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.


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:

  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.


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!


AWS and Microsoft’s Cloud App Security

AWS and Microsoft’s Cloud App Security

It seems like it’s become a weekly occurrence to have sensitive data exposed due to poorly managed cloud services.  Due to Amazon’s large market share with Amazon Web Services (AWS) many of these instances involve publicly-accessible Simple Storage Service (S3) buckets.  In the last six months alone there were highly publicized incidents with FedEx and Verizon.  While the cloud can be empowering, it can also be very dangerous when there is a lack of governance, visibility, and acceptance of the different security mindset cloud requires.

Organizations that have been in operation for many years have grown to be very reliant on the network boundary acting as the primary security boundary.  As these organizations begin to move to a software defined data center model this traditional boundary quickly becomes less and less effective.  Unfortunately for these organizations this, in combination with a lack of sufficient understanding of cloud, gives rise to mistakes like sensitive data being exposed.

One way in which an organization can protect itself is to leverage technologies such as cloud access security brokers (cloud security gateways if you’re Forrester reader) to help monitor and control data as it moves travels between on-premises and the cloud.  If you’re unfamiliar with the concept of a CASB, I covered it in a previous entry and included a link to an article which provides a great overview.

Microsoft has its own CASB offering called Microsoft Cloud App Security (CAS).  It’s offered as part of Microsoft’s Enterprise Mobility and Security (EMS) E5/A5 subscription.  Over the past several months multiple connectors to third party software-as-a-service (SaaS) providers have been introduced, including one for AWS.  The capabilities with AWS are limited at this point to pulling administrative logs and user information but it shows promise.

As per usual, Microsoft provides an integration guide which is detailed in button pushing, but not so much in concepts and technical details as to what is happening behind the scenes.  Since the Azure AD and AWS blog series has attracted so many views, I thought it would be fun and informative to do an entry for how Cloud App Security can be used with AWS.

I’m not in the habit of re-creating documentation so I’ll be referencing the Microsoft integration guide throughout the post.

The first thing that needs doing is the creation of a security principal in AWS Identity and Access Management (AWS IAM) that will be used by your tenant’s instance of CAS to connect to resources in your AWS account.   The first four steps are straightforward but step 5 could a bit of an explanation.

awscas1.pngHere we’re creating a custom IAM policy for the security principal granting it a number of permissions within the AWS account.  IAM policies are sets of permissions which are attached to a human or non-human identity or AWS resource and are evaluated when a call to the resource is made.  In the traditional on-premises world, you can think of it as something somewhat similar to a set of NTFS file permissions.  When the policy pictured above is created the security principal is granted a set of permissions across all instances of CloudTrail, CloudWatch, and IAM within the account.

If you’re unfamiliar with AWS services, CloudTrail is a service which audits the API calls made to AWS resources.  Some of the information included in the events include the action taken, the resource the action was taken upon, the security principal that made the action, the date time, and source IP address of the security principal who performed the action.  The CloudWatch service allows for monitoring of metrics and optionally triggering events based upon metrics reaching specific thresholds.  The IAM service is AWS’s identity store for the cloud management layer.

Now that we have a basic understanding of the services, let’s look at the permissions Microsoft is requiring for CAS to do its thing.  The CloudTrail permissions of DescribeTrails, LookupEvents, and GetTrailStatus allow CAS to query for all trails enabled on an AWS account (CloudTrail is enabled by default on all AWS resources), lookup events in a trail, and get information about the trail such as start and stop logging times.  The CloudWatch permissions of Describe* and Get* are fancy ways of asking for  READ permissions on CloudWatch resources.  These permissions include describe-alarms-history, describe alarms, describe-alarms-for-metric, get-dashboard, and get-metric-statistics.  The IAM permissions are similar to what’s being asked for in CloudWatch, basically asking for full read.

Step number 11 instructs us to create a new CloudTrail trail.  AWS by default audits all events across all resources and stores them for 90 days.  Trails enable you to direct events captured by CloudTrail to an S3 bucket for archiving, analysis, and responding to events.


