Outlook Web Access (OWA) and on-premises Exchange Single Sign-On (SSO) using Microsoft Entra

Outlook Web Access (OWA) SSO (Single Sign-On) solution by miniOrange provides seamless SSO to your Outlook Web Access (OWA) Application and on-premises Exchange server for secure SSO login. With miniOrange’s OWA SSO configuration, your users will be able to login to Outlook Web Access (OWA) and other SaaS or on-premises applications with your existing IDP credentials. miniOrange’s Outlook web access SSO provides IDP integration with ADFS, Okta, Onelogin, Microsoft Azure Active Directory, AWS Cognito etc. You can also connect miniOrange’s solution with Active Directory, LDAP, Google or use miniOrange as your directory in the cloud. We support multiple protocols like SAML,OAuth, LDAP, OIDC etc.

miniOrange and Outlook Web Access (OWA) Single Sign-On (SSO) integration supports the following features:

SP (Service Provider) Initiated Single Sign-On (SSO)

In this flow, the user tries to login to the Service Provider (On-Premises Exchange OWA Outlook Web Access account) directly. The request is redirected to the Identity Provider (Microsoft Entra, etc.) for authentication. On sucessfull authentication from the Identity provider, the user is given access to the application (OWA account).

IdP (Identity Provider) Initiated Single Sign-On (SSO)

In this flow, the user logs in to the Identity Provider (Microsoft Entra, etc.) using his credentials. Now the user can access any of the configured Service Providers (OWA account, etc.) through the Identity Provider Dashboard without having to enter the credentials agian.

Connect with External Source of Users

miniOrange provides user authentication from various external sources, which can be Directories (like ADFS, Microsoft Active Directory, Azure AD, OpenLDAP, Google, AWS Cognito etc), Identity Providers (like Shibboleth, Ping, Okta, OneLogin, KeyCloak), Databases (like MySQL, Maria DB, PostgreSQL) and many more.

Prerequisites

All plans are required to do the single sign-on (SSO) configuration.

Follow the step-by-step guide given below for Outlook Web Access (OWA) Single Sign-On (SSO)

1. Configure Exchange in miniOrange IdP

Login into miniOrange dashboard from the Admin Console.
From the left side menu, click on Apps → Manage Apps.

Exchange OWA Single Sign-on (SSO) manage apps

Click on Add Application button.

Outlook Web Access Single Sign-On (SSO) add app

In choose application type, click on create app button in SAML/WS-FED application type.

In the next step, search for your application from the list, if your application is not found. Search for "custom" and you can set up your app via Custom WS-Fed App.

Exchange OWA Single Sign-on (SSO) select SAML tab

Enter the following information in the respective fields.

Custom Application Name: Outlook Web access Owa
WT-Realm: https://{owa-url} e.g. https://mail.example.com/owa
Reply URL: https://{owa-url} e.g. https://mail.example.com/owa
Set WS-Fed validity period: 300s

SharePoint On-premise Single Sign-On (SSO) manage apps

Under Attribute Mapping section, enter the following attributes as shown below:

Click on Save.

2. Configure Exchange / OWA for Sign-On using miniOrange

After saving the app, go to Apps and click on Select >> Metadata against the app saved.

Select Show Metadata Details to reveal the details shown in the image below.

Copy the WS-Federation Reply URL and download the X.509 Certificate.
Add above certificate (obtained in above step) to the Trusted People store on the Exchange Server using the steps below:

Got to Management Console. Open run dialog (Win + R) and type mmc and press enter.
In Management Console, go to File > Add or Remove Snap-ins (Ctrl + M).
Search for Certificates on the left side and press Add.
In the Certificate Snap In window, select Computer account and press Next. Then select Local Computer and press Finish.
You will see an entry for Certificates (Local Computer) in the right pane. Click OK to close the Add or Remove Snap-ins window.
You will see a branch named Certificates created under Console Root. Expand the Certificates branch and select Trusted People.
Right click on Trusted People > Find > Import and click on Next.
Choose the location of the downloaded certificate file you created above and click on Next, again Next and Finish.
You have successfully added a Signing Certificate to Trusted People. Now close Management Console and choose No on the Save data prompt.

