in the migration process.

In most enterprise scenarios you’d want to perform a staged migration process of your users from AD RMS to AIP.  Microsoft provides for this with the concept of onboarding controls.  Onboarding controls allow you to manage who has the ability to protect content using AIP even when the service has been enabled at the tenant level.  Your common use case would be creating an Azure AD-managed or Windows AD-synced group which is used as your control group.  Users who are members of the group and are licensed appropriately would be able to protect content using AIP.  Other users within the tenant could consume the content but not protect it.

In my lab I’ll be using the GIW AIP Users group that is being synchronized to Azure AD from my Windows AD as the control group.  To use the group I’ll need to get its ObjectID which is the object’s unique identifier in Azure AD.  For that I used the Get-AzureADGroup cmdlet within Azure AD PowerShell module.

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Microsoft’s migration guide next suggests come configuration modifications to Windows computers within the forest.  I’m going to hold off on this for now and instead begin the server-side migration steps.

First up we’re going to export the trusted publisher domains (TPDs) from the AD RMS cluster.  We do this to ensure that users that have migrated over to AIP are still able to open content that was previously protected by the AD RMS cluster.  The TPD includes the Server Licensor Certificate (SLC) keys so when exporting them we protect them with a password and create an XML file that includes the SLC keys and any custom AD RMS rights policy templates.

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Next we import the exported TPD to AIP using the relevant process based upon how we chose to protect the cluster keys.  For this lab I used a software key (stored in the AD RMS database) so I’ll be using the software key to software key migration path.  Thankfully this path is quite simple and consists of running another cmdlet from the AADRM PowerShell module.  In the first command we store the password used to protect the TPD file as a secure string and use the Import-AadrmTpd cmdlet to pull it into AIP.  Notice the resulting data provides the cluster friendly name, indicates the Cryptographic Mode was set to 1, the key was a Microsoft-managed (aka software key) and there were three rights policy templates attached to the TPD.

Keep in mind that if you have multiple TPDs for some reason (let’s say you migrated from Cryptographic Mode 1 to Cryptographic Mode 2) you’ll need to upload each TPD separately and set the active TPD using the Set-AadrmKeyProperties cmdlet.

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Running a Get-AadrmTemplate shows the default templates Microsoft provides you with as well as the three templates I had configured in AD RMS.

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The last step of the server side of the process is to activate AIP.  For that we use the Enable-Aadrm cmdlet from the AADRM PowerShell module.

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At this point the server-side configuration steps have been completed and AIP is ready to go.  However, we still have some very important client-side configuration steps to perform.  We’ll cover those steps in my post.

Have a great week!

The Evolution of AD RMS to Azure Information Protection – Part 3 – Planning The Migration

The Evolution of AD RMS to Azure Information Protection – Part 3 – Planning The Migration

Welcome to the third post in my series exploring the evolution of Active Directory Rights Management Service (AD RMS) into Azure Information Protection (AIP).  My first post provided an overview of the service and some of its usages and my second post covered how the architecture of the solution has changed as the service has shifted from traditional on-premises infrastructure to  a software-as-a-service (SaaS) offering).  Now that we understand the purpose of the service and its architecture, let’s explore what a migration will look like.

For the post I’ll be using the labs I discussed in my first post.  Specifically, I’ll be migrating lab 2 (the Windows Server 2016 lab) from using AD RMS to Azure Information Protection.  I’ve added an additional Windows 10 Professional machine to that lab for reasons I’ll discuss later in the post.  The two Windows 10 machines are named CLIENT1 and CLIENT2.  Microsoft has assembled some guidance which I’ll be referencing throughout this post and using as the map for the migration.

With the introduction done, let’s dig in.

