The Evolution of AD RMS to Azure Information Protection – Part 7 – Deep Dive into cross Azure AD tenant consumption

Posted on May 9, 2018 by mattfeltonma

Each time I think I’ve covered what I want to for Azure Information Protection (AIP), I think of another fun topic to explore. In this post I’m going to look at how AIP can be used to share information with users that exist outside your tenant. We’ll be looking at the scenario where an organization has a requirement to share protected content with another organization that has an Office 365 tenant.

Due to my requirements to test access from a second tenant, I’m going to supplement the lab I’ve been using. I’m adding to the mix my second Azure AD tenant at journeyofthegeek.com. Specific configuration items to note are as follows:

The tenant’s custom domain of journeyofthegeek.com is an Azure AD (AAD)-managed domain.
I’ve created two users for testing. The first is named Homer Simpson (homer.simpson@journeyofthegeek.com) and the second is Bart Simpson (bart.simpson@journeyofthegeek.com).
Each user have been licensed with Office 365 E3 and Enterprise Mobility + Security E5 licenses.
Three mail-enabled security groups have been created. The groups are named The Simpsons (thesimpsons@journeyofthegeek.com), JOG Accounting (jogaccounting@journeyofthegeek.com), and JOG IT (jogit@journeyofthegeek.com).
Homer Simpson is a member of The Simpsons and JOG Accounting while Bart Simpson is a member of The Simpsons and JOG IT.
Two additional AIP policies have been created in addition to the Global policy. One policy is named JOG IT and one is named JOG Accounting.
The Global AIP policy has an additional label created named PII that enforces protection. The label is configured to detect at least one occurrence of a US social security number. The document is protection policy allows only members of the The Simpsons group to the role of viewer.
The JOG Accounting and JOG IT AIP policies have both been configured with an additional label of either JOG Accounting or JOG IT. A sublabel for each label has also been created which enforces protection and restricts members of the relevant departmental group to the role of viewer.
I’ve repurposed the GIWCLIENT2 machine and have created two local users named Bart Simpson and Homer Simpson.

Once I had my tenant configuration up and running, I initialized Homer Simpson on GIWCLIENT2. I already had the AIP Client installed on the machine, so upon first opening Microsoft Word, the same bootstrapping process I described in my previous post occurred for the MSIPC client and the AIP client. Notice that the document has had the Confidential \ All Employees label applied to the document automatically as was configured in the Global AIP policy. Notice also the Custom Permissions option which is presented to the user because I’ve enabled the appropriate setting in the relevant AIP policies.

I’ll be restricting access to the document by allowing users in the geekintheweeds.com organization to hold the Viewer role. The geekintheweeds.com domain is associated with my other Azure AD tenant that I have been using for the lab for this series of posts. First thing I do is change the classification label from Confidential \ All Employees to General. That label is a default label provided by Microsoft which has an RMS Template applied that restricts viewers to users within the tenant.

One interesting finding I discovered through my testing is that the user can go through the process of protecting with custom permissions using a label that has a pre-configured template and the AIP client won’t throw any errors, but the custom permissions won’t be applied. This makes perfect sense from a security perspective, but it would be nice to inform the user with an error or warning. I can see this creating unnecessary help desk calls with how it’s configured now.

When I attempt to change my classification label to General, I receive a prompt requiring me to justify the drop in classification. This is yet another setting I’ve configured in my Global AIP policy. This seems to be a standard feature in most data classification solutions from what I’ve observed in another major vendor.

After successfully classifying the document with the General label protection is removed from the document. At this point I can apply my custom permissions as seen below.

I repeated the process for another protected doc named jog_protected_for_Ash_Williams.docx with permissions restricted to ash.williams@geekintheweeds.com. I packaged both files into an email and sent them to Ash Williams who is a user in the Geek In The Weeds tenant. Keep in mind the users in the Geek In The Weeds tenant are synchronized from a Windows Active Directory domain and use federated authentication.

After opening Outlook the message email from Homer Simpson arrives in Ash William’s inbox. At this point I copied the files to my desktop, closed Outlook, opened Microsoft Word and used the “Reset Settings” options of the AIP client, and signed out of my Office profile.