Execute the commands below on the Exchange Server using the Exchange Management Shell.
In the below command, ##Base URL## is the exchange/OWA host. The command has both URLs: One ending in / and the other one which does not contain a trailing slash.
$uris=@("https://##Base URL##/owa/","https://##Base URL##/ecp/","https://##Base URL##/owa","https://##Base URL##/ecp")
In the below command, the ##miniOrange URL## is the WS-Federation Reply URL. The Cert Thumbprint is the SHA-1 thumbprint of the certificate you downloaded.
Note: Make sure the certificate thumb print is in uppercase.

Set-OrganizationConfig -AdfsIssuer "##miniOrange URL##" -AdfsAudienceUris $uris -AdfsSignCertificateThumbprint ##Cert Thumbprint##
Get-EcpVirtualDirectory | Set-EcpVirtualDirectory -AdfsAuthentication $true -BasicAuthentication $false -DigestAuthentication $false -FormsAuthentication $false -WindowsAuthentication $false
Get-OwaVirtualDirectory | Set-OwaVirtualDirectory -AdfsAuthentication $true -BasicAuthentication $false -DigestAuthentication $false -FormsAuthentication $false -WindowsAuthentication $false -OAuthAuthentication $false
# Restart w3svc and was net stop was /y net start w3svc

3. Test SSO Configuration

Login to your OWA account.
You will be redirected to miniOrange IdP Sign On page.

Enter your miniOrange login credential and click on Login. You will be automatically logged in to your account.

4. Configure Your User Directory (Optional)

miniOrange provides user authentication from various external sources, which can be Directories (like ADFS, Microsoft Active Directory, Microsoft Entra ID, OpenLDAP, Google, AWS Cognito etc), Identity Providers (like Okta, Shibboleth, Ping, OneLogin, KeyCloak), Databases (like MySQL, Maria DB, PostgreSQL) and many more. You can configure your existing directory/user store or add users in miniOrange.

Setup miniOrange as IDP
Setup AD as User Directory
Setup External IDP

To add your users in miniOrange there are 2 ways:

1. Create User in miniOrange

2. Bulk Upload Users

1. Create User in miniOrange

Click on Users >> User List >> Add User.

Here, fill the user details without the password and then click on the Create User button.

After successful user creation a notification message "An end user is added successfully" will be displayed at the top of the dashboard.

Click on Onboarding Status tab. Check the email, with the registered e-mail id and select action Send Activation Mail with Password Reset Link from Select Action dropdown list and then click on Apply button.

Now, Open your email id. Open the mail you get from miniOrange and then click on the link to set your account password.
On the next screen, enter the password and confirm password and then click on the Single Sign-On (SSO) reset password button.

Now, you can log in into miniOrange account by entering your credentials.

2. Bulk Upload Users in miniOrange via Uploading CSV File.

Navigate to Users >> User List. Click on Add User button.

In Bulk User Registration Download sample csv format from our console and edit this csv file according to the instructions.

To bulk upload users, choose the file make sure it is in comma separated .csv file format then click on Upload.

After uploading the csv file successfully, you will see a success message with a link.
Click on that link you will see list of users to send activation mail. Select users to send activation mail and click on Send Activation Mail. An activation mail will be sent to the selected users.

Click on External Directories >> Add Directory in the left menu of the dashboard.

Select Directory type as AD/LDAP.

STORE LDAP CONFIGURATION IN MINIORANGE: Choose this option if you want to keep your configuration in miniOrange. If active directory is behind a firewall, you will need to open the firewall to allow incoming requests to your AD.
STORE LDAP CONFIGURATION ON PREMISE: Choose this option if you want to keep your configuration in your premise and only allow access to AD inside premises. You will have to download and install miniOrange gateway in your premise.

Enter LDAP Display Name and LDAP Identifier name.
Select Directory Type as Active Directory.
Enter the LDAP Server URL or IP Address against LDAP Server URL field.
Click on Test Connection button to verify if you have made a successful connection with your LDAP server.

Outlook: Configure LDAP server URL Connection

In Active Directory, go to the properties of user containers/OU's and search for Distinguished Name attribute.

Outlook: Configure user bind account domain name

Enter the valid Bind account Password.
Click on Test Bind Account Credentials button to verify your LDAP Bind credentials for LDAP connection.

Search Base is the location in the directory where the search for a user begins. You will get this from the same place you got your Distinguished name.

Select a suitable Search filter from the drop-down menu. If you use User in Single Group Filter or User in Multiple Group Filter, replace the <group-dn> in the search filter with the distinguished name of the group in which your users are present. To use custom Search Filter select "Write your Custom Filter" option and customize it accordingly.