Before we do any button pushing, there’s some planning necessary to ensure a successful migration.  The key areas of consideration are:

  • Impact to collaboration with trusted organizations
  • Tenant key storage
  • AIP Client Rollout
  • Integrated Rights Management (IRM) functionality of Microsoft Exchange Server or Microsoft SharePoint Server

Impact to collaboration with trusted organizations

Possibly most impactful to an organization is the planning that goes into how the migration will affect collaboration with partner organizations.  Back in the olden days of on-premises AD RMS, organizations would leverage the protection and control that came with AD RMS to collaborate with trusted partners.  This was accomplished through trusted user domains (TUDs) or federated trusts.  With AIP the concept of TUDs and additional infrastructure to support federated trusts is eliminated and instead replaced with the federation capabilities provided natively via Azure Active Directory.

Yes folks, this means that if you want the same level of collaboration you had with AD RMS using TUDs, both organizations will need to need to have an Azure Active Directory (Azure AD) tenant with a license that supports the Azure Rights Management Service (Azure RMS).    In a future post in the series, we’ll check out what happens when the partner organization doesn’t migrate to Azure AD and attempts to consume the protected content.

Tenant Key Storage

The tenant key can be thought to as the key to the kingdom in the AIP world.  For those of you familiar with AD RMS, the tenant key serves the same function as the cluster key. In the on-premises world of AD RMS the cluster key was either stored within the AD RMS database or on a hardware security module (HSM).

When performing a migration to the world of AIP, storage of the tenant key has a few options.  If you’re using a cluster key that was stored within the AD RMS database you can migrate the key using some simple PowerShell commands.  If you’re opted to use HSM storage for your cluster key, you’re going to be looking at the bring your own key (BYOK) scenario.  Finally, if you have a hard requirement to keep the key on premises you can explore the hold your own key option (HYOK).

For this series I’ve configured my labs with a cluster key that is stored within the AD RMS database (or software key as MS is referring to it).  The AD RMS cluster in my environment runs in cryptographic mode 1, so per MS’s recommendation I won’t be migrating to cryptographic mode 2 until after I migrate to AIP.

AIP Client Rollout

Using AIP requires the AIP Client be installed.  The AD RMS Client that comes with pre-packaged with Microsoft Office can protect but can’t take advantage of the labels and classification features of AIP.   You’ll need to consider this during your migration process and ensure any middleware that uses the AD RMS Client is compatible with the AIP Client.  The AIP Client is compatible with on-premises AD RMS so you don’t need to be concerned with backwards compatibility.

As I mentioned above, I have two Windows 10 clients named CLIENT1 and CLIENT2.  In the next post I’ll be migrating CLIENT2 to the AIP Client and keeping CLIENT1 on the AD RMS Client.  I’ll capture and break down the calls with Fiddler so we can see what the differences are.

Integrated Rights Management (IRM) functionality of Microsoft Exchange Server or Microsoft SharePoint Server

If you want to migrate to AIP but still have a ways to go before you can migrate Exchange and SharePoint to the SaaS counterparts, have no fear.  You can leverage the protection capabilities of AIP (aka Azure RMS component) by using the Microsoft Rights Management Service Connector.  The connector requires some light weight infrastructure to handle the communication between Exchange/SharePoint and AIP.

I probably won’t be demoing the RMS Connector in this series, so take a read through the documentation if you’re curious.

We’ve covered an overview of AIP, the different architectures of AD RMS and AIP, and now have covered key planning decisions for a migration.  In the next post in my series we’ll start getting our hands dirty by initiating the migration from AD RMS to AIP.  Once the migration is complete, I’ll be diving deep into the weeds and examining the behavior of the AD RMS and AIP clients via Fiddler captures and AD RMS client debugging (assuming it still works with the AIP client).

See you next post!

The Evolution of AD RMS to Azure Information Protection – Part 2 – Architecture

The Evolution of AD RMS to Azure Information Protection – Part 2 – Architecture

Hi there.  Welcome to the second post in my series exploring the evolution of Active Directory Rights Management Service (AD RMS) into Azure Information Protection (AIP).  In the first post of the series I gave an brief overview of the important role AIP plays in Microsoft’s Cloud App Security (CAS) offering.  I also covered the details of the lab I will be using for this series.  Take a few minutes to read the post to familiarize yourself with the lab details because it’ll be helpful as we progress through the series.

