Field Notes: How has your Azure AD Connect been configured?

As a consultant, I see a lot of different environments. Often, I need to know the answer to one of the most important questions:

What did you select during the setup of Azure AD Connect?

The answers vary:

A colleague did the setup and has left the company, department…

A external supplier did the setup for a pilot or part of a project…

Of course, these answers are supported by a lack of documentation.

Why is this important to know?

During the setup of Azure AD Connect, the Microsoft Azure Active Directory Connect wizard shows several options. These options are only shown during the initial setup. Some of these options are not displayed when you perform the View Configuration task after initial configuration. Some options cannot be altered after the initial configuration; They can only be achieved with a new installation of Azure AD Connect, except for one option.

Initial setup options

Let’s look at these options as they are presented chronologically as you perform a Custom settings installation of Azure AD Connect:

Uniquely identifying your users
(cannot be altered after initial config)

When you install your first Azure AD Connect instance and configure the connection to Azure Active Directory, the following setup options are presented on the Uniquely identifying your users page of the Microsoft Azure Active Directory Connect wizard:

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The top half of the Uniquely identifying your users page shows the option to configure how Azure AD Connect should behave, when the organization has deployed a user account forest and resource forest Active Directory topology. However, a more common scenario is when an organization merges with another organization and is consolidating resources; Instead of two Exchange Server environments or Skype for Business Server environments, all is provisioned from one forest.

Custom installation - sourceAnchor configuration

The bottom half of the Uniquely identifying your users page allows the option to choose the source anchor.

The Microsoft documentation on these options can be found here.

Azure AD sign-in configuration
(cannot be altered after initial config)

The second option is the selection of the source for the Azure Active Directory UserPrincipalName on the Azure AD sign-in configuration page of the Microsoft Azure Active Directory Connect wizard.

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During the installation wizard, the administrator can choose which on-premises attribute should be used to populate the Azure Active Directory UserPrincipalName attribute.

The Microsoft documentation on this option can be found here.

Filter users and devices
(can be altered after initial config)

The last option I want to discuss is intended for pilot use only. The option on the Filter users and devices page enables administrators to  scope what objects are synchronized, based on a group membership instead of a selection of Organizational Units (OUs) and containers:image

The Microsoft documentation on this option can be found here.

What is configured in Azure AD Connect

Of course, we want to answer the initial question.

Native tooling

There are two ways to get the configuration from the Azure AD Connect server using native tooling:

  1. Azure AD Connect’s Graphical User Interfaces (GUIs)
  2. Windows PowerShell

The GUI provides almost all the information you need. However, if you have configured the “pilot” group filtering, you see it’s enabled, but you cannot see the actual configured group.  If you also want to see the group. Then you will need to go to the second option.

The second option is to use Windows PowerShell to get all the configured options for your Azure AD Connect configuration.

Third-party tooling

A third option is to use a third party tool called Azure AD Connect Configuration Documenter.

Using the Graphical User Interface

The steps below describe how to use the graphical user interface (GUI) to get information on the configured options:

  1. Sign in interactively to the Azure AD Connect server using an account that is a member of local Administrators and the SyncAdmins groups.
  2. Open the “Azure AD Connect ” link to the Microsoft Azure Active Directory Connect wizard, found on the desktop or start menu.
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  3. Click Configure on the Welcome to Azure AD Connect page:
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  4. Select the View current configuration task on the Additional tasks page and click Next.
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  5. All the configuration options are shown on the Review Your Solution page:
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So let’s review our configured solution:

The first part provides information on the Azure AD tenant, the  Active Directory environments it is connected to and the Azure AD Connect service account per Active Directory environment:
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The second part provides the actual configuration of the Azure AD Connect instance:
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The top two rows of this information shows the configured options that are mentioned before:

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In the table below I map the configuration item to the setup option.