The trail created is consumed by CAS to read the information captured via CloudTrail.  The permissions requested above become a bit more clear now that we see CAS is requesting read access for all trails across an account for monitoring goodness.  I’m unclear as to why CAS is asking for read for CloudWatch alarms unless it has some integration in that it monitors and reports on alarms configured for an AWS account.  The IAM read permissions are required so it can pull user  information it can use for the User Groups capability.

After the security principal is created and a sample trail is setup, it’s time to configure the connector for CAS.  Steps 12 – 15 walk through the process.  When it is complete AWS now shows as a connected app.


After a few hours data will start to trickle in from AWS.  Navigating to the Users and Accounts section shows all of the accounts found in the IAM instance for my AWS account.  Envision this as your one stop shop for identifying all of the user accounts across your many cloud services.  A single pane of glass to identity across SaaS.


On the Activity Log I see all of the API activities captured by CloudTrail.  If I wanted to capture more audit information, I can enable CloudTrail for the relevant resource and point it to the trail I configured for CAS.  I haven’t tested what CAS does with multiple trails, but based upon the permissions we configured when we setup the security principal, it should technically be able to pull from any trail we create.


Since the CAS and AWS integration is limited to pulling logging information, lets walk through an example of how we could use the data.  Take an example where an organization has a policy that the AWS root user should not be used for administrative activities due to the level of access the account gets by default.  The organization creates AWS IAM users accounts for each of its administrators who administer the cloud management layer.  In this scenario we can create a new policy in CAS to detect and alert on instances where the AWS root user is used.

First we navigate to the Policies page under the Control section of CAS.


On the Policies page we’re going to choose to create a new policy settings in the image below.  We’ll designate this as a high severity privileged account alert.  We’re interested in knowing anytime the account is used so we choose the Single Activity option.


We’ll pretend we were smart users of CAS and let it collect data for a few weeks to get a sampling of the types of events which are captured and to give us some data to analyze.  We also went the extra mile and leveraged the ability of CAS to pull in user information from AWS IAM such that we can choose the appropriate users from the drop-down menus.

Since this is a demo and my AWS lab has a lot of activity by the root account we’re going to limit our alerts to the creation of new AWS IAM users.  To do that we set our filter to look for an Activity type equal to Create user.  Our main goal is to capture usage of the root account so we add another filter rule that searches for a User with the name equal to aws root user where it is the actor in an event.


Finally we configure the alert to send an email to the administrator when the event occurs.  The governance capabilities don’t come into play in this use case.


Next we jump back to AWS and create a new AWS IAM user named testuser1.  A few minutes after the user is created we see the event appearing in CloudTrail.


After a few minutes, CAS generates and alert and I receive an email seen in the image below.   I’m given information as to the activity, the app, the date and time it was performed, and the client’s IP address.


If I bounce back to CAS I see one new Alert.  Navigating to the alert I’m able to dismiss it, adjust the policy that generated it, or resolve it and add some notes to the resolution.


I also have the option to dig deeper to see some of the patterns of the user’s behavior or the pattern of the behaviors from a specific IP address as seen below.



All this information is great, but what can we do with it?  In this example, it delivers visibility into the administrative activities occurring at the AWS cloud management layer by centralizing the data into a single repository which I can then send other data such as O365 activity, Box, SalesForces, etc.  By centralizing the information I can begin doing some behavioral analytics to develop standard patterns of behavior of my user base.  Understanding standard behavior patterns is key to being ahead of the bad guys whether they be insiders or outsiders.  I can search for deviations from standard patterns to detect a threat before it becomes too widespread.  I can also be proactive about putting alerts and enforcement (available for other app connectors in CAS but not AWS at this time) to stop the behavior before the threat is realized.  If I supplemented this data with log information from my on-premises proxy via Cloud App Discovery, I get an even larger sampling improving the quality of the data as well as giving me insight into shadow IT.  Pulling those “shadow” cloud solutions into the light allow me to ensure the usage of the services complies with organizational policies and opens up the opportunity of reducing costs by eliminating redundant services.

