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.

5AIP1.png

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).

5AIP2.png

After a minute or two the installation will complete successfully.

5AIP3.png

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.

5AIP4.png

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.

5AIP5.png

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.

5AIP6.png

5AIP7.png

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.

5AIP8.png

5AIP9

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.

5AIP10.png

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.

5AIP11.png

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.

5AIP12

5AIP13.png

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.

5AIP14.png

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

5AIP15.png

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.

5AIP16.png

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.

5AIP17.png

5AIP18.png

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?

5AIP19.png

 

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.

5AIP20.png

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

5AIP24

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.

5AIP21

5AIP22

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.

5AIP23.png

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.

5AIP25.png

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 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.

Deep Dive into Azure AD Domain Services – Part 3

Deep Dive into Azure AD Domain Services  – Part 3

Well folks, it’s time to wrap up this series on Azure Active Directory Domain Services (AAD DS).  In my first post I covered the basic configurations of the managed domain and in my second post took a look at how well Microsoft did in applying security best practices and complying with NIST standards.  In this post I’m going to briefly cover the LDAPS over the Internet capability, summarize some key findings, and list out some improvements I’d like to see made to the service.

One of the odd features Microsoft provides with the AAD DS service is the ability to expose the managed domain over LDAPS to the Internet.  I really am lost as to the use case that drove the feature.  LDAP is very much a legacy on-premises protocol that has no place being exposed to risks of the public Internet.  It’s the last thing that should the industry should be encouraging.  Just because you can, doesn’t mean you should.   Now let me step off the soap box and let’s take a look at the feature.

As I covered in my last post LDAPS is not natively enabled in the managed domain.  The feature must be configured and enabled through the Azure Portal.  The configuration consists of uploading the private key and certificate the service will use in the form of a PKCS12 file (*.PFX).  The certificate has a few requirements that are outlined in the instructions above.  After the certificate is validated, it takes about 10-15 minutes for the service to become available.  Beyond enabling the service within the VNet, you additionally have the option to expose the LDAPS endpoint to the Internet.

3aads1.png

Microsoft provides instructions on how to restrict access to the endpoint to trusted IPs via a network security group (NSG) because yeah, exposing an LDAP endpoint to the Internet is just a tad risky.  To lock it down you simply associate an NSG with the subnet AAD DS is serving.  Once that is done enable the service via the option in the image above and wait about 10 minutes.  After the service is up, register a external DNS record for the service that points to the IP address noted under the properties section of the AADS blade and you’re good to go.

For my testing purposes, I locked the external LDAPS endpoint down to the public IP address my Azure VM was SNATed to.  After that I created an entry in the host file of the VM that matched the external DNS name I gave the service (whyldap.geekintheweeds.com) to the public IP address of the LDAPS endpoint in order to bypass the split-brain DNS challenge.  Initiating a connection from LDP.EXE was a success.

3aads2.png

Now that we know the service is running, let’s check out what the protocol support and cipher suite looks like.

3aads3.png

Again we see the use of deprecated cipher suites. Here the risk is that much greater since a small mistake with an NSG could expose this endpoint directly to the Internet.  If you’re going to use this feature, please just don’t.  If you’re really determined to, don’t screw up your NSGs.

This series was probably one of the more enjoyable series I’ve done since I knew very little about the AAD DS offering. There were a few key takeaways that are worth sharing:

  • The more objects in the directory, the more expensive the service.
  • Users and groups can be created directly in managed domain after a new organizational unit is created.
  • Password and lockout policy is insanely loose to the point where I can create an account with a three character password (just need to meet complexity requirements) and accounts never lockout.  The policy cannot be changed.
  • RC4 encryption ciphers are enabled and cannot be disabled.
  • NTLMv1 is enabled and cannot be disabled.
  • The service does not support smart-card enforced users.  Yes, that includes both the users synchronized from Azure AD as well as any users you create directly in the managed domain.  If I had to guess, it’s probably due to the fact that you’re not a Domain Admin so hence you can’t add to the NTAuth certificate store.
  • LDAPS is not enabled by default.
  • Schema extensions are not supported.
  • Account-Based Kerberos Delegation is not supported.
  • If you are syncing identities to Azure AD, you’ll also need to synchronize your passwords.
  • The managed domain is very much “out of the box” defaults.
  • Microsoft creates a “god” account which is a permanent member of every privileged group in the forest
  • Recovery of deleted objects created directly in the managed domain is not possible.  The rights have not been delegated to the AADC Administrator.
  • The service does not allow for Active Directory trusts
  • SIDHistory attribute of users and groups sourced from Azure AD is populated with Primary Group from on-premises domain

My verdict on AAD DS is it’s not a very useful service in its current state.  Beyond small organizations, organizations that have very little to no requirements on legacy infrastructure, organizations that don’t have strong security requirements, and dev/qa purposes I don’t see much of a use for it right now.  It comes off as a service in its infancy that has a lot of room to grow and mature.  Microsoft has gone a bit too far in the standardization/simplicity direction and needs to shift a bit in the opposite direction by allowing for more customization, especially in regards to security.