Configuration Item Setup Option
SOURCE ANCHOR image
USER PRINCIPAL NAME image
SYNC CRITERIA image
FILTER OBJECTS TO SYNCHRONIZE BY GROUP image

As mentioned before, the GUI shows that we configured a group to scope synchronization, but it will not show the actual configured group:

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The Windows PowerShell steps below provides the method to get the actual group name

Using Windows PowerShell

The steps below describe how to use Windows PowerShell to get information on the configured options:

  1. Sign in interactively to the Azure AD Connect server using an account that is a member of local Administrators and the SyncAdmins groups.
  2. Open Windows PowerShell as administrator.
  3. Issue the following line of Windows PowerShell: Get-ADSyncGlobalSettingsParameter | Select-Object * | Sort-Object -Property Name | Out-GridView
  4. It will now show the configured options of Azure AD Connect:
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In the Out-GridView windows there are multiple entries. In the table below a overview of the configuration items and setup option is shown:

Configuration item Setup Option
Microsoft.OptionalFeature.GroupFiltering image
Microsoft.SynchronizationOption.AnchorAttribute image
Microsoft.SynchronizationOption.JoinCriteria image
Microsoft.SynchronizationOption.UPNAttribute image

To get the actual configured group that is configured on the Filter users and devices page, follow these steps:

  1. Issue the following line of Windows PowerShell in the elevated Windows PowerShell window:( (Get-ADSyncConnector).GlobalParameters | Where-Object {$_.Name -eq “Connector.GroupFilteringGroupDn”} ).Value
  2. It will now show the configured group:image

Using the Azure AD Connect Configuration Documenter

The Azure AD Connect Configuration Documenter is a free tool to document the configuration of Azure AD Connect. It is available on GitHub.

I use this tool every time when an update is needed of a Azure AD Connect instance. I use it to get a snapshot of the configuration before an update and after the update. Also, I use it to compare the configuration between Azure AD Connect instances, when an organization has one or more Azure AD Connect Staging Mode instances running or has instances running in their development, test, acceptance and production environments.

To use the tool, follow the provided instructions located in the readme file on GitHub.

The tool creates a report. In the report, there is a Global Settings section and this looks similar to the output when you’d use Windows PowerShell:

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At time of writing this blog. The Azure AD Connect Configuration Documenter doesn’t show the configured group on the Filter users and devices page, if the option to filter based on a group has been activated.

Concluding

For me, as a consultant, it’s important to provide as much documentation as possible to the customer about what I did or what is configured.

When I configure Azure AD Connect,  I use the Problem Step Recorder (PSR) a lot, which is available by default on Windows installations and installations of Windows Server with the Desktop Experience. PSR takes a full screenshot when you click your mouse and when you type and leave the entry field. The PSR file of my activities is the raw draft for the actual as-built documentation that I always deliver to my customers.

I hope every consultant and systems administrator uses the same method, but it’s not always the case. If not, I use the described methods to retrieve the actual Azure AD Connect configuration.

I hope to have given you the tools to retrieve the configuration yourselves, and find out what is actually configured, too.

Field notes: Azure AD Identity protection end-user perspective

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In my previous blog post Field Notes: Azure AD Identity Protection we looked at the administrator perspective on Identity Protection. The focus was how to protect your corporate accounts.
In this blog the focus is the end-user (employee and IT staff) experiences.

The experiences I want to share are:

  • Suspicious Activity
  • User with a high-risk classification
  • Behavior observed with Azure AD Password-less sign-in.

Employee experience

Suspicious Activity

When an employee uses a browser or modern authentication, this dialog will appear, when the conditions of a risky sign-in have been detected:

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Risky sign-ins are medium-risk events. Example triggers for events are:

  • Signing-in from two separate locations in the world with an impossible travel time. However, this can also be detected, when a corporate VPN is used and it forces all internet traffic through the tunnel. Another false positive might be detected when using remote systems in datacenters located in another location. Please note that ‘location’ in Identity Protection-speak is usually in the scale of a small country or US state.
    For example: 10:10 am sign-in from Amsterdam and on 10:15am a sign-in from Redmond, WA in the USA.
  • Using a VPN connection, proxy or browser to anonymize your real IP location. NordVPN and the Tor browser are great examples and we use them to demo Identity Protection detections effectively.
  • Connecting from a public IP address with a bad reputation, due to infected machines at that location. For example, connections from internet cafes and public hotspots.

Employee with a high-risk classification

When an employee meets the threshold of medium events or the situation score calculation algorithm generates a high score, the user will be blocked from access, by default.

The user feedback I received, is that the authenticator app gives an error message, and tells the end-user to contact the systems administrator. Microsoft Office Outlook will not connect on your machine.

The only way to know what is going on is to use a browser to sign into the Office 365 environment, for example.

Depending on your tenant’s Identity Protection configuration, an employee can validate and reset the password to his or her account or be blocked until an administrator forces a password reset for the affected user account.