Microsoft categorizes the capabilities that help realize these benefits as the Discover and Investigate capabilities of CAS. The solution also offers a growing number of enforcement mechanisms (Microsoft categorized these enforcement mechanisms as Control) which add a whole other layer of power behind the solution.  Due to the limited integration with AWS I can’t demo those capabilities with this post.  I’ll cover those in a future post.

I hope this post helped you better understand the value that CASB/CSGs like Microsoft’s Cloud App Security can bring to the table.  While the product is still very new and a bit sparse on support with 3rd party applications, the list is growing every day. I predict the capabilities provided by technology such as Microsoft’s Cloud App Security will be as standard to IT as a firewall in the years to come.  If you’re already in Office 365 you should be ensuring you integrate these capabilities into your arsenal to understand the value they can bring to your business.

Thanks and have a wonderful week!

Office 365 Group Naming Policies – Part 2

Office 365 Group Naming Policies – Part 2

Welcome back.


In my first post I covered some of the methods organizations use to enforce a naming standard for groups, such as Active Directory groups, that are used to authorize access to data.  I also covered the challenges that are introduced when a mechanism for enforcing the naming standard doesn’t exist or isn’t effective and how this problem is becoming more prevalent with the increase in consumption of software-as-a-service applications.

Office 365 Groups are a core foundational component of Office 365 helping to enable simple, fast, and efficient collaboration within an organization.  For an organization to take full advantage of this, its end users need to be empowered to spin up Office 365 groups for mail-based collaboration or create new Teams for real-time collaboration. To make this work, IT can’t get in the way of the business and needs to let the business spin up and down Office 365 Groups as it needs them.  Microsoft has introduced a number of solutions to help with this including group expiration, integration with Office 365 retention policies, and the feature I’ll cover today, naming policies.

The naming policy feature is still in private preview but today I’m going to show you how to test the feature in your own tenant.  As a point of reference, I’m using a set of trial O365 E5 and Azure AD Premium P2 licenses within the commercial offering of Office 365 for my testing.  I can’t speak to whether or not the instructions below will work for Office 365 GCC or Office 365 Government.

The first thing I needed to do was install the Azure AD Preview module.  To do this I had to first remove the existing Azure AD module I had installed on my system and then install the Azure AD Preview module as seen below.


Comparing the modules using a get-command shows that the preview module has the new cmdlets below.


The cmdlets we’re interested in for this demonstration are the used to create and manage a new Graph API resource type called a directorySetting. The resource type is used to configure settings within Azure Active Directory. The directorySetting resource types are created from a template of configuration settings called a directorySettingTemplate resource type. Running the cmdlet Get-AzureADDirectorySettingTemplate displays the available to build a custom directorySetting from.


After connection to Azure AD using the Connect-AzureAD cmdlet, I can take a look at the templates available. The template I’m interested in for this blog is the Group.Unified template because it contains the settings for the naming policy as seen below.


Now that I’ve identified the template I want to draw from for a new directorySetting, I’m going to create a variable named $template and assign the Group.Unified template to it.  Running a quick Get-Member on the newly assigned displays a method named CreateDirectorySetting.  I’ll use this method to create a new instance of a directorySetting resource type based off the template and assign it to a variable named $setting.


If I run a Get-Member on $setting I can see that I’ve created a new instance of the directorySetting resource type which has the settings inherited from the Group.Unified template with some of those settings being configured with default values.


You’ll want to pay attention to these default values because once the settings become active for the tenant and seem to override settings configured within the GUI.  For example, if you are denying users the ability to create new Office 365 groups via the configuration setting in the Azure Active Directory blade in the Azure Portal, leaving the EnableGroupCreation setting as true will override that.  I’m not sure that is the intended behavior, but hey this is still preview right?

The next step is to configure the PrefixSuffixNamingRequirement setting with the naming convention I want enforced across my tenant.  This Microsoft article does a good job explaining your options and the syntax.  I went with a simple naming convention of including the fixed string “JOG” along with the value from the user’s department attribute in Azure Active Directory followed by the string value the user chooses for the group name.