I’d really like to see Microsoft introduce the capabilities below.   All of them should  exposed via the resource blade in the Azure Portal if at all possible.  It would provide a singular administration point (which seems to be the strategy given the move of Azure AD and Intune to the Azure Portal) and would allow Microsoft to control how the options are enabled in the managed domain.  This means no more administrators blowing up their Active Directory forest because they accidentally shut off all the supported cipher suites for Kerberos.

  • Expose Domain Controller Event Logs to Azure Portal/Graph API and add support for AAD DS Power BI Dashboards
  • Support for Active Directory trusts
  • Out of the box provide a Red Forest model (get rid of that “god” account)
  • Option to disable risky cipher suites for both Kerberos and LDAPS
  • Option to harden the password and lockout policy
  • Option to disable NTLMv1
  • Option to turn on LDAP Debug Logging
  • Option to direct Domain Controller event logs to a SIEM
  • Option to restore deleted users and groups that were created directly in the managed domain.  If you’re allow creation, you need to allow for restoration.
  • Removal of Internet-accessible LDAPS endpoint feature or at least somehow incorporate the NSG lockdown feature directly into the AAD DS blade.

While the service has a lot of room for improvement the direction of a managed Windows AD offering is spot on.  In the year 2018, there is no reason Windows AD shouldn’t be offered as a managed service.  The direction Microsoft has gone by sourcing the identities and credentials from Azure AD is especially creative.  It’s a solid step in the direction of creating a singular centralized identity service that provides both legacy and modern protocols.  I’ll be watching this service closely as Microsoft builds upon it for the next few months.

Thanks and see you next post!

Deep Dive into Azure AD Domain Services – Part 1

Deep Dive into Azure AD Domain Services  – Part 1

Hi everyone.  In this series of posts I’ll be doing a deep dive into Microsoft’s Azure AD Domain Services (AAD DS).  AAD DS is Microsoft’s managed Windows Active Directory service offered in Microsoft Azure Infrastructure-as-a-Service intended to compete with similar offerings such as Amazon Web Services’s (AWS) Microsoft Active Directory.  Microsoft’s solution differs from other offerings in that it sources its user and group information from Azure Active Directory versus an on-premises Windows Active Directory or LDAP.

Like its competitors Microsoft realizes there are still a lot of organizations out there who are still very much attached to legacy on-premises protocols such as NTLM, Kerberos, and LDAP.  Not every organization (unfortunately) is ready or able to evolve its applications to consume SAML, Open ID Connect, OAuth, and Rest-Based APIs (yes COTS vendors I’m talking to you and your continued reliance on LDAP authentication in the year 2018).  If the service has to be there, it makes sense to consume a managed service so staff can focus less on maintaining legacy technology like Windows Active Directory and focus more on a modern Identity-as-a-Service (IDaaS), Software-as-a-Service (SaaS), and Platform-as-a-Service (Paas) solutions.

Sounds great right?  Sure, but how does it work?  Microsoft’s documentation does a reasonable job giving the high level details of the service so I encourage you to read through it at some point.  I won’t be covering information included in that documentation unless I notice a discrepancy or an area that could use more detail.  Instead, I’m going to focus on the areas which I feel are important to understand if you’re going to attempt to consume the service in the same way you would a traditional on-premises Windows Active Directory.

With that introduction, let’s dig in.

The first thing I did was to install the Remote Server Administration Tools (RSAT) for Active Directory Domain Services and Group Policy Management tools.  I used these tools to explore some of the configuration choices Microsoft made in the managed service.  I also installed Microsoft Network Monitor 3.4 to review packet captures  captured using the netsh.

After the tools were installed I started a persistent network capture using netsh using an elevated command prompt.  This is an incredibly useful feature of Windows when you need to debug issues that occur prior or during user or system logon.  I’ve used this for years to troubleshoot a number of Windows Active Directory issues including slow logons and failed logons.  The only downfall of this is you’re forced into using Microsoft Network Monitor or Microsoft Message Analyzer to review the packet captures it creates.  While Microsoft Message Analyzer is a sleek tool, the resources required to run it effectively are typically a non-starter for a lab or traditional work laptop so I tend to use Network Monitor.

entry1pic1

After the packet capture was started I went through the standard process of joining the machine to the domain and rebooting the computer.  After reboot, I logged in an account in the AAD DC Administrators Azure Active Directory group, started an elevated command prompt as the VM’s local administrator and stopped the packet capture.  This provided me with a capture of the domain join, initial computer authentication, and initial user authentication.

entry1pic2

While I know you’re as eager to dig into the packet capture as I am, I’ll cover that in a future post.  Instead I decided to break out the RSAT tools and poke around at configuration choices an administrator would normally make when building out a Windows Active Directory domain.