I went back and forth as to what topic I wanted to cover for the second post and decided it would be useful to start at the high level comparing the components in a typical Windows AD RMS implementation to those used when consuming AIP.  I’m going to keep the explanation of each component brief to avoid re-creating existing documentation, but I will provide links to official Microsoft document for each component I mention.  With that intro, let’s begin.

The infrastructure required in an AD RMS implementation is pretty minimal but the complexity is in how all of the components work together to provide the solution.  At a very high level it is similar to any other web-based application consisting of a web server, application code, and a data backend.   The web-based application integrated with a directory to authenticate users and get information about the user that is used in authorization decisions.  In the AD RMS world the components map to the following products:

  • Web Server – Machine running Windows Server with Microsoft Internet Information Services and Microsoft Message Queuing Service
  • Application Code – Code installed onto the machine after adding the AD RMS role to a machine running Windows Server
  • Data Backend – Machine running Windows Server with Microsoft SQL Server running on it hosting configuration and logging database (optionally Windows Internal Database (WID) for test environments)
  • Directory – Windows Active Directory provides authentication, user information used for authorization, and stores additional AD RMS configuration data (Service Connection Point)

Nodes providing the AD RMS service are organized into a logical container called an AD RMS Cluster. Like most web applications AD RMS can be scaled out by adding more nodes to the cluster to improve performance and provide high availability (HA).  If using MS SQL for the data backend, traditional methods of HA can be used such as SQL clustering, database mirroring, and log shipping.  You can plop your favorite load balancer in front of the solution to help distribute the application load and keep track of the health of the nodes providing the service.

Beyond the standard web-based application components we have some that are specific to AD RMS.  Let’s take a deeper look at them.

  • AD RMS Cluster Key

    The AD RMS cluster key is the most critical part of an AD RMS implementation, the “key to the kingdom”, as it is used to sign the Server Licensor Certificate (SLC) which contains the corresponding public key.  The SLC is used to sign certificates created by AD RMS that allow for consumption of AD RMS-protected content as well as being used by AD RMS clients to encrypt the content key when a document is newly protected by AD RMS.

    The AD RMS cluster key is shared by all nodes that are members of the AD RMS cluster.  It can be stored within the MS SQL database/WID or on a supported hardware security module for improved security.

  • AD RMS Client / AD RMS-Integrated Server Applications

    Applications are great, but you need a method to consume them.  Once content is protected by AD RMS it can only be consumed by an application capable of communicating with AD RMS.  In most cases this is accomplished by using an application that has been written to use the AD RMS Client.  The AD RMS Client comes pre-installed on Windows Vista and up desktop operating systems and Windows Server 2008 and up server operating systems.

    The AD RMS client performs tasks such as bootstrapping (sometimes referred to as activation).  I won’t go into the details because I wouldn’t do near as well job as Dan does in the bootstrapping link.  In short it generates some keys and obtains some certificates from the AD RMS service that facilitate protecting and consuming content.

    AD RMS-integrated server applications such as Microsoft SharePoint Server and Microsoft Exchange Server provide server-level services that leverage the capabilities provided by AD RMS to protect data such as files stored in a SharePoint library or emails sent through Microsoft Exchange.

  • AD RMS Policy Templates

    While not a component of the system architecture, AD RMS Policy Templates are an AD RMS concept that deserves mention in this discussion.  The templates can be created by an organization to provide a standard set of use rights applicable to a type of data.  Common use cases are having multiple templates created for different data types.  For example, you may want one data type that allows trusted partners to view the document but not print or forward it while another template may restrict view rights to the accounting department.

    In AD RMS the policies are stored in the AD RMS database but are accessible via a call to the web service.  Optionally they can be exported from the database and distributed in other means like a Windows file share.

As you can see there are a lot of moving parts to an on-premises Windows AD RMS implementation.  Some of the components mentioned above can get even more complicated when the need to collaborate across organizations or support mobile devices arises.