Note: Microsoft has added the ability to do a self-service password reset via the Authenticator app. This paves the way for resolving high-risk events from within the Microsoft Authenticator app, if the policy allows end-user reset in a high risk situation.

Azure AD Password-less sign-in

If you have configured Password-less sign-in with Azure AD, the user experience is different, when it comes to risky sign-in sessions. The end-user will not be shown a prompt that the sign-in session is calculated to be risky. A mere alert will be generated in Azure AD Identity Protection and depending on the configuration, sent to the IT staff for notification. The event itself will be automatically closed, because multi-factor authentication is performed.

IT Staff experience

Out-of-the box alert

In all three cases above, Azure AD Identity Protection will generate an alert e-mail that a risky event has occurred. This alert is sent to the configured mail recipients. The message itself does not contain the actual account information or threat level. In order to consume this information, you need to sign-in the Azure AD Identity Protection portal.

The message the IT staff receive is shown below:

Graph API

If the security teams wants faster insights, they should leverage the Graph API and create an automation option to retrieve the Azure AD Identity Protection data. This option is documented here. An example output is shown below, using the PowerShell code provided in the Microsoft documentation:

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Using the Graph APU enables the IT/security staff to retrieve detailed information on security events, directly from the tenant. This enables  automation and faster insights into what is going on. An automation example is a query is formatted to a readable event for the organization’s SIEM solution or Log Analytics.

Processing a risk event

Azure AD Identity Protection has three levels of administrator access.

Role Able to do not able to do
Global Administrator Full access to Azure AD Identity Protection, Onboard Azure AD Identity Protection
Security Administrator Full access to Azure AD Identity Protection Onboard Azure AD Identity Protection, reset passwords for a user
Security Reader Read-only access to Azure AD Identity Protection Onboard Identity Protection, remediate users, configure policies, reset passwords

The minimum level IT staff personnel need to process the security events and give back control to the end users, is to be assigned the Security Administrator role to gain access to Azure AD Identity Protection. Additionally, they need the User Administrator or Password Administrator role to reset passwords for affected users for them to regain access to the company resources.

In a event of a blocked user, the IT admin has two choices after reviewing the security events first for the affected user.

  1. When the events are legitimate, they can force a reset of the user password and provide the end-user with the new temporary password.
  2. When event are false positives, they can mark them as such in the web portal, so Azure AD machine learning can learn from it and lower the security score of the end-user in the process.

A better approach

The information that Microsoft supplies in case of a high risk event is minimal for an end-user. He or she is not properly informed on what is going on and what steps to take.

From a service desk/IT staff perspective, the information alert mail doesn’t contain direct information. It is not directly useful to prioritize the event. To gather the actual information, the IT admin needs to login and lookup the event. This takes time. Depending on the workload, it may not always be visible straight away.

The combination of the above two experiences is that when an employee contacts the service desk, time is lost with troubleshooting, because the error is not properly shown from the end-user interface, unless when using a browser.

A solution here, would be an automation script that runs in the background and registers an incident in the ticket system and an event for SIEM, based on the employee information and give it a high priority. In addition to that, a separate e-mail can be sent to the security staff with more detail. Also a brief e-mail can be sent to the service desk to be informed that a user is blocked.

This way, service desk personnel can be properly informed and can even pro-actively contact the effected employees and guide them through the process.

Concluding

Don’t waste valuable time troubleshooting risky sign-ins and high-risk events that block employee sign-ins. Get the pro-active edge.

Field notes: Azure AD Identity Protection

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I’m managing several Azure AD tenants with a wide variety of licenses and settings. I’ve had a focus on Azure AD Identity Protection for the last weeks, so I’m sharing my field notes with you.

What is Azure AD Identity Protection?

Let’s start with a little introduction.

Microsoft has a lot of experience with identities in the cloud. These identities are used for public cloud features like onedrive.com and outlook.com, but also for the organizational cloud identities within Azure Active Directory.

With the presence of one or more Azure AD Premium 2 license(s) in the tenant, an organization can benefit from additional security options and automated actions to secure their organizational identities within that tenant. The global administrator account that is going to be used to activate the feature, should be enabled with a Azure AD Premium P2 license.