You can also configure following options while setting up AD. Enable Activate LDAP in order to authenticate users from AD/LDAP. Click on the Save button to add user store.

Here's the list of the attributes and what it does when we enable it. You can enable/disable accordingly.

Attribute	Description
Activate LDAP	All user authentications will be done with LDAP credentials if you Activate it
Sync users in miniOrange	Users will be created in miniOrange after authentication with LDAP
Fallback Authentication	If LDAP credentials fail then user will be authenticated through miniOrange
Allow users to change password	This allows your users to change their password. It updates the new credentials in your LDAP server
Enable administrator login	On enabling this, your miniOrange Administrator login authenticates using your LDAP server
Show IdP to users	If you enable this option, this IdP will be visible to users
Send Configured Attributes	If you enable this option, then only the attributes configured below will be sent in attributes at the time of login

Click on Save. After this, it will show you the list of User stores. Click on Test Connection to check whether you have enter valid details. For that, it will ask for username and password.

On Successful connection with LDAP Server, a success message is shown.
Click on Test Attribute Mapping.

Enter a valid Username. Then, click on Test. Mapped Attributes corresponding to the user are fetched.

Outlook: Fetch mapped attributes for user

After successful Attribute Mapping Configuration, go back to the ldap configuration and enable Activate LDAP in order to authenticate users from AD/LDAP.

Refer our guide to setup LDAPS on windows server.

User Import and Provisioning from AD

Go to Settings >> Product Settings in the Customer Admin Account.

MFA/Two-Factor Authentication(2FA) for miniOrange dashboard

Enable the "Enable User Auto Registration" option and click Save.

MFA/Two-Factor Authentication(2FA) for Enable User Auto Registration

(Optional) To send a welcome email to all the end users that will be imported, enable the "Enable sending Welcome Emails after user registration" option and click Save.

MFA/Two-Factor Authentication(2FA) for Enable sending Welcome Emails after user registration

From the Left-Side menu of the dashboard select Provisioning.

MFA/Two-Factor Authentication(2FA) for User Sync/Provisioning

In Setup Provisioning tab select Active Directory in the Select Application drop-down.
Toggle the Import Users tab, click on Save button.

MFA/Two-Factor Authentication(2FA) for User Sync Active Directory Configuration

On the same section, switch to Import Users section.
Select Active Directory from the dropdown and click on the Import Users tab, to import all the users from Active Directory to miniOrange.

MFA/Two-Factor Authentication(2FA) for User Sync Import Operation

You can view all the Users you have imports by selecting Users >> User List from Left Panel.

MFA/Two-Factor Authentication(2FA) for User List

All the imported users will be auto registered.
These groups will be helpful in adding multiple 2FA policies on the applications.

miniOrange integrates with various external user sources such as directories, identity providers, and etc.

Not able to find your IdP or Need help setting it up?

Contact us or email us at idpsupport@xecurify.com and we'll help you setting it up in no time.

5. Adaptive Authentication with Outlook

A. Restricting access to Outlook with IP Blocking

You can use adaptive authentication with Outlook Single Sign-On (SSO) to improve the security and functionality of Single Sign-On. You can allow a IP Address in certain range for SSO or you can deny it based your requirements and you can also challenge the user to verify his authenticity. Adaptive authentication manages the user authentication bases on different factors such as Device ID, Location, Time of Access, IP Address and many more.

You can configure Adaptive Authentication with IP Blocking in following way:

Login to Self Service Console >> Adaptive Authentication.
Add a Policy Name for your Adaptive Authentication Policy.

Outlook Single Sign-On (SSO) Restrict Access adaptive authentication policy

Select your Action for behavior Change and Challenge Type for user from the Action for behavior Change Section.

Outlook Single Sign-On (SSO) Restrict Access adaptive authentication behavior change

Action for behavior Change Options :

Attribute	Description
Allow	Allow user to authenticate and use services if Adaptive authentication condition is true.
Challenge	Challenge users with one of the three methods mentioned below for verifying user authenticity.
Deny	Deny user authentications and access to services if Adaptive authentication condition is true.

Challenge Type Options :

Attribute	Description
User second Factor	The User needs to authenticate using the second factor he has opted or assigned for such as OTP over SMS PUSH Notification OTP over Email And 12 more methods.
KBA (Knowledge-based authentication)	The System will ask user for 2 of 3 questions he has configured in his Self Service Console. Only after right answer to both questions user is allowed to proceed further.
OTP over Alternate Email	User will receive a OTP on the alternate email he has configured threw Self Service Console. Once user provides the correct OTP he is allowed to proceed further.