At this point I started Fiddler and opened one of the Microsoft Word document. Microsoft Word pops-up a login prompt where I type in my username of ash.williams@geekintheweeds.com and I’m authenticated to Office 365 through the standard federated authentication flow. The document then pops open.

Examining the Fiddler capture we see a lot of chatter. Let’s take a look at this in chunks, first addressing the initial calls to the AIP endpoint.

If you have previous experience with the MSIPC client in the AD RMS world you’ll recall that it makes its calls in the following order:

Searches HKLM registry hive
Searches HKCU registry hive
Web request to the RMS licensing pipeline for the RMS endpoint listed in the metadata attached to the protected document

In my previous deep dives into AD RMS we observed this behavior in action. In the AIP world, it looks like the MSIPC client performs similarly. The endpoint we see it first contacting is the Journey of the Geek which starts with 196d8e.

The client first sends an unauthenticated HTTP GET to the Server endpoint in the licensing pipeline. The response the server gives is a list of available SOAP functions which include GetLicensorCertificate and GetServerInfo as seen below.

The client follows up the actions below:

Now that the client knows the endpoint supports the GetServerInfo SOAP function, it sends an unauthenticated HTTP POST which includes the SOAP action of GetServerInfo. The AIP endpoint returns a response which includes the capabilities of the AIP service and the relevant endpoints for certification and the like.
It uses that information received from the previous request to send an unauthenticated HTTP POST which includes the SOAP action of ServiceDiscoveryForUser. The service returns a 401.

At this point the client needs to obtain a bearer access token to proceed. This process is actually pretty interesting and warrants a closer look.

Let’s step through the conversation:

We first see a connection opened to odc.officeapps.live.com and an unauthenticated HTTP GET to the /odc/emailhrd/getfederationprovider URI with query strings of geekintheweeds.com. This is a home realm discovery process trying to the provider for the user’s email domain.
My guess is this is MSAL In action and is allowing support for multiple IdPs like Azure AD, Microsoft Live, Google, and the like. I’ll be testing this theory in a later post where I test consumption by a Google user.

The server responds with a number of headers containing information about the token endpoints for Azure AD (since this is domain associated with an Azure AD tenant.)
A connection is then opened to odc.officeapps.live.com and an unauthenticated HTTP GET to the /odc/emailhrd/getidp with the email address for my user ash.williams@geekintheweeds.com. The response is interesting in that I would have thought it would return the user’s tenant ID. Instead it returns a JSON response of OrgId.

Since I’m a nosey geek, I decided to unlock the session for editing. First I put in the email address associated with a Microsoft Live. Instead of OrgId it returned MSA which indicates it detects it as being a Microsoft Live account. I then plugged in a @gmail.com account to see if I would get back Google but instead I received back neither. OrgId seems to indicate that it’s an account associated with an Azure AD tenant. Maybe it would perform alternative steps depending on whether it’s MSA or Azure AD in future steps? No clue.
Next, a connection is made to oauth2 endpoint for the journeyofthegeek.com tenant. The machine makes an unathenticated requests an access token for the https://api.aadrm.com/ in order to impersonate Ash Williams. Now if you know your OAuth, you know the user needs to authenticate and approve the access before the access token can be issued. The response from the oauth2 endpoint is a redirect over to the AD FS server so the user can authenticate.
After the user successfully authenticates, he is returned a security token and redirected back to login.microsoftonline.com where the assertion is posted and the user is successfully authenticated and is returned an authorization code.
The machine then takes that authorization code and posts it to the oauth2 endpoint for my journeyofthegeek.com tenant. It receives back an Open ID Connect id token for ash.williams, a bearer access token, and a refresh token for the Azure RMS API.

Decoding the bearer access token we come across some interesting information. We can see the audience for the token is the Azure RMS API, the issuer of the token is the tenant id associated with journeyofthegeek.com (interesting right?), and the identity provider for the user is the tenant id for geekintheweeds.com.
After the access token is obtained the machine closes out the session with login.microsoftonline.com and of course dumps a bunch of telemetry (can you see the trend here?).
A connection is again made to odc.officeapps.live.com and the /odc/emailhrd/getfederationprovider URI with an unauthenticated request which includes a query string of geekintheweeds.com. The same process as before takes place.

Exhausted yet? Well it’s about to get even more interesting if you’re an RMS nerd like myself.