Azure AD Identity Protection Features

With the activation of Azure AD Identity protection, organizations benefit from the following features:

Detection

  • Evaluates every sign-in sessions to existing sign-in behavior of the employee
  • Evaluates the User Risk on the overall behavior and detection points
  • Provides custom recommendations to improve overall security posture by highlighting vulnerabilities
  • Integrates with Password protection within Azure AD
    Microsoft obtains from several recourses passwords that are known on the Internet. With this information, Password Protection checks the existing password if the are known on the internet. If so, the user risk becomes high risk within Azure AD Identity protection. Depending on your policies, actions need to be taken before a employee can start working again.

Investigation

  • Provides investigation capabilities
  • Provides an overview of all risk events and/or user accounts.
  • Alerts the security team(s) of events
  • Offers workflow capabilities so admins can
    – Initiate immediate password reset
    – Report false positive events

Risk-based (Conditional Access) policies

  • Provides the capability to request additional user conformation, in sense of a multi-factor authentication or even block access, if a sign-in session is been found risky
  • Provides the capability to request a password reset or even block access, if the user account has been marked to be at risk
  • Integrates with Conditional Access as conditions
  • Enforces MFA registration

Differences in Azure AD Identity Protection functionality between licenses

All the editions of Azure AD provide information on Risk Events and Risky Users. Depending on the edition, more features, information and controls become available.

  • Azure Active Directory Free merely offers a list of users flagged for risk and a overview of risk events.
  • Azure Active Directory Premium (P1) offers more access to the underlying risk events that have been detected for each report.
  • Azure Active Directory Premium P2 offers the most detailed information about all underlying risk events and it also enables organizations to configure security policies that automatically respond to configured risk levels. To enable these policies and response mechanisms, admins need to configure Azure AD Identity Protection.

Note: Azure AD Premium 2 is part of the EMS E5 and Microsoft 365 E5 bundles, but can also be bought separately.

Screenshots of  a Azure AD Free edition risk event and Risky user panel:

RiskEvent-BasTenantRiskyUser-BasTenant

Screenshots of a Azure AD Identity Protection risk event and Risky User details panel:

imageimage

Azure AD Identity Protection Configuration Options (P2-only)

This section shows the configuration options that are available for Azure AD Identity protection:

MFA registration

The first configuration item I want to explain is the ability to manage the MFA registration for the user accounts in use within the organization. This ensures that user accounts that are used to sign in to the Azure AD environment need to have the Azure MFA settings in place in order to continue:

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The settings are stored in the strongauthenticationdetails attribute. These attributes can be reported upon.

User risk

The second configuration item controls what to do if Azure AD Identity Protection calculates that the user risk reaches the Medium or High thresholds. This risk is of the user object itself.

In the example below, the configuration is shown for the situation in which the user risk is High; the affected person need to change the password for his or her account, before he or she can continue working with it.

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Note: When the identities are synchronized for an on-premises environment, it is my advice to enable the self service password reset (SSPR) feature for the Azure AD tenant.

Sign-in risk

The third configuration item governs the action based on the risk level of an actual sign-in session of a user account.

In the example below, the configuration shows that when a sign-in session is calculated to be Medium and above, an additional multi-factor authentication needs to be performed to validate the sign-in attempt:

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Azure AD Identity Protection Alerts (P2-only)

When policies are in place, an administrator also should configure the notification e-mails to the intended department, when a risk level of a user account is calculated to be Medium or higher for example:

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Here’s an example of a notification e-mail and a weekly digest:

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User experience

Let’s look at the result of the configured policies from an end-user perspective, but also with the admin perspective following through.

Risky sign-in

In this example, my test user logs in via a Tor browser and provides his username and password. After clicking Next the sign-in is processed by Azure AD, Conditional Access and Azure AD Identity Protection. Due to a Tor browser being used, the session is marked suspicious and Azure AD asks me to perform an additional MFA challenge, to verify the sign-in attempt:

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After a successful MFA challenge, my test user can continue to use the Office 365 portal:

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Azure AD Identity protection will report this session to the configured recipients in the alert page. And also the event is visible in the report, but marked Closed (resolved) due to the MFA challenge resolution in the policy:

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User Risk sign-in

When a user account hits a risk level of High, the policy states that he or she should change the password for the account before he or she can continue. I recreated the High user risk level by using the Tor browser again to sign-in several times, starting the MFA challenge, but not completing it on all occasions.

In Azure AD Identity Protection the user account is now listed with a High risk level and the password needs to be changed. The configured alert recipients receive another e-mail with the notification that a user is at risk.