Let’s first open the tool everyone who touches Windows Active Directory is familiar with, Active Directory Users and Computers (ADUC).  The data layout (with Advanced Features option on) for organizational units (OUs) and containers looks very similar to what we’re used to seeing with the exception of the AADC Computers, AADC Users, AADDSDomainAdmin OUs, and AADDSDomainConfig container.  I’ll get into these containers in a minute.

entry1pic3.png

If we right-click the domain node and go to properties we see that the domain and forest are running in Windows Server 2012 R2 domain and forest functional level with no trusts defined.  Examining the operating system tab of the two domain controllers in the Domain Controllers OU shows that both boxes run Windows Server 2012 R2.  Interesting that Microsoft chose not to use Windows Server 2016.

entry1pic4.png

Navigating to the Security tab and clicking the Advanced button shows that the AAD DC Administrator group has only been granted the Create Organizational Unit objects permission while the AAD DC Service Accounts group has been granted Replicating Directory Changes.  As you can see from these permissions the base of the directory tree is very locked down.

entry1pic5.png

Let me circle back to the OUs and Containers I talked about above.  The AADDC Computers and AADDC Users OUs are the default OUs Microsoft creates for you.  Newly joined machines are added to the AADDC Computers OU and users synchronized from the Azure AD tenant are placed in the AADDC Users OU.  As we saw from the permissions above, we could use an account in the AAD DC Administrators group to create additional OUs under the domain node to delegate control to another set of more restricted admins, for the purposes of controlling GPOs if security filtering doesn’t meet our requirements, or for creating additional service accounts or groups for the workloads we deploy in the environment.  The permissions within the default OUs are very limited.  In the AADDC Computer OU GPOs can be applied and computer objects can be added and removed.  In the AADC Users OU only GPOs can be applied which makes sense considering the user and group objects stored there are sourced from your authoritative Azure AD tenant.

The AADDSDomainAdmin OU contains a single security group named AADDS Service Administrators Group (pre-Windows 2000 name of AADDSDomAdmGroup).  The group contains a single member names dcaasadmin which is the renamed built-in Active Directory administrator account.  The group is nested into a number of highly privileged built-in Active Directory groups including Administrators, Domain Admins, Domain Users, Enterprise Admins, and Schema Admins.  I’m very uncomfortable with Microsoft’s choice to make a “god” group and even a “god” user of the built-in administrator.  This directly conflicts with security best practices for Active Directory which would see no account being a permanent member of these highly privileged groups or at the least divvying up the privileges among separate security principals.  I would have liked to see Microsoft leverage a Red Forest Red Forest  design here.  Hopefully we’ll see some improvements as the service matures.  I’m unsure as to the purpose of the OU and this group at this time.

entry1pic6

The AADDSDomainConfig container contains a single container object named SchemaUpdate.  I reviewed the attributes of both containers hoping to glean some idea of the purpose of the containers and the only thing I saw of notice was the revision attribute was set to 2.  Maybe Microsoft is tracking the schema of their standard managed domain image via this attribute?  In a future post in this series I’ll do a comparison of this managed domain’s schema with a fresh Windows Server 2012 R2 schema.

entry1pic7.png

Opening Active Directory Sites and Services shows that Microsoft has chosen to leave the domain with a single site.  This design choice makes sense given that a limitation of AAD DS is that it can only serve a single region.  If that limitation is ever lifted, Microsoft will need to revisit this choice and perhaps include a site for each region.   Expanding the Default-First-Site-Name site and the Servers node shows the two domain controllers Microsoft is using to provide the Windows Active Directory service to the VNet.

entry1pic8

So the layout is simple, what about the group policy objects (GPO)?  Opening up the Group Policy Management Console displays five GPOs which are included in every managed domain.

entry1pic9.png

The AADDC Users GPO is empty of settings while the AADC Computers GPO has a single Preference defined that adds the AAD DC Administrators group to the built-in Administrators group on any member servers added to the OU.  The Default Domain Controllers Policy (DDCP) GPO is your standard out of the box DDCP with nothing special set.  The Default Domain Policy (DDP) GPO on the other hand has a number of settings applied.  The password policy is interesting… I get that you have the option to source all the user accounts within your AAD DS domain from Azure AD, but Microsoft is still giving you the ability to create user accounts in the managed domain as I covered above which makes me uncomfortable with the default password policy.  Microsoft hasn’t delegated the ability to create Fine Grained Password Policies (FGPPs) either, which means you’re stuck with this very lax password policy.  Given the lack of technical enforcement, I’d recommend avoiding creating user accounts directly in the managed domain for any purpose until Microsoft delegates the ability to create FGPPs.  The remaining settings in the policy are standard out of the box DDP.

entry1pic10.png

The GPO named Event Log GPO is linked to the Domain Controllers OU and executes a startup script named EventLogRetentionPolicy.PS1.  Being the nosy geek I am, I dug through SYSVOL to find the script.  The script is very simple in that it sets each event log to overwrite events over 31 days old.  It then verifies the results and prints the results to the console.  Event logs are an interesting beast in AAD DS.  An account in the AAD DC Administrators group doesn’t have the right to connect to the Event Logs on the DCs remotely and I haven’t come across any options to view those logs.  I don’t see any mention of them in the Microsoft documentation, so my assumption is you don’t get access to them at this time.  I have to imagine this is a show stopper for some organizations considering the critical importance of Domain Controller logs.  If anyone knows how to access these logs, please let me know.  I’d like to see Microsoft incorporate an option to send the logs to a syslog agent via a configuration option in the Azure AD Domain Services blade in the Azure Portal.

I’m going to stop here today.  In my next post I’ll do some poking around by running a port scan against the managed domain controllers to see what network flows are open, enable LDAPS to see what the SSL/TLS landscape looks like, and examine authentication protocols and algorithms supported (NTLMv1,v2, Kerberos DES, etc).  Thanks for reading!

