Azure AD Connect: Your first step towards an Hybrid Windows Environment

In this, my latest and straightest, blog post! We’ll start setting up a Hybrid Active Directory lab environment starting with the whats, whys, hows, and whos (?) of the Active Directory Connect tool! 

Let's be honest with ourselves. On-premise set-ups aren't going away anytime soon and Hybrid is here to stay for the foreseeable future. I'm not going to argue why that's a good or bad thing (I will say, however, that Hybrid environments can cause major headaches for admins and consultants a like...) but I have never had a client with fewer than 200 Windows users that didn't use some sort of hybrid setup. 

There are many scenarios where credentials from on-premises Active Directory environments are synchronized with Azure Active Directory. Credentials from on-premises Active Directory environments are synchronized with Azure Active Directory in a variety of scenarios. In addition to single sign-on, such synchronization is used for the use of cloud resources in Microsoft Azure or Microsoft 365, as well as for the use of Microsoft Endpoint Manager. Microsoft's Azure AD Connect tool is used to perform synchronization. Install the tool on a network server, connect to Microsoft Azure, and then synchronize the data.

User accounts can be synchronized between on-premises Active Directory (on-premises) forests and Azure Active Directory using Azure AD Connect.

Password hashes can also be synchronized on demand so that Azure AD user accounts can be used to authenticate to Azure and Microsoft 365 resources. Users are not required to re-authenticate, but their credentials on the local machine are transferred to Azure.

<# ----- Skip this block if you don’t want to read my whining about an unexpected invoice

This can be dangerous if you’re an inattentive tinkerer like me! I once had a received an unexpected $200 invoice because I’d set up a Bastion host to my home network and forgot that there’s a difference between stopping a VM and decommissioning a VM… as well as cocking up the cost alert that I thought I’d set up which was supposed to cap my PayG subscription.

I managed to talk my way out of it I cried so much to Azure support that they showed mercy by waiving the fee (it probably helped that it was a few days before Christmas too 😅) but there is no guarantee that you will be as lucky! It is completely at their discretion!

The really dumb thing is that I actually have Microsoft Partner Network subscriptions with free Azure credit AND access to CDX tenants through work (shout out to the homies at  VENZO! 😉) so, there was really no need reason for me to use a PayG sub other than being too lazy to move the subscription over to my home tenant.

Oh well. Live and learn.  ------ #>


What do you need?

To use Azure AD Connect, you’ll (of course) need a subscription to Microsoft Azure.  An Azure AD instance is free to setup and use. You’ll need a credit card but don’t worry about being charged for anything unless you go out of your way to select additional services to activate. If you haven’t previously used your credit card before, then you might as well sign up for the free trial.

Buyer beware; Microsoft has clamped down on being able to sign-up for multiple free trials using the same credit card number so I suggest taking advantage of the free trial while you can to check out some of the other cool stuff Azure is capable of! Because once the trial is over, your subscription switches over to a Pay-as-you-Go model.

The methods we’ll be going over aren’t necessarily exclusive to homelab usages and definitely also apply to “real” grown up Windows environments - but that’s the term I’m using since I’ll be posting screenshots from a virtualized environment.

An Active Directory Domain Controller is also needed since… well, we’re connecting an on-premise solution to Azure and you can’t have an on-premise solution without some sort of controller for you domain.  For security reasons, the installation should never be done directly on a domain controller, but it is possible. And since this is a homelab for testing purposes, we’ll be blowing caution to the wind since hey we’re using throw-way stuff here, right?

As to accounts, you will need:

Xxx A Global Administrator Account for your Azure tenant.

Xxx A Enterprise Administrator account for your Active Directory Domain (if you are using Express Settings. More on that later).

Moving on; Azure AD Connect stores the data in a SQL database before synchronization. By default, SQL Server 2012 Express LocalDB is used here. Azure AD Connect requires a graphical user interface. Installation on a core server running Windows Server 2016/2019 is not possible.

If you don’t already have your Windows Server VM set up (or don’t know how), read my A Quick 'n Dirty Guide to Setting up a Windows Server Lab guide.


Setting it up

Azure AD Connect setup starts from the Azure portal. The menu item "Azure Active Directory" is available here. Below "Azure Active Directory" you will find "Azure AD Connect". Here you can can also download the MSI file that you need to install as well as see the domains that are already connected - but since this is a freshly created tenant, there are no domains. and.

Alternatively you can also download Azure ADConnect directly from the Microsoft Download Center.

Once you’ve downloader the installer.. well, you know what to do. After you’ve done what you know to do launch the AD Connector tool.

After you have confirmed the license terms, you can use the Express Settings page to select whether you want to use the wizard's default settings or customize the setup. Most of the time, the express settings are sufficient. You sign in to Azure AD after selecting the Express settings.

There are, of course, many reasons why you would choose not to use the Express settings. Reasons such as:

  • You have more than 100,000 objects in your on-premises Active Directory.
  • You have multiple forests.
  • You use (or plan to use) federation or pass-through authentication for user sign-in.
  • You do not have access to a Enterprise Administrator account.
  • And a few other reasons you can read more about here.

Enter your Azure AD credentials. Most of the time, the connection should be established without incident. For troubleshooting tips on connection issues, see the Troubleshoot: Azure AD connectivity page. If the connection is successful, the next step is to enter the on-premises Active Directory credentials. The wizard double-checks the successful connection here as well.

And now your Enterprise Administrator credentials:

The AD Connect wizard then checks to see if the UPN suffixes of the on-premises Active Directory forest also exists in Azure AD. If you want to ensure that users can sign in to Azure AD with their on-premises login to Active Directory without re-entering credentials, the suffixes they use should be present in both environments.

However, you can also continue without adding the UPN to your cloud tenant. For now, we’ll go without.

The wizard then checks whether to proceed with the setup. The individual actions are displayed in the window:

The installatlon continues to set our Azure AD Connect up.

Once the wizard is complete, our On-Premise/Active Directory users should appear in the Microsoft365 admin center. The On-Premise/Active Directory Users should display the users from the on-premises Active Directory. Below are several dummy users (plus an additional admin account) I made for purpose of demonstrating the (hopefully! 🤞) success sync.

All done! On-premise at least. 

Let’s see if those users can be found in in the cloud.

Looks like it!

Users also appear in the Azure web portal. The Azure Active Directory\Users\All Userspane shows the synchronized users. Azure AD Connect also displays the status of the sync and when the last sync took place.

Configuring Azure AD Connect

Azure AD Connect can be configured on the server where it was installed. To do this, select the menu item whose settings you want to change and then click "Next" The appropriate settings can then be adjusted. Of course, before you can make any changes, you must first log in to Microsoft Azure. The credentials of the account that logged on to the computer are used to login to Active Directory. The Azure AD Connect configuration can be exported to a JSON file via the menu item "View or export current configuration".

Congratulations! You know have a hybrid active directory between your On-Premise and Azure!

Well, I think that just about does it for this post. But in the future we’ll cover more stuff related to hybrid environments, like:

  • Adding the On-Premise UPN ( to Azure
  • Hybrid Active Directory Joined Devices (HAADJ)
  • Pass-through authentication sign-on
  • And more!

In the meanwhile, the best way to learn is by absolutely destroying homelabs and deliberately trying to break them as much as you can so you can learn how to build them up again. Because even though VM snapshots are a great fallback for when you get really stuck – out there in the real world (read: production environments and brownfields) you will very rarely get to just do a start-over.

Have fun!