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And if the person now tries to login in to the web portal under normal circumstances the following happens:

  1. The person who signs in needs to perform an MFA challenge:
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  2. The person needs to update the password for his or her account:
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  3. After a successful change, the person now has access to his or her Office 365 portal:
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Concluding

Microsoft provides organizations the ability to see if cloud identities are at risk independent of licenses. As an admin, use this to your advantage and take this into account for the health/assessment processes of your environment; include this in your security reports. Additionally, if your tenant is equipped with Azure AD Premium P1 or Premium P2 licenses, ensure you use password protection.

When your Azure AD tenant is using Azure AD Premium P2 licenses, expand your identity defenses with Azure AD Identity Protection. Make use of Microsoft’s knowledge and resources to minimize security breaches.

Enable Valimail Single Sign-On with Azure Active Directory

In my previous blogpost, I described how to enroll Valimail Monitor for Office 365. The initial setup is based on credentials, stored at Valimail. This results in another set of credentials that needs to be remembered, needs to be stored in a password vault, another set that may be leaked…

Additional admins and/or auditors also need to create an additional password for Valimail in order to gain access, adding to the problem.

There must be a better way…

Supported SSO Providers

Valimail has the capability to enable Single sign-on based on SAML2 matching the primary email address of a enabled user:

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As you can see in the below screenshot, they currently support Okta and OneLogin. These SSO Providers have already created an application in their solution.

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I felt it’s random that Azure AD is not listed as an SSO Provider… Microsoft provides Valimail’s services for free to Office 365 tenants; organizations that have Azure AD, too.

I wondered if I could make SSO work in my tenant, using SAML2 authentication. I can say: It works in my tenant! Below are the steps to make it work in your Azure AD tenant, too.

How to make Valimail SSO work with Azure Active Directory

Azure Active Directory doesn’t have Valimail as a listed enterprise application in the application gallery.

However, Microsoft provides the ability to Add your own app (for non-gallery applications), based on SAML-authentication:

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Create an Enterprise App for Valimail in Azure Active Directory

In order to make it work. Write down the company name listed by the account information, on the account settings page on the Valimail webpage. I performed the following steps for Azure Active Directory in the Azure Portal to configure an enterprise application and enable it for SAML2-authentication:

  1. Open a supported browser and navigate to the Azure Portal.
  2. Sign in with an account that has the Global administrator, Application administrator or Cloud application administrator role assigned to it.
  3. Perform multi-factor authentication and/or privileged identity management, if prompted.
  4. Navigate to Azure Active Directory in the left navigation pane.
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  5. In Azure AD’s second navigation pane, click on the Enterprise applications node.
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  6. Click on + New Application.
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  7. Click on the Non-gallery application tile.
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  8. Provide the application name. I choose to name the application Valimail, but your organization’s naming convention may dictate something different.
  9. Click on Add.
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  10. In the new panel that appears, click on Properties.
  11. Set the option: User Assignment required? to No.
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    Note:

    If you decide to limit the number of users that may use the application, leave this option to Yes and assign the users via the Users and groups option.
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  12. Click on Save.
  13. Click on Single sign-on.
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  14. Click on the SAML tile.
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  15. Click on the pencil to the right of the Basic SAML Configuration text to start editing the SAML configuration:
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  16. Configure your Basic SAML Configuration as shown below:
    1. Reconstruct the account information name for example Contoso B.V. to contoso-b-v and use this in the sign-on URL
    2. Identifier (Entity ID): https://app.valimail.com
    3. Reply URL (Assertion Consumer Service URL): https://app.valimail.com/sso/consume
    4. Sign on URL: https://app.valimail.com/sso/accounts/contoso-b-v/sessions/new/
    5. Relay State: https://app.valimail.com/users/sign_in
  17. Click on the Save button and close the panel.
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  18. Click on No, I’ll test later.
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  19. Don’t change anything in User Attributes & Claims. You don’t need to, anyway.
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  20. Download the Federation Metadata XML and save it to a file on your device.
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The configuration of the enterprise application in Azure Active Directory is now complete.