Integrating Azure AD and G-Suite – Automated Provisioning

Integrating Azure AD and G-Suite – Automated Provisioning

Today I’ll wrap up my series on Azure Active Directory’s (Azure AD) integration with Google’s G-Suite.  In my first entry I covered the single-sign on (SSO) integration and in my second and third posts I gave an overview of Google’s Cloud Platform (GCP) and demonstrated how to access a G-Suite domain’s resources through Google’s APIs.  In this post I’m going to cover how Microsoft provides automated provisioning of user, groups, and contacts .  If you haven’t read through my posts on Google’s API (part 1, part 2) take a read through so you’re more familiar with the concepts I’ll be covering throughout this post.

SSO using SAML or Open ID Connect is a common capability of most every cloud solutions these days.  While that solves the authentication problem, the provisioning of users, groups, and other identity-relates objects remains a challenge largely due to the lack of widely accepted standards (SCIM has a ways to go folks).  Vendors have a variety of workarounds including making LDAP calls back to a traditional on-premises directory (YUCK), supporting uploads of CSV files, or creating and updating identities in its local databases based upon the information contained in a SAML assertion or Open ID Connect id token.  A growing number of vendors are exposing these capabilities via a web-based API.  Google falls into this category and provides a robust selection of APIs to interact with its services from Gmail to resources within Google Cloud Platform, and yes even Google G-Suite.

If you’re a frequent user of Azure AD, you’ll have run into the automatic provisioning capabilities it brings to the table across a wide range of cloud services.  In a previous series I covered its provisioning capabilities with Amazon Web Services.  This is another use case where Microsoft leverages a third party’s robust API to simplify the identity management lifecycle.

In the SSO Quickstart Guide Microsoft provides for G-Suite it erroneously states:

“Google Apps supports auto provisioning, which is by default enabled. There is no action for you in this section. If a user doesn’t already exist in Google Apps Software, a new one is created when you attempt to access Google Apps Software.”

This simply isn’t true.  While auto provisioning via the API can be done, it is a feature you need to code to and isn’t enabled by default.  When you enable SSO to G-Suite and attempt to access it using an assertion containing the claim for a user that does not exist within a G-Suite domain you receive the error below.

google4int1

This establishes what we already knew in that identities representing our users attempting SSO to G-Suite need to be created before the users can authenticate.  Microsoft provides a Quickstart for auto provisioning into G-Suite.  The document does a good job telling you were to click and giving some basic advice but really lacks in the detail into what’s happening in the background and describing how it works.

Let’s take a deeper look shall we?

If you haven’t already, add the Google Apps application from the Azure AD Application Gallery.  Once the application is added navigate to the blade for the application and select the Provisioning page.  Switch the provisioning mode from manual to automatic.

google4int2.png

Right off the bat we see a big blue Authorize button which tells us that Microsoft is not using the service accounts pattern for accessing the Google API.  Google’s recommendation is to use the service account pattern when accessing project-based data rather than user specific data.  The argument can be made that G-Suite data doesn’t fall under project-based data and the service account credential doesn’t make sense.  Additionally using a service account would require granting the account domain-wide delegation for the G-Suite domain allowing the account to impersonate any user in the G-Suite domain.  Not really ideal, especially from an auditing perspective.

By using the Server-side Web Apps pattern a new user in G-Suite can be created and assigned as the “Azure AD account”. The downfall with of this means you’re stuck paying Google $10.00 a month for a non-human account. The price of good security practices I guess.

google4int3.png

Microsoft documentation states that the account must be granted the Super Admin role. I found this surprising since you’re effectively giving the account god rights to your G-Suite domain. It got me wondering what authorization scopes is Microsoft asking for? Let’s break out Fiddler and walk through the process that kicks off after clicking on the Authorization button.

A new window pops up from Google requesting me to authenticate. Here Azure AD, acting as the OAuth client, has made an authorization request and has sent me along with the request over to the Google which is acting as the authorization server to authenticate, consent to the access, and take the next step in the authorization flow.

google4int4

When I switch over to Fiddler I see a number of sessions have been captured.  Opening the WebForms window of the first session to accounts.google.com a number of parameters that were passed to Google.

google4int5

The first parameter gives us the three authorization scopes Azure AD is looking for.  The admin.directory.group and admin.directory.user are scopes are both related to the Google Directory API, which makes sense if it wants to manage users and groups.  The /m8/feeds scope grants it access to manage contacts via the Google Contacts API.  This is an older API that uses XML instead of JSON to exchange information and looks like it has been/is being replaced by the Google People API.

Management of contacts via this API is where the requirement for an account in the Super Admin role originates.  Google documentation states that management of domain shared contacts via the /m8/feeds API requires an administrator username and password for Google Apps.  I couldn’t find any privilege in G-Suite which could be added to a custom Admin role that mentioned contacts.  Given Google’s own documentation along the lack of an obvious privilege option, this may be a hard limitation of G-Suite.  Too bad too because there are options for both Users and Groups.  Either way, the request for this authorization scope drives the requirement for Super Admin for the account Azure AD will be using for delegated access.