Now Enable Enable IP Restriction option from the IP RESTRICTION CONFIGURATION section to configure custom IP range.

Outlook Single Sign-On (SSO) Restrict Access adaptive authentication ip blocking

Select the Action you want to perform if the IP address is out of the range. i.e. Allow, Challenge & Deny.
Specify the IP Address range for which you want above setting to reflect. You can add more than one IP Address ranges by clicking on following button +.
Scroll to the end and click on save.

B. Adaptive Authentication with Limiting number of devices.

Using Adaptive Authentication you can also restrict the number of devices the end user can access the Services on. You can allow end users to access services on a fixed no. of devices. The end users will be able to access services provided by us on this fixed no. of devices.

You can configure Adaptive Authentication with Device Restriction in following way

Login to Self Service Console >> Adaptive Authentication.
Add a Policy Name for your Adaptive Authentication Policy.
Select your Action for behavior Change and Challenge Type for user from the Action for behavior Change Section.

Outlook Single Sign-On (SSO) Restrict Access adaptive authentication behavior and challenge type

Scroll down to Device Configuration section and enable Allow User to Register Device option to allow users to register their devices.
Enter the Number of Devices which are allowed to register in field next to Number of Device Registrations Allowed
Choose Action if number of devices exceeded (This will override your setting for Action for behavior Change.)

Challenge: The user needs to verify himself using any of the three methods mentioned in table in step 5.1
Deny : Deny users access to the system

Enable option Send email alerts to Users if number of Device registrations exceeded allowed count if you want to alert the user about no of devices exceeding the limit. Save the configuration.

Outlook Single Sign-On (SSO) Restrict Access adaptive authentication enable device restriction

C. Add Adaptive Authentication policy to Outlook.

Login to Self Service Console >> Policies.
Click on Edit option for predefined app policy.

Outlook Single Sign-On (sso) edit device restriction policy

Set your application name in the Application and select password as Login Method.
Enable Adaptive Authentication on Policy page and select the required restriction method as an option.
From Select Login Policy dropdown select the policy we created in last step and click on save.

Outlook Single Sign-On (SSO) Restrict Access save device restriction policy

D.Notification and Alert Message.

This section handles the notifications and alerts related to Adaptive Authentication.It provides the following options :

Get email alerts if users login from unknown devices or locations : Admin need to enable this option to enable receiving alerts for different alert options.

Option	Description
Challenge Completed and Device Registered	Enabling this option allows you to send an email alert when an end-user completes a challenge and registers a device.
Challenge Completed but Device Not Registered	Enabling this option allows you to send an email alert when an end-user completes a challenge but do not registers the device.
Challenge Failed	Enabling this option allows you to send an email alert when an end-user fails to complete the challenge.

adaptive authentication Action for behavior Change Configuration

Next subsection is Send email alerts which allows us to enable or disable alerts for admin and end-users. To enable alerts for admins, you can enable the “Administrators” switch button.

In case you want multiple admins accounts to receive alerts then you can enable the option for admin and then enter the admin emails separated by a ‘,’ in the input field next to Administrators email to receive alerts label. To enable alerts for the end-users, you can enable the “End Users” switch button.
In case you want to customize the deny message that end user receive in case his authentication denied due to adaptive policy, you can do this by entering the message inside “Deny message for Adaptive Authentication” text box.

How to add a trusted Device

When End-user log in to the self service console after the policy for device restriction is on, he is provided the option to add the current device as a trusted device.

External References

FAQ

How to disable miniOrange Login for Exchange?

You can run the below commands in Exchange Management Shell to disable federation with miniOrange and enable Forms based authentication.

Get-OwaVirtualDirectory | Set-OwaVirtualDirectory -AdfsAuthentication $false
        -BasicAuthentication $false -DigestAuthentication $false -FormsAuthentication $true
        -WindowsAuthentication $false -OAuthAuthentication $false

Get-EcpVirtualDirectory | Set-EcpVirtualDirectory -AdfsAuthentication $false
        -BasicAuthentication $false -DigestAuthentication $false -FormsAuthentication $true
        -WindowsAuthentication $false

# Restart w3svc and was
net stop was /y
net start w3svc

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