Authentication

How many times you wanted to have Outlook seamless authentication on domain joined computers while connecting to Office 365 like it would do with on premise Exchange? I don't know about you, but I always liked Outlook profile creation without prompting user for entering credentials. This is great feature while Exchange is on-premise since it using either Kerb or NTLM. With moving user mailbox to Office 365, basic authentication for Outlook was only way for authenticating user. Users needed to enter their username / password combination and click 'Save credentials' and everything was fine until user was changed password and prompt would pop up again.

With introduction Modern Authentication for Office suite and Exchange 2016, Outlook seamless authentication experience is possible with Office 365 as well.

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Note // This is only tested with Exchange Hybrid environment.

This post will be divided in three parts:

1. Enable modern authentication on Outlook client,
2. Set up intranet sites for STS,
3. Enable Oauth profiles feature in Office 365.

Enable modern authentication on Outlook client

Modern authentication (ADAL) in Outlook 2016 is enabled by default and it will be first mechanism that Outlook will try to use against Office 365. On the other hand, Outlook 2013 has it turned off by default and registry key should be used for enabling it .

Navigate to HKCU:SoftwareMicrosoftOffice15.0CommonIdentity and create new dword value 'EnableADAL' and set it to value '1':

Set up intranet sites for STS

In order to get seamless experience while authenticating to STS, STS should be placed in 'Local Intranet' zone and that zone should have option 'Automatically login with current username and password' option set:

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Enable Oauth profiles feature in Office 365

Final step in this process is to enable OAuth2 Client Profile. Open PowerShell session to Office365 tenant and execute following command:

Set-OrganizationConfig -OAuth2ClientProfileEnabled $true

After that wait few minutes and you are all set.

Create new Outlook profile (or wait until profile is automatically switch over to OAuth2) for user that have mailbox hosted in Office 365:

You can check in connection status that Outlook is consuming 'Bearer' (fancy name for Oauth) authentication:

How it works? Lets go fiddling..

I won't cover each step Outlook performs while connecting to service (you should know it already!?), just one's that matters. Fire up Fiddler!

1. Client make HTTP POST to https://autodiscover-s.outlook.com/autodiscover/autodiscover.xml

Response: 401 Unauthorized with authorization link https://login.windows.net/common/oauth2/authorize

2. Client submits HTTP GET against login.microsoft.com and request contains user email address: Update mac 10.10.

Microsoft Modern Authentication Ios

Request:

Response (redirect to OnPrem STS):

3. STS authenticate client and return it back to login.microsoft.com:

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This article applies to both Office 365 Enterprise and Microsoft 365 Enterprise.

Microsoft Teams Mac Modern Authentication Failed Windows 10

Modern Authentication enables Active Directory Authentication Library (ADAL)-based sign-in for Office client apps across different platforms. This enables sign-in features such as Multi-Factor Authentication (MFA), smart card, and certificate-based authentication.

Learn more about multi-factor authentication and certificate-based authentication.

Supported platforms

Microsoft Teams Mac Modern Authentication Failed Update

  • Windows 10 Desktop
  • Windows 10 Modern Apps
  • Web browsers1
  • Android2
  • iOS
  • macOS

For more information about platform support in Office 365, see System requirements for Office 365.

Supported clients

The latest versions of the following clients support modern authentication:


Access
Azure
Portal
Company
Portal
Delve
Dynamics 365

Edge
Excel
Flow
Forms
Kaizala

Office.com
Office 365
Admin
Office Lens
OneDrive
OneNote

Outlook
Planner
PowerApps
Power BI
PowerPoint

Project
Publisher
Sharepoint
Skype for
Business1
StaffHub

Sticky Notes
Stream
Sway
Teams
To Do

Visio
Whiteboard1,2
Word
Yammer
Yammer
Notifier

Supported PowerShell modules


Azure AD
PowerShell
Exchange Online
PowerShell
SharePoint Online
PowerShell

Microsoft Teams Mac Modern Authentication Failed Version

Note

1 Support for Whiteboard and Skype for Business on web app available soon.
2 Support for Whiteboard on Android available soon.

Enable Modern Authentication For Teams

See also