Let’s talk through the sessions above.

A connection is opened to the geekintheweeds.com /wmcs/certification/server.asmx AIP endpoint with an unauthenticated HTTP POST and a SOAP action of GetServerInfo. The endpoint responds as we’ve observed previously with information about the AIP instance including features and endpoints for the various pipelines.
A connection is opened to the geekintheweeds.com /wmcs/oauth2/servicediscovery/servicediscovery.asmx AIP endpoint with an unauthenticated HTTP POST and a SOAP action of ServiceDiscoveryForUser. We know from the bootstrapping process I covered in my last post, that this action requires authentication, so we see the service return a 401.
A connection is opened to the geekintheweeds.com /wmcs/oauth2/certification/server.asmx AIP endpoint with an unauthenticated HTTP POST and SOAP action of GetLicensorCertificate. The SLC and its chain is returned to the machine in the response.
A connection is opened to the geekintheweeds.com /wmcs/oauth2/certification/certification.asmx AIP endpoint with an unauthenticated HTTP POST and SOAP action of Certify. Again, we remember from my last post that this requires authentication, so the service again responds with a 401.

What we learned from the above is the bearer access token the client obtained earlier isn’t attended for the geekintheweeds.com AIP endpoint because we never see it used. So how will the machine complete its bootstrap process? Well let’s see.

A connection is opened to the journeyofthegeek.com /wmcs/oauth2/servicediscovery/servicediscovery.asmx AIP endpoint with an unauthenticated HTTP POST and SOAP action of ServiceDiscoveryForUser. The service returns a 401 after which the client makes the same connection and HTTP POST again, but this time including its bearer access token it retrieved earlier. The service provides a response with the relevant pipelines for the journeyofthegeek.com AIP instance.
A connection is opened to the journeyofthegeek.com /wmcs/oauth2/certification/server.asmx AIP endpoint with an authenticated (bearer access token) HTTP POST and SOAP action of GetLicensorCertificate. The service returns the SLC and its chain.
A connection is opened to the journeyofthegeek.com /wmcs/oauth2/certification/certification.asmx AIP endpoint with an authenticated (bearer access token) HTTP POST and SOAP action of Certify. The service returns a RAC for the ash.williams@geekintheweeds.com along with relevant SLC and chain. Wait what? A RAC from the journeyofthegeek.com AIP instance for a user in geekintheweeds.com? Well folks this is supported through RMS’s support for federation. Since all Azure AD’s in a given offering (commercial, gov, etc) come pre-federated, this use case is supported.
A connection is opened to the journeyofthegeek.com /wmcs/licensing/server.asmx AIP endpoint with an uauthenticated HTTP POST and SOAP action of GetServerInfo. We’ve covered this enough to know what’s returned.
A connection is opened to the journeyofthegeek.com /wmcs/licensing/publish.asmx AIP endpoint with an authenticated (bearer access token) HTTP POST and SOAP action of GetClientLicensorandUserCertificates. The server returns the CLC and EUL to the user.

After this our protected document opens in Microsoft Word.

Pretty neat right? Smart move by Microsoft to take advantage and build upon of the federated capabilities built into AD RMS. This is another example showing just how far ahead of their game the product team for AD RMS was. Heck, there are SaaS vendors that still don’t support SAML, let alone on-premises products from 10 years ago.

In the next few posts (can you tell I find RMS fascinating yet?) of this series I’ll explore how Microsoft has integrated AIP into OneDrive, SharePoint Online, and Exchange Online.

Have a great week!

The Evolution of AD RMS to Azure Information Protection – Part 6 – Deep Dive into Client Bootstrapping

Posted on May 1, 2018 by mattfeltonma

Today I’m back with more Azure Information Protection (AIP) goodness. Over the past five posts I’ve covered the use cases, concepts and migration paths. Today I’m going to get really nerdy and take a look behind the curtains at how the MSIPC client shipped with Office 2016 interacts with AIP . I’ll be examining the MSIPC client log and reviewing procmon and Fiddler captures. If the thought of examining log files and SOAP calls excites you, this is a post for you. Make sure to take a read through my previous posts to ensure you understand my lab infrastructure and configuration as well as key AIP concepts.