How does AIP compare?  For the purposes of this post, I’m going to focus that comparison on Azure RMS which provides the protection capability of AIP.  Azure RMS is a software-as-a-service (SaaS) offering from Microsoft replaces (yes Microsoft, let’s be honest here) AD RMS.  It is licensed on a per user basis via a stand-alone, Enterprise Mobility + Security P1/P2, or qualifying Office 365 license.

The architecture of Azure RMS is far more simple than what existed for AD RMS.  Like most SaaS services, there is no on-premises infrastructure required except in very specific scenarios such as hold-your-own-key (HYOK) or integrating Azure RMS with an on-premises Microsoft Exchange Server, Microsoft SharePoint Server, or servers running Windows Server and File Classification Infrastructure (FCI) using the RMS Connector.   This means you won’t be building any servers to hold the RMS role or SQL Servers to host configuration and logging information.  The infrastructure is now managed by Microsoft and the RMS service provided over HTTP/HTTPS.

Azure RMS shifts its directory dependency to Azure Active Directory (AAD).  It uses the tenant in which the Azure RMS licenses are associated with for authentication and authorization of users.  As with any AAD use case, you can still authenticate users against your on-premises Windows Active Directory if you’ve configured your tenant for federated authentication and source data from an on-premises directory using Azure Active Directory Connect.

The cluster key, client, integrated applications, and policies are still in place and work similar to on-premises AD RMS with some changes to both function and names.

  • Azure Information Protection Tenant Key

    The AD RMS Cluster key has been renamed to the Azure Information Protection tenant key.  The tenant key serves the same purpose as the AD RMS Cluster and is used to sign the SLC certificate and decrypt information sent to Azure RMS using the public key in the SLC.  The differences between the two are really around how the key is generated and stored.  By default the tenant key is generated (note that Microsoft generates a 2048-bit key instead of a 1024-bit like was done with new installations of AD RMS) by Microsoft and is associated with your Azure Active Directory tenant.  Other options include bring-your-own-key (BYOK), HYOK, and a special instance where you are migrating from AD RMS to Azure RMS.  I’ll cover HYOK and the migration instance in future posts.

  • Azure Information Protection Client

    The AD RMS client is replaced with the Azure Information Protection Client.  The client performs the same functions as the AD RMS Client but allowing for integration with either on-premises AD RMS or Azure RMS.  In addition, the client introduces functionality around Azure Information Protection including adding a classification bar for Microsoft Office, Do Not Forward button to Microsoft Outlook, option in Windows File Explorer to classify and protect files, and PowerShell modules that can be used to bulk classify and protect files.  In a future post in this series I’ll be doing a deep dive of the client behavior including analysis of its calls to the Azure Information Protection endpoints via Fiddler.

    Unlike the AD RMS client of the past, the Azure Information Protection Client is supported on mobile operating systems such as iOS and Android.  Additionally, it supports a wider variety of file types than the AD RMS client supported.

  • Azure RMS-Integrated Server Applications

    Like its predecessor Azure RMS can be consumed by server applications such as Microsoft Exchange Server and Microsoft SharePoint Server with the RMS Connector.  There is native integration with Office 365 products including Exchange Online, SharePoint Online, OneDrive for Business, as well as being extensible to third-party applications via Cloud App Security (I’ll demonstrate this after I complete this series).  Like all good SaaS, there is also an API that can be leveraged to add the functionality to custom developed applications.

  • Rights Management Templates

    Azure RMS continues to use concepts of rights management templates like its predecessor.  Instead of being stored in a SQL database, the templates are stored in Microsoft’s cloud.  Templates created in AD RMS can also be imported into Azure RMS for continued use.  I’ll demonstrate how that process in a future post in this series.  Classification labels in AIP are backed by templates whenever a label applies protection with a pre-defined set of rights.  I’ll demonstrate this in a later post.

Far more simple in the SaaS world isn’t it?  In addition to simplicity Microsoft delivers more capabilities, tighter integration with its collaboration tools, and expansion of the capabilities to third party applies through a robust API and integration with Cloud App Security.

See you next post!