The redirect_uri is the where Google sends the user after the authorization request is complete.  The response_type tells us Azure AD and Google are using the OAuth authorization code grant type flow.  The client_id is the unique identifier Google has assigned to Azure AD in whatever project Microsoft has it built in.  The approval_prompt setting of force tells Google to display the consent window and the data Azure AD wants to access.  Lastly, the access_type setting of offline allows Azure AD to access the APIs without the user being available to authenticate via a refresh token which will be issued along with the access token.  Let’s pay attention to that one once the consent screen pops up.

I plug in valid super user credentials to my G-Suite domain and authenticate and receive the warning below.  This indicates that Microsoft has been naughty and hasn’t had their application reviewed by Google.  This was made a requirement back in July of 2017… so yeah… Microsoft maybe get on that?

google4int6.png

To progress to the consent screen I hit the Advanced link in the lower left and opt to continue.  The consent window then pops up.

google4int7.png

Here I see that Microsoft has registered their application with a friendly name of azure.com.  I’m also shown the scopes that the application wants to access which jive with the authorization scopes we saw in Fiddler.  Remember that offline access Microsoft asked for?  See it mentioned anywhere in this consent page that I’m delegating this access to Microsoft perpetually as long as they ask for a refresh token?  This is one of my problems with OAuth and consent windows like this.  It’s entirely too vague as to how long I’m granting the application access to my data or to do things as me.  Expect to see this OAuth consent attacks continue to grow in in use moving forward.  Why worry about compromising the user’s credentials when I can display a vague consent window and have them grant me access directly to their data?  Totally safe.

Hopping back to the window, I click the Allow button and the consent window closes.  Looking back at Fiddler I see that I received back an authorization code and posted it back to the reply_uri designated in the original authorization request.

google4int8.png

Switching back to the browser window for the Azure Portal the screen updates and the Test Connection button becomes available.  Clicking the button initiates a quick check where Azure AD obtains an access token for the scopes it requires unseen to the user.  After the successful test I hit the Save button.

google4int9.png

Switching to the browser window for the Google Admin Portal let’s take a look at the data that’s been updated for the user I used to authorize Microsoft its access.  For that I select the user, go to the Security section and I now see that the Azure Active Directory service is authorized to the contacts, user, and group management scopes.

google4int10.png

Switching back to the browser window for the Azure Portal I see some additional options are now available.

google4int11.png

The mappings are really interesting and will look familiar to you if you’ve ever done anything with an identity management tool like Microsoft Identity Manager (MIM) or even Azure AD Sync.  The user mappings for example show which attributes in Azure AD are used to populate the attributes in G-Suite.

google4int12.png

The attributes that have the Delete button grayed out are required by Google in order to provision new user accounts in a G-Suite domain.  The options available for deletion are additional data beyond what is required that Microsoft can populate on user accounts it provisions into G-Suite.  Selecting the Show advanced options button, allow you to play with the schema Microsoft is using for G-Suite.   What I found interesting about this schema is it doesn’t match the resource representation Google provides for the API.  It would have been nice to match the two to make it more consumable, but they’re probably working off values used in the old Google Provisioning API or they don’t envision many people being nerdy enough to poke around the schema.

Next up I move toggle the provisioning status from Off to On and leave the Scope option set to sync only the assigned users and groups.

google4int13.png

I then hit the Save button to save the new settings and after a minute my initial synchronization is successful.  Now nothing was synchronized, but it shows the credentials correctly allowed Azure AD to hit my G-Suite domain over the appropriate APIs with the appropriate access.

google4int14.png

So an empty synchronization works, how about one with a user?  I created a new user named dutch.schaefer@geekintheweeds.com with only the required attributes of display name and user principal name populated, assigned the new user to the Google Apps application and give Azure AD a night to run another sync.  Earlier tonight I checked the provisioning summary and verified the sync grabbed the new user.

google4int15.png

Review of the audit logs for the Google Apps application shows that the new user was exported around 11PM EST last night.  If you’re curious the synch between Azure AD and G-Suite occurs about every 20 minutes.

google4int16.png

Notice that the FamilyName and GivenName attributes are set to a period.  I never set the first or last name attributes of the user in Azure AD, so both attributes are blank.  If we bounce back to the attribute mapping and look at the attributes for Google Apps, we see that FamilyName and GivenName are both required meaning Azure AD had to populate them with something.  Different schemas, different requirements.

google4int17

Switching over to the Google Admin Console I see that the new user was successfully provisioned into G-Suite.

google4int18.png

Pretty neat overall.  Let’s take a look at what we learned:

  • Azure AD supports single sign-on to G-Suite via SAML using a service provider-initiated flow where Azure AD acts as the identity provider and G-Suite acts as the service provider.
  • A user object with a login id matching the user’s login id in Azure Active Directory must be created in G-Suite before single sign-on will work.
  • Google provides a number of libraries for its API and the Google API Explorer should be used for experimentation with Google’s APIs.
  • Google’s Directory API is used by Azure AD to provision users and groups into a G-Suite domain.
  • Google’s Contacts API is used by Azure AD to provision contacts into a G-Suite domain.
  • A user holding the Super Admin role in the G-Suite domain must be used to authorize Azure AD to perform provisioning activities.  The Super Admin role is required due to the usage of the Google Contact API.
  • Azure AD’s authorization request includes offline access using refresh tokens to request additional access tokens to ensure the sync process can be run on a regular basis without requiring re-authorization.
  • Best practice is to dedicate a user account in your G-Suite domain to Azure AD.
  • Azure AD uses the Server-side Web pattern for accessing Google’s APIs.
  • The provisioning process will populate a period for any attribute that is required in G-Suite but does not have a value in the corresponding attribute in Azure AD.
  • The provisioning process runs a sync every 20 minutes.