Baselining the Client

Like any good engineer, I wanted to baseline my machine to ensure the MSIPC client was functioning correctly. Recall that my clients are migrating from an on-premises AD RMS implementation to AIP. I haven’t completed my removal of AD RMS so the service connection point for on-premises AD RMS is still there and the migration scripts Microsoft provides are still in use. Let’s take a look at the registry entries that are set via the Migrate-Client and Migrate-User script. In my last post I covered the purpose of the two scripts. For the purposes of this post, I’m going to keep it brief and only cover registry entries applicable to the MSIPC client shipped with Office 2016.

Migrate-Client
- Condition: Runs each computer startup only if it detects it has not run before or the version variable in the script has been changed.
- Registry Entries Modified:
  - Deletes HKLM\Software\Microsoft\MSIPC\ServiceLocation keys
  - Deletes HKLM\Software\Wow6432Node\Microsoft\MSIPC\ServiceLocation key
  - Deletes HKLM\Software\Microsoft\MSIPC\ServiceLocation\LicensingRedirection key
  - Deletes HKLM\Software\Wow6432Node\Microsoft\MSIPC\ServiceLocation\LicensingRedirection key
  - Add Default value to HKLM\Software\Microsoft\MSIPC\ServiceLocation\EnterpriseCertification key with data value pointing to AIP endpoint for tenant
  - Add Default value to HKLM\Software\Wow6432Node\Microsoft\MSIPC\ServiceLocation\EnterpriseCertification key with data value pointing to AIP endpoint for tenant
  - Add a value for the FQDN and single label URLs to on-premises AD RMS licensing pipeline to HKLM\Software\Microsoft\MSIPC\ServiceLocation\LicensingRedirection key with data values pointing to AIP endpoints for tenant
  - Add a value for the FQDN and single label URLs to on-premises AD RMS licensing pipeline to HKLM\Software\Wow6432NodeMicrosoft\MSIPC\ServiceLocation\LicensingRedirection key with data values pointing to AIP endpoints for tenant
Migrate-User
- Condition: Runs each user logon only if it detects it has not run before or the version variable in the script has been changed.
- Registry Entries Modified:
  - Deletes HKCU\Software\Microsoft\Office\16.0\Common\DRM key
  - Deletes HKCU\Software\Classes\Local Settings\Software\Microsoft\MSIPC key
  - Deletes HKCU\Software\Classes\Microsoft.IPViewerChildMenu\shell key
  - Add DefaultServerUrl value to HKCU\Software\Microsoft\Office\16.0\Common\DRM key and set its data value to the AIP endpoint for the tenant
- Files Modified:
  - Deletes the contents of the %localappdata%\Microsoft\MSIPC folder

A quick review of my client settings validates that all the necessary registry entries are in place and I have no issues consuming and created protected content.

Resetting the Client

If you have administered AD RMS in the past, you will be very familiar with how to re-bootstrap an RMS client. Microsoft has made that entire process easier by incorporating a “reset” function into the AIP client. The function can be accessed in Microsoft Office by hitting the drop down arrow for the AIP icon on the toolbar and selecting the Help and Feedback option.

After clicking the Help and Feedback option, a new window pops up where you can select the Reset Settings option to which performs a series of changes to the registry, deletions of RMS licenses, and AIP metadata. Lastly, I log out of the machine.

Bootstrapping the Client with Azure Information Protection

After logging back in I start up Fiddler, open Microsoft Word, and attempt to open a file that was protected with my AD RMS cluster. The file opens successfully.

One thing to note is if you’re using Windows 10 and Microsoft Edge like I was, you’ll need to take the extra steps outlined here to successfully capture due to the AppContainer Isolation feature added back in Windows 8. If you do not take those extra steps, you’ll get really odd behavior. Microsoft Edge will fail any calls to intranet endpoints (such as AD FS in my case) by saying it can’t contact the proxy. Trying with Internet Explorer will simply cause Fiddler to fail to make the calls and to throw a DNS error. Suffice to say, I spent about 20 minutes troubleshooting the issue before I remembered Fiddler’s dialog box that pops up every new install about AppContainer and Microsoft Edge.

The first thing we’re going to look at is the MSIPC log files which keep track of the client activity. I have to give an applause to whichever engineer over at Microsoft thought it would be helpful to include such a detailed log. If you’ve administered on-premises AD RMS in the past on previous versions of Microsoft Office, you’ll know the joys (pain?) of client side tracing with DebugView.