The Evolution of AD RMS to Azure Information Protection – Part 1

The Evolution of AD RMS to Azure Information Protection – Part 1

Collaboration.  It’s a term I hear at least a few times a day when speaking to my user base.  The ability to seamlessly collaborate with team members, across the organization, with trusted partners, and with customers is a must.  It’s a driving force between much of the evolution of software-as-a-service collaboration offerings such as Office 365.  While the industry is evolving to make collaboration easier than ever, it’s also introducing significant challenges for organizations to protect and control their data.

In a recent post I talked about Microsoft’s entry into the cloud access security broker (CASB) market with Cloud App Security (CAS) and its capability to provide auditing and alerting on activities performed in Amazon Web Services (AWS).  Microsoft refers to this collection of features as the Investigate capability of CAS.  Before I cover an example of the Control features in action, I want to talk about the product that works behind the scenes to provide CAS with many of the Control features.

That product is Azure Information Protection (AIP) and it provides the capability to classify, label, and protect files and email.  The protection piece is provided by another Microsoft product, Azure Active Directory Rights Management Services (Azure RMS).  Beyond just encrypting a file or email, Azure RMS can control what a user can do with a file such as preventing a user from printing a document or forwarding an email.  The best part?  The protection goes with the data even when it leaves your security boundary.

For those of you that have read my blog you can see that I am a huge fanboy of the predecessor to Azure RMS, Active Directory Rights Management Services (AD RMS, previously Rights Management Service or RMS for you super nerds).  AD RMS has been a role available in Microsoft Windows Server since Windows Server 2003.  It was a product well ahead of its time that unfortunately never really caught on.  Given my love for AD RMS, I thought it would be really fun to do a series looking at how AIP has evolved from AD RMS.   It’s a dramatic shift from a rather unknown product to a product that provides capabilities that will be as standard and as necessary as Antivirus was to the on-premises world.

I built a pretty robust lab environment (two actually) such that I could demonstrate the different ways the solutions work as well as demonstrate what it looks to migrate from AD RMS to AIP.  Given the complexity of the lab environment,  I’m going to take this post to cover what I put together.

The layout looks like this:

 

1AIP1.png

On the modern end I have an Azure AD tenant with the custom domain assigned of geekintheweeds.com.  Attached to the tenant I have some Office 365 E5 and Enterprise Mobility + Security E5 trial licenses  For the legacy end I have two separate labs setup in Azure each within its own resource group.  Lab number one contains three virtual machines (VMs) that run a series of services included Active Directory Domain Services (AD DS), Active Directory Certificate Services (AD CS), AD RMS, and Microsoft SQL Server Express.  Lab number two contains four VMs that run the same set as services as Lab 1 in addition to Active Directory Federation Services (AD FS) and Azure Active Directory Connect (AADC).  The virtual network (vnet) within each resource group has been peered and both resource groups contain a virtual gateway which has been configured with a site-to-site virtual private network (VPN) back to my home Hyper-V environment.  In the Hyper V environment I have two workstations.

Lab 1 is my “legacy” environment and consists of servers running Windows 2008 R2 and Windows Server 2012 R2 (AD RMS hasn’t changed in any meaningful manner since 2008 R2) and a client running Windows 7 Pro running Office 2013.  The DNS namespace for its Active Directory forest is JOG.LOCAL.  Lab 2 is my “modern” environment and consists of servers running Windows Server 2016 and a Windows 10 client running Office 2016 .  It uses a DNS namespace of GEEKINTHEWEEDS.COM for its Active Directory forest and is synchronized with the Azure AD tenant I mentioned above.  AD FS provides SSO to Office 365 for Geek in The Weeds users.

For AD RMS configuration, both environments will initially use Cryptographic Mode 1 and will have a trusted user domain (TUD).  SQL Server Express will host the AD RMS database and I will store the cluster key locally within the database.  The use of a TUD will make the configuration a bit more interesting for reasons you’ll see in a future post.

Got all that?

In my next post I’ll cover how the architecture changes when migrating from AD RMS to Azure Information Protection.