Even though my coding is horrendous, I absolutely loved experimenting with the Google API.  It’s easy to realize why APIs are becoming so critical to a good solution.  With the increased usage of a wide variety of products in a business, being able to plug and play applications is a must.  The provisioning aspect Azure AD demonstrates here is a great example of the opportunities provided when critical functionality is exposed for programmatic access.

I hope you enjoyed the series, learned a bit more about both solutions, and got some insight into what’s going on behind the scenes.

 

Integrating Azure AD and G-Suite – Google API Integration Part 1

Integrating Azure AD and G-Suite – Google API Integration Part 1

Hi everyone,

Welcome to the second post in my series on the integration between Azure Active Directory (Azure AD) and Google’s G-Suite (formally named Google Apps).  In my first entry I covered the single sign-on (SSO) integration between the two solutions.  This included a brief walkthrough of the configuration and an explanation of how the SAML protocol is used by both solutions to accomplish the SSO user experience.  I encourage you to read through that post before you jump into this.

So we have single sign-on between Azure AD and G-Suite, but do we still need to provision the users and group into G-Suite?  Thanks to Google’s Directory Application Programming Interface (API) and Azure Active Directory’s (Azure AD) integration with it, we can get automatic provisioning into G-Suite .  Before I cover how that integration works, let’s take a deeper look at Google’s Cloud Platform (GCP) and its API.

Like many of the modern APIs out there today, Google’s API is web-based and robust. It was built on Google’s JavaScript Object Notation (JSON)-based API infrastructure and uses Open Authorization 2.0 (OAuth 2.0) to allow for delegated access to an entities resources stored in Google. It’s nice to see vendors like Microsoft and Google leveraging standard protocols for interaction with the APIs unlike some vendors… *cough* Amazon *cough*. Google provides software development kits (SDKs) and shared libraries for a variety of languages.

Let’s take a look at the API Explorer.  The API Explorer is a great way to play around with the API without the need to write any code and to get an idea of the inputs and outputs of specific API calls.  I’m first going to do something very basic and retrieve a listing of users in my G-Suite directory.  Once I access the API explorer I hit the All Versions menu item and select the Admin Directory API.

google1int1

On the next screen I navigate down to the directory.users.list method and select it.  On the screen that follows I’m provided with a variety of input fields.  The data I input into these fields will affect what data is returned to me from the API. I put the domain name associated with my G-Suite subscription and hit the Authorize and Execute button.  A new window pops up which allows me to configure which scope of access I want to grant the API Explorer.  I’m going to give it just the scope of https://www.googleapis.com/auth/admin.directory.user.readonly.

google1int2

I then hit the Authorize and Execute button and I’m prompted to authenticate to Google and delegate API Explorer to access data I have permission to access in my G-Suite description.   Here I plug in the username and password for a standard user who isn’t assigned to any G-Suite Admin Roles.

google1int3

After successfully authenticating, I’m then prompted for consent to delegate API Explorer to view the users configured in the user’s G-Suite directory.

google1int4

I hit the allow button, the request for delegated access is complete, and a listing of users within my G-Suite directory are returned in JSON format.

google1int5

Easy right?  How about we step it up a notch and create a new user.  For that operation I’ll be delegating access to API Explorer using an account which has been granted the G-Suite User Management Admin role.  I navigate back to the main list of methods and choose the directory.users.insert method.  I then plug in the required values and hit the Authorize and Execute button.  The scopes menu pops up and I choose the https://www.googleapis.com/auth/admin.directory.user scope to allow for provisioning of the user and then hit the Authorize and Execute button.  The request is made and a successful response is returned.

google1int6

Navigating back to G-Suite and looking at the listing of users shows the new user Marge Simpson as appearing as created.

google1int7

Now that we’ve seen some simple samples using API Explorer let’s talk a bit about how you go about registering an application to interact with Google’s API as well as covering some basic Google Cloud Platform (GCP) concepts.

First thing I’m going to do is navigate to Google’s Getting Started page and create a new project.  So what is a project?  This took a bit of reading on my part because my prior experience with GCP was non-existent.  Think of a Google Project like an Amazon Web Services (AWS) account or a Microsoft Azure Subscription.  It acts as a container for billing, reporting, and organization of GCP resources.  Projects can be associated with a Google Cloud Organization (similar to how multiple Azure subscriptions can be associated with a single Microsoft Azure Active Directory (Azure AD) tenant) which is a resource available for a G-Suite subscription or Google Cloud Identity resource.  The picture below shows the organization associated with my G-Suite subscription.

google1int8

Now that we have the concepts out of the way, let’s get back to the demo. Back at the Getting Started page, I click the Create a new project button and authenticate as the super admin for my G-Suite subscription. I’ll explain why I’m using a super admin later. On the next screen I name the project JOG-NET-CONSOLE and hit the next button.