Enable Single Sign-On in Valimail

Now that Azure Active Directory is configured and the federation metadata is stored on the device, it is time to configure Valimail:

  1. Open a supported web browser and navigate to https://app.valimail.com/home.
  2. Provide the email address of a account that has the owner role in Valimail:
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  3. Provide the password for the email address in Valimail:
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  4. Perform 2-factor authentication, if it’s configured.
  5. In the Valimail Portal, click on your name and click on Account settings.
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  6. Click on the Setup button next to Single Sign-on:
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  7. Scroll down to IDP Metadata File field and click on the Browse… button:
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  8. Select and upload the Federation Metadata XML downloaded from Azure Active Directory from your device.
  9. Click on Enable Single Sign-on.
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  10. You’re now automatically signed out.
  11. To sign back in, provide the email address of an account that has the owner role in Valimail.
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  12. Click on Sign in with SSO:
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  13. You’re redirected to Azure Active Directory.
    Depending on your authentication method and configuration, you’re automatically signed in to Azure Active Directory and redirected back to the Valimail Portal:
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  14. Your Valimail application is now configured with Single Sign-on (SSO) using Azure Active Directory.

Conclusion

I feel in every organization the use of a single source of authentication for business applications should be promoted. For SAML, OAuth and OpenID Connect-based authentication, Azure Active Directory is a perfect candidate to be acting as Identity Provider (IdP) for SaaS applications. This reduces the management overhead, especially when a delegated admin leaves the company and the non-Azure Active Directory accounts are improperly registered or are not part of the normal offboarding procedure.

The main benefit of creating a enterprise application within Azure Active Directory is you can apply your organization’s Conditional Access policies. This way, a company can control the access and conditions for employees and even admins to gain access to the application. For instance, if an owner of the Valimail application tries to log on, Conditional Access will trigger multi-factor authentication, if it’s not performed already.

So take 5 minutes of your time and register and activate Single Sign-on for Valimail with Azure Active Directory.

The mysterious case of a failed account recovery and orphaned mailbox

In this blogpost I want to address two real-life cases that I encountered in the same Microsoft Office 365 tenant. The reason why I address the two issues in this one blog is because the errors and steps to resolution, were identical for both issues.

Background Information

The issues occurred in a cloud-only tenant. The tenant has multiple custom domains configured, and in use. The tenant consist of multiple user accounts and shared mailboxes.  There where no external scripts or data sources that are feeding into the Azure AD tenant with account information or automated management tasks.

I was called in to resolve the issues. Names and domains are anonymized for the purpose of this blogpost.

The Issues

Issue 1

The first issue occurred after a user account deletion and recovery.  There were two accounts, that were converted to shared mailboxes.

Mailbox 1: edatorial@custdomainA.com (Primary email) – UPN: edatorial@custdomainA.com – Created in 2017
Mailbox 2: edatorial@custdomainB.com (Primary email) – UPN: edatorial@custdomain.onmicrosoft.com – Created in 2018

The issue here was that mailbox 1 was accidentally deleted. We used the recovery page in the Office 365 Admin Portal to restore this account.
When we did this, we couldn’t change the primary address of both shared mailboxes. We hit an error stating that the proxy address already existed on the other account. On both accounts it was listed as a proxy address in Exchange Online and in Azure AD.
It should be impossible within Exchange Online to have the same proxy address on multiple accounts.

Issue 2

The second issue was that the customer requested a shared mailbox was to be deleted , but the customer asked for a empty shared mailbox with the same name some days later.  This mailbox was created, full access rights were delegated and people started working with the mailbox.

Mailbox 1: tooling@custdomainA.com (Primary email) – UPN: tooling@custdomainA.com

When I was handed the case, the customer reported that they couldn’t access the mailbox anymore. When I looked in Exchange Online, I saw the mailbox still listed on the Shared Mailboxes page.
In the Office 365 Admin Portal, I didn’t see the user account. Instead, it was listed on the Deleted Accounts page. We performed an account restore. This was successful, but not the solution to get it working again.

 

Resolving Issue 1

The information we started with for resolving the issues was that both accounts/mailboxes are visible in the Office 365 Admin Portal and in Exchange Online on the Shared Mailboxes page.

Observations and Symptoms

When both accounts were visible and active again, we tried to manage both accounts from the Exchange Online portal. Mailbox 1 gave an error in the management website; the account wasn’t located on the Domain Controller. Mailbox 2 gave an error, when we tried to alter the proxy addresses; the proxy address already exists on Mailbox 1.

I opened an Exchange Management Shell connection to the tenant, and tried to change the information there. I received the same errors as in the web interface; User not found and proxy address already exists.

“Could this account be incorrectly mapped?”

I checked if the accounts in Azure AD were correctly mapped to the Exchange Online accounts, by changing their display name. Within five minutes the information was updated in Exchange Online. So we know that the mailboxes are correctly mapped to the Azure AD accounts.