When we pop open the log we get some great detail as to the client behavior. We can see the client read a number of registry entries. The first thing we see is the client discover that is not initialized so it calls an API to bootstrap the user. Notice in the below that it has identified my user and it’s mentioning OAuth as a method for authentication to the endpoint.

Following this we have a few more registry queries to discover the version of the operating system. We then have our first HTTP session opened by the client. I’m pretty sure this session is the initial user authentication to Azure AD in order to obtain a bearer access token for the user to call further APIs

Bouncing over to Fiddler we can check out the authentication process. We can see the machine reach out to Azure AD (login.windows.net), perform home realm discovery which Azure AD determines that geekintheweeds.com is configured for federated authentication. The client makes the connection to the AD FS server where the user is seamlessly authenticated via Kerberos. The windowstransport endpoint is called which supports the WS-Trust 1.3 active profile. In an WS-Trust active flow, the client initiates the request (hence it’s active) vs the passive flow where the service provider initiates the flow. This is how Office applications support modern (aka federated) authentication.

After the assertion is obtained, it’s posted to the /common/oauth2/token endpoint at login.windows.net. The assertion is posted within a request for an access token, refresh token, and id token request using the saml1_1-bearer token grant type for the Azure RMS endpoint.

The machine is returned an access token, refresh token, and id token. We can see the token returned is a bearer token allowing client to impersonate my user moving forward.

Dumping the access token into the Fiddler TextWizard and decoding the Base64 gives us the details of the token. Within the token we can see an arm (authenticated method reference) of wia indicating the user authenticated using Windows authentication. A variety of information about the user is included in the token including UPN, first name, and last name.

I’m fairly certain the tokens are cached to a flat file based upon some of the data I did via procmon while the bootstrap process initiated. You can see the calls to create the file and write to it below.

After the tokens are obtained and cached we see from the log file that the MSIPC client then discovers it doesn’t have machine certificates. It goes through the process of creating the machine certificates.

We now see the MISPC client attempts to query for the SRV record Microsoft introduced with Office 2016 to help with migrations from AD RMS. The client then attempts discovery of service by querying the RMS-specific registry keys in the HKLM hive and comes across the information we hardcoded into the machine via the migration scripts. It uses this information to make a request to the non-authenticated endpoint of https://<tenant_specific>/_wmcs/certification/server.asmx.

Bouncing back to Fiddler and continuing the conversation we can see a few different connections are created. We see one to api.informationprotection.azure.com, another to mobile.pipe.aria.microsoft.com, and yet another to the AIP endpoint for my tenant.

I expected the conversation between api.informationprotection.azure.com and the AIP endpoint for my tenant. The connection to mobile.pipe.aria.microsoft.com interested me. I’m not sure if it was randomly captured or if it was part of the consumption of protected content. I found a few Reddit posts where people were theorizing it has something to do with how Microsoft consumes telemetry from Microsoft Office. As you could probably guess, this piqued my interest to know what exactly Microsoft was collecting.

We can see from the Fiddler captures that an application on the client machine is posting data to https://mobile.pipe.aria.microsoft.com/Collector/3.0/. Examination of the request header shows the user agent as AriaSDK Client and the sdk-version of ACT-Windows Desktop. This looks to be the method in which the telemetry agent for Office collects its information.

If we decode the data within Fiddler and dump both sets of data to Notepad we get some insight into what’s being pulled. Most of the data is pretty generic in that there is information about the version of Word I’m using, the operating system version, information that my machine is a virtual machine, and some activity IDs which must relate to something MS holds on their end. The only data point I found interesting was that my tenant ID is included in it. Given tenant id isn’t exactly a secret, it’s still interesting it’s being collected. It must be fascinating to see this telemetry at scale. Interesting stuff either way.