google1int9

The next screen prompts me to provide a name which will be displayed to the user when the user is prompted for consent in the instance I decide to use an OAuth flow which requires user consent.

google1int10

Next up I’m prompted to specify what type of application I’m integrated with Google.  For this demonstration I’ll be creating a simple console app, so I’m going to choose Web Browser simply to move forward.  I plug in a random unique value and click Create.

google1int11

After creation is successful, I’m prompted to download the client configuration and provided with my Client ID and Client Secret. The configuration file is in JSON format that provides information about the client’s registration and information on authorization server (Google’s) OAuth endpoints. This file can be consumed directly by the Google API libraries when obtaining credentials if you’re going that route.

google1int12

For the demo application I’m building I’ll be using the service account scenario often used for server-to-server interactions. This scenario leverages the OAuth 2.0 Client Credentials Authorization Grant flow. No user consent is required for this scenario because the intention of the service account scenario is it to access its own data. Google also provides the capability for the service account to be delegated the right to impersonate users within a G-Suite subscription. I’ll be using that capability for this demonstration.

Back to the demo…

Now that my application is registered, I now need to generate credentials I can use for the service account scenario. For that I navigate to the Google API Console. After successfully authenticating, I’ll be brought to the dashboard for the application project I created in the previous steps. On this page I’ll click the Credentials menu item.

google1int13

The credentials screen displays the client IDs associated with the JOG-NET-CONSOLE project.  Here we see the client ID I received in the JSON file as well as a default one Google generated when I created the project.

google1int14

Next up I click the Create Credentials button and select the Service Account key option.  On the Create service account key page I provide a unique name for the service account of Jog Directory Access.

The Role drop down box relates to the new roles that were introduced with Google’s Cloud IAM.

You can think of Google’s Cloud IAM as Google’s version of Amazon Web Services (AWS) IAM  or Microsoft’s Azure Active Directory in how the instance is related to the project which is used to manage the GCP resources.  When a new service account is created a new security principal representing the non-human identity is created in the Google Cloud IAM instance backing the project.

Since my application won’t be interacting with GCP resources, I’ll choose the random role of Logs Viewer.  When I filled in the service account name the service account ID field was automatically populated for me with a value.  The service account ID is unique to the project and represents the security principal for the application.   I choose the option to download the private key as a PKCS12 file because I’ll be using the System.Security.Cryptography.X509Certificates namespace within my application later on.  Finally I click the create button and download the PKCS12 file.

google1int15

The new service account now shows in the credential page.

google1int16

 

Navigating to the IAM & Admin dashboard now shows the application as a security principal within the project.

google1int17

I now need to enable the APIs in my project that I want my applications to access.  For this I navigate to the API & Services dashboard and click the Enable APIs and Services link.

google1int23.png

On the next page I use “admin” as my search term, select the Admin SDK and click the Enable button.  The API is now enabled for applications within the project.

From here I navigate down to the Service accounts page and edit the newly created service account.

google1int19

At this point I’ve created a new project in GCP, created a service account that will represent the demo application, and have given that application the right to impersonate users in my G-Suite directory.  I now need to authorize the application to access the G-Suite’s data via Google’s API.  For that I switch over to the G-Suite Admin Console and authenticate as a super admin and access the Security dashboard.  From there I hit the Advanced Setting option and click the Manage API client access link.

google1int20

On the Manage API client access page I add a new entry using the client ID I pulled previously and granting the application access to the  https://www.googleapis.com/auth/admin.directory.user.readonly scope.  This allows the application to impersonate a user to pull a listing of users from the G-Suite directory.

google1int21

Whew, a lot of new concepts to digest in this entry so I’ll save the review of the application for the next entry.  Here’s a consumable diagram I put together showing the relationship between GCP Projects, G-Suite, and a GCP Organization.  The G-Suite domain acts as a link to the GCP projects.  The G-Suite users can setup GCP projects and have a stub identity (see my first entry LINK) provisioned in the project.  When an service account is created in a project and granted G-Suite Domain-wide Delegation, we use the Client ID associated with the service account to establish an identity for the app in the G-Suite domain which is associated with a scope of authorized access.

google1int22

In this post I covered some basic GCP concepts and saw that the concepts are very similar to both Microsoft and AWS.  I also covered the process to create a service account in GCP and how all the pieces come together to programmatic access to G-Suite resources.  In my next entry I’ll demo some simple .NET applications and walk through the code.

Have a great weekend and go Pats!

Integrating Azure AD and G-Suite – Single Sign-On

Integrating Azure AD and G-Suite – Single Sign-On

Hi everyone,

After working through the Azure Active Directory (AD) and Amazon Web Services (AWS) integration I thought it’d be fun to do the same thing with Google Apps.  Google provides a generic tutorial for single sign-on that is severely lacking in details.  Microsoft again provides a reasonable tutorial for integrating Azure AD and Google Apps for single sign-on.  Neither gives much detail about what goes on behind the scenes or provides the geeky details us technology folk love.  Where there is a lack of detail there is a blogging opportunity for Journey Of The Geek.