Checking the values property of the $setting shows that the PrefixSuffixNamingRequirement is now populated with the value I entered above.


Now that the settings has been configured I make it active by using the New-AzureADDirectorySetting cmdlet and including the $setting directory object as input.


I then log into the Office 365 portal as a standard user and navigate to Outlook Web App and attempt to create a new Office 365 group. All new groups are now created using the naming convention I defined and it’s displayed clearly to the end users.


Hopefully Microsoft will refine the documentation as the feature moves out of preview and into general availability.  I also think this is a simple and static setting that would make sense to configurable from the GUI.  I’d also like to see the settings configurable with the directorySetting resource type be in sync with any corresponding settings in the GUI to avoid confusion.

That’s all there is to it.  Overall it’s a very simple yet elegant solution that solves naming convention woes while giving the business freedom to collaborate without having to go through IT.  You can’t beat that.


Office 365 Groups Naming Policies – Part 1

Office 365 Groups Naming Policies – Part 1

Groups…  It’s a term every business user consuming technology has heard at some point in time.  Most users only experience groups when they’re unable to access a specific application or file and the coworker sitting next to them informs them they need to call IT and get added to the department group.  Those of us who work on the technology side of the fence are very familiar with the benefits groups bring to the table when controlling access to data.  We are also quite familiar with the challenges they can bring when managing them at scale.

Something as simple as a lack of an enforced naming convention can create serious pain for an organization if it relies heavily upon the naming convention to determine the function and owner of a group.  The pain bleeds through IT and into the business as workers struggle with long wait times for on-boarding new employees due to IT trying to determine which groups the users need to be in.  When it comes time to perform an access review, business owners may waste valuable time trying to determine if removing an employee from a specific group will impact that employee’s ability to fulfill their job responsibilities.

In the on-premises world organizations deal with the challenge of naming conventions in different ways.  Most rely upon first or second level help desk to create groups according to the organization’s naming standard.  This method introduces the risk of human error and presents challenges when the group information for a particular application is sourced from a variety of different identity backends which force the staff to learning multiple tools.  Others make use of identity management (IDM) systems that automate the creation of groups and enforce the naming convention.  This method is very effective but also very costly due to high costs in implementing and operating an IDM.  A very small minority of organizations have evolved to the point where the naming conventions are no longer important due to robust reporting systems and entitlement databases.

Very few organizations are able to successfully execute the third method, which leaves them with the first or second.  The introduction of the software-as-a-service (SaaS) has made the first and second methods of enforcing a naming convention much more complicated.  Using the first method of leveraging help desk staff to create the groups manually is no longer scalable and the second method of using a centralized IDM system is often limited by the vendor’s ability to write connectors to the wide variety of APIs in use across the thousands of SaaS vendors.  All is not lost, as it seems some vendors have begun to recognize the challenge this can introduce to their customers.

If your organization is a consumer of Office 365, you’ve more than likely begun to use Office 365 Groups.  Office 365 groups offer a variety of features not found in the traditional security/distribution group or shared mailbox.  Take a look at this link for a comparison chart that documents the features.  One important thing to note is Office 365 Groups can only be only created in Azure Active Directory (AAD).  You cannot synchronize an on-premises Active Directory Domain Services security or distribution group to AAD and convert it to an Office 365 Group.  This means you can’t leverage an existing solution for enforcing naming conventions unless that solution has a connector into Azure AD.  Given features Office 365 provide and that they are the construct used by Microsoft Teams, you may make the decision to allow your users to create Office 365 Groups on the fly in order to allow them to take full advantage of collaboration tools available in Office 365.  To quote Peter Venkman, “Human sacrifice, dogs and cats living together… mass hysteria!”.

Calm down my friend.  Microsoft has a solution coming in the pipeline that will solve your Office 365 Groups naming convention woes.  In my next post I’ll demonstrate the feature and walkthrough how to test the feature out while it is in preview.