Continuing the conversation, let’s examine the chatter with my tenant’s AIP endpoint since the discovery was requested by the MSIPC client. We see a SOAP request of GetServerInfo posted to https://<tenant_specific>/_wmcs/certification/server.asmx. The response we receive from the endpoint has all the information our RMS client will need to process the request. My deep dive into AD RMS was before I got my feet with Fiddler so I’ve never examined the conversations with the SOAP endpoints within AD RMS. Future blog post maybe? Either way, I’ve highlighted the interesting informational points below. We can see that the service is identifying itself as RMS Online, has a set of features that cater to modern authentication, runs in Cryptomode 2, and supports a variety of authentication methods. I’m unfamiliar with the authentication types beyond X509 and OAuth 2. Maybe carry overs from on-prem? Something to explore in the future. The data boxed in red are all the key endpoints the RMS client needs to know to interact with the service moving forward. Take note the request at this endpoint doesn’t require any authentication. That comes in later requests.

After the response is received the MSIPC writes a whole bunch of registry entries to the HKCU hive for the user to cache all the AIP endpoint information it discovered. It then performs a service discovery against the authenticated endpoint using its bearer token it cached to the tokencache file.

Once the information is written to the registry, the client initiates a method called GetCertAndLicURLsWithNewSD. It uses the information it discovered previously to query the protected endpoint https://<tenant_specific>/_wmcs/oauth2/servicediscovery/servicediscovery.asmx. Initially it receives a 401 unauthorized back with instructions to authenticate uses a bearer token.

The client tries again this time providing the bearer token it obtained earlier and placed in the tokencache file. The SOAP action of ServiceDiscoveryForUser is performed and the client requests the specific endpoints for certification, licensing, and the new tracking portal feature of AIP.

The SOAP response contains the relevant service endpoints and user for which the query applied to.

The MSIPC client then makes a call to /_wmcs/oauth2/certification/server.asmx with a SOAP request of GetLicensorCertificate. I won’t break that one down response but it returns the SLC certificate chain in XrML format. For my tenant this included both the new SLC I generated when I migrated to AIP as well as the SLC from my on-premises AD RMS cluster that I uploaded.

The MISPC log now shows a method called GetNewRACandCLC being called which is used to obtain a RAC and CLC. This is done by making a call to the certification pipeline.

The call to /_wmcs/oauth2/certification/certification.asmx does exactly as you would expect and calls the SOAP request of Certify. This included my user’s RAC, and both SLCs and certificates in that chain. The one interesting piece in the response was a Quota tag as seen below. I received back five certificates, so maybe there is a maximum that can be returned? If you have more than 4 on-premises AD RMS clusters you’re consolidating to AIP, you might be in trouble. 🙂

The MISPC log captures the successful certification and logs information about the RAC.

Next up the client attempts to obtain a CLC by calling continuing with the GetNewRACandCLC method. It first calls the /_wmcs/licensing/server.asmx pipeline and makes a GetServerInfo SOAP request which returns the same information we saw in the last request to server.asmx. This request isn’t authenticated and the information returned is written to the HKCU hive for the user.

The service successfully returns the users CLC. The last step in the process is the MSIPC service requests the RMS templates associated with the user. You can see the template that is associated custom AIP classification label I created.

Last but not least, the certificates are written to the %LOCALAPPDATA%\Microsoft\MSIPC directory.

Conclusion

Very cool stuff right? I find it interesting in that the MSIPC client performs pretty much the same way it performs with on-premises exempting some of the additional capabilities introduced such as the search for the SRV DNS records and the ability to leverage modern authentication via the bearer token. The improved log is a welcome addition and again, stellar job to whatever engineer at Microsoft thought it would be helpful to include all the detail that is included in that log.

If you’ve used AD RMS or plan to use AIP and haven’t peeked behind the curtains I highly recommend it. Seeing how all the pieces fit together and how a relatively simple web service and a creative use of certificates can provide such a robust and powerful security capability will make your appreciate the service AD RMS tried to be and how far ahead of its time it was.

I know I didn’t cover the calls to the AIP-classification specific web calls, but I’ll explore that in my next entry. Hopefully you enjoyed nerding out on this post as much as I did. Have a great week and see you next post!

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

Posted on April 17, 2018 by mattfeltonma

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.

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).

After a minute or two the installation will complete successfully.

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.

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.

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.

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.

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.

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.

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.

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.

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

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:

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.
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.

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.

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?

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.

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

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.

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.

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.

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

Posted on April 8, 2018 by mattfeltonma

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.

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.

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.

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.

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.

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.

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

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.

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!

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Tag Archives: AD RMS

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