In my previous post I covered the benefits of introducing Azure AD as an Identity-as-a-Service (IDaaS) component to Software-as-a-Service (SaaS) integrations.  Read the post for full details but the short of it is the integration gives you value-added features such as multifactor authentication with Azure Multifactor Authentication (MFA), adaptive authentication with Azure AD Identity Protection, contextual authorization with Azure AD Conditional Access, and cloud access security broker (CASB) functionality through Cloud App Security.  Supplementing Google Apps with these additional capabilities improves visibility, security, and user experience.  Wins across the board, right?

I’m going to break the integration into a series of posts with the first focusing on single sign-on (SSO).  I’ll follow up with a post exploring the provisioning capabilities Azure AD introduces as well as playing around with Google’s API.  In a future post I’ll demonstrate what Cloud App Security can bring to the picture.

Let’s move ahead with the post, shall we?

The first thing I did was to add the Google Apps application to Azure AD through the Azure AD blade in the Azure Portal. Once the application was added successfully I navigated to the Single sign-on section of the configuration. Navigate to the SAML Signing Certification section and click the link to download the certificate. This is the certificate Azure AD will be using to sign the SAML assertions it generates for the SAML trust. Save this file because we’ll need it for the next step.

I next signed up for trial subscription of Google’s G Suite Business. This plan comes with a identity store, email, cloud storage, the Google productivity suite, and a variety of other tools and features. Sign up is straightforward so I won’t be covering it. After logging into the Google Admin Console as my newly minted administrator the main menu is displayed. From here I select the Security option.googlesso1

Once the Security page loads, I select the Set up single sign-on (SSO) menu to expand the option.  Google will be playing the role of the service provider, so I’ll be configuring the second section.  Check the box to choose to Setup SSO with third party identity provider.  Next up you’ll need to identify what your specific SAML2 endpoint is for your tenant.  The Microsoft article still references the endpoint used with the old login experience that was recently replaced.  You’ll instead want to use the endpoint https://login.microsoftonline.com/<tenantID>/saml2You’ll populate that endpoint for both the Sign-In and Sign-Out URLs.  I opted to choose the domain specific issuer option which sets the identifier Google identifies itself as in the SAML authentication request to include the domain name associated with the Google Apps account.  You would typically use this if you had multiple subscriptions of Google Apps using the same identity provider.  The final step is upload the certificate you downloaded from Azure AD.  At this point Google configured to redirect users accessing Google Apps (exempting the Admin Console) to Azure AD to authenticate.

googlesso2

Now that Google is configured, we need to finish the configuration on Azure AD’s end.  If you follow the Microsoft tutorial at this point you’re going to run into some issues.  In the previous step I opted to use a domain specific issuer, so I’ll need to set the identifier to google.com/a/geekintheweeds.com.  For the user identifier I’ll leave the default as the user’s user principal name since it will match the user’s identifier in Google.  I also remove the additional attributes Azure AD sends by default since Google will discard them anyway.  Once the settings are configured hit the Save button.

googlesso3

Now that both the IdP and SP have been created, it’s time to create a user in Google App to represent my user that will be coming from Azure AD.  I refer to this as a “stub user” as it is a record that represents my user who lives authoritatively in Azure Active Directory.    For that I switch back to the Google Admin console, click the User’s button, and click the button to create a new user.

googlesso4

Earlier I created a new user in Azure AD named Michael Walsh that has a login ID of michael.walsh@geekintheweeds.com. Since I’ll be passing the user’s user principal name (UPN) from Azure AD, I’ll need to set the user’s Google login name to match the user’s UPN.

googlesso5

I then hit the Create button and my new user is created.  You’ll need that Google assigns the user a temporary password.  Like many SaaS solutions Google maintains a credential associated with the user even when the user is configured to use SSO via SAML.  Our SP and IdP are configured and the stub user is created in Google, so we’re good to test it out.

googlesso6

I open up Edge and navigate to the Google Apps login page, type in my username, and click the Next button.

googlesso7

I’m then redirect to the Microsoft login page where I authenticate using my Azure AD credentials and hit the sign in button.

googlesso8

After successfully authenticating to Azure AD, I’m redirected back to Google and logged in to my newly created account.

googlesso9

So what happened in the background to make the magic happen?  Let’s take a look at a diagram and break down the Fiddler conversation.

googlesso10

The diagram above outlines the simple steps used to achieve the user experience.  First the user navigates to the Google login page (remember SP-initiated SSO), enters his or her username, and is sent back an authentication request seen below extracted from Fiddler with instructs to deliver it back to the Azure AD endpoint for our tenant.

googlesso11

googlesso12.png

The user then authenticates to Azure AD and receives back a SAML response with instructions to deliver it back to Google. The user’s browser posts the SAML assertion to the Google endpoint and the user is successfully authenticated to Google.

googlesso13.png

googlesso14.png

Simple right?  In comparison to the AWS integration from an SSO-perspective, this was much more straightforward.  Unlike the AWS integration, it is required to have a stub user for the user in Google Apps prior to using SSO.  This means there is some provisioning work to perform… or does it?  Azure AD’s integration again offers some degree of “provisioning”.  In my next post I’ll explore those capabilities and perform some simple actions inside Google’s API.

See you next post!