Then I remembered the behavior of Exchange Online, that it always wants to add the userPrincipalName (UPN) as an alias on the mailbox and cannot be removed, as long as the UPN is set. But as given in the description the UPNs already were different…

So I listed the mailbox information through the Exchange Online management shell.  Here I discovered that on both mailboxes the attributes WindowsLiveID, and MicrosoftOnlineServicesID, contained the same UPN, edatorial@custdomain.onmicrosoft.com.

Solution

Fixing Mailbox 2

Based on that discovery, I decided to update the UPN of both accounts. First I altered the UPN of mailbox 2, because this mailbox was already set to edatorial@custdomain.onmicrosoft.com . I updated the UPN of Mailbox 2 to edatorial@custdomainB.com and waited on the internal sync of Azure AD and Exchange Online. After five minutes, I checked the attributes WindowsLiveID and MicrosoftOnlineServicesID on Mailbox 2; these where updated to the new UPN information. Then I removed the edatorial@custdomain.onmicrosoft.com as an alias on Mailbox 2. This was successful and no errors were shown.

Mailbox 1 wasn’t fixed after this.

I decided to perform the same action on mailbox 1 as I did on mailbox 2. First I changed the UPN from edatorial@custdomainA.com to edatorial@custdomain.onmicrosoft.com in the Office 365 Admin Portal. Also I changed the display name back to how it was, to see, when the account was updated in Exchange Online. When this was changed, I changed the UPN back from edatorial@custdomain.onmicrosoft.com to edatorial@custdomainA.com in the Office 365 Admin Portal. After five minutes I checked the WindowsLiveID and MicrosoftOnlineServicesID attributes on Mailbox 1; these were updated to the new UPN information. Also it was now possible to manage the mailbox again.

And then…

Something curious happened 15 minutes later, though. Mailbox 1 was deleted again from Exchange Online and Azure AD. When I looked on the Deleted Users page in the Office 365 Admin Portal, the account was listed there again. We initiated a recovery once again and this worked as designed. Now the account was usable and working again. In the audit log of Azure AD, I couldn’t find the delete action, so determining the root cause of that spontaneous deletion was impossible.

Resolving Issue 2

The information for resolving started with that the account was restored in the Azure AD Portal. The mailbox was already visible in Exchange Online.

Observations and Symptoms

After the Azure AD account was restored, I checked if I could manage the mailbox again from the Exchange Online admin page. I only found an error; the object couldn’t be found on the Domain Controller.

As with Issue 1, I checked if the account was correctly mapped to the mailbox. I updated the display name and five minutes later I saw the change in Exchange Online. So I confirmed that the objects were mapped to each other. Based on the experience with Issue 1, I checked if the attributes: WindowsLiveID and MicrosoftOnlineServicesID were the same. This was not the case. The attributes were pointing to tooling@custdomain.onmicrosoft.com instead of tooling@custdomainA.com .

Solution

As solution to this problem I decided to change the userPrincipalName (UPN) from tooling@custdomainA.com to tooling@custdomain.onmicrosoft.com. This time, the change wasn’t picked up by Exchange Online. We already checked the integration, so I decided to delete the user one more time from the Office 365 Admin Portal. Also I waited on Exchange Online to see if the mailbox was deleted from their side. This was the case. So now both the Azure AD account and Mailbox where in a soft delete state.

Going from soft-delete to restored state

Now I restored the Azure AD account from the Office 365 Admin Portal and five minutes later the mailbox was also recovered. This time we could manage the mailbox again. So as the last step in the solution I changed the UPN one more time from tooling@custdomain.onmicrosoft.com to tooling@custdomainA.com  and this was now processed by Exchange Online. The attributes WindowsLiveID and MicrosoftOnlineServicesID were the same as the UPN in Azure AD.

Unknown Root Causes

At time of writing this blog, I still don’t know what caused both issues. 

All management tasks of the tenant are done through the Office 365 Admin Portal and Exchange Online.
The actions I took to resolve Issue 1 were on January 9th. When I was called in to resolve Issue 2, two days later, I saw that this account was deleted on January 9th.

Concluding

If I were to guess, the problem may lay in the  automated recovery procedure and automatic health tasks within Azure AD. I’m still trying to reproduce the issues, to point to a probable cause.

I hope that this blog was informative and useful in the future, when you might come across similar issues.