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This is one of the limitations of Outlook's new functionality. Those with Outlook installed on their mobile devices may use it soon to verify the second authentication step, at least when it comes to Microsoft product authentications. A plausible reason is to reduce the complexity somewhat for users. Microsoft does not reveal why it is integrating authentication functionality into Outlook. In my case Outlook 2016 now workes fine with 2FA enabled.The decision to integrate the functionality into Outlook may sound superfluous to Microsoft Authenticator users, but these are probably not the target audience.

Now we need to determine which applications will send the correct authentication. OK, now your tenant will accept Modern Authentication requests. Set-OrganizationConfig -OAuth2ClientProfileEnabled:$true This will present a lot of info but the part we are interested in is illustrated below:Īs you can see, OAuth2ClientProfileEnabled is set to False. This means Modern Authentication is disabled for Exchange Online. Skype for Business Modern Authentication has just come out of public preview.įirst of all connect your PowerShell to Exchange Online in your Office 365 tenant, then run the following command: Get-OrganizationConfig The solution is enabling Modern Authentication which is disabled by default for Exchange Online but enabled by default for SharePoint Online. Now, not everybody likes using app passwords since they are hard to manage and will place an extra workload on your Helpdesk. Each user gets an App Password to use for any applications that do not support Modern Authentication or any applications that are not enabled for Modern Authentication. If you use Azure MFA as your multi-factor solution, Microsoft provide a workaround for the password loop problem.

The issue is caused by a requirement for ‘Modern Authentication’ to be enforced.

I recently had a major issue where a client was seeing constant password prompts when multi-factor authentication (MFA) was enabled for access to Office 365 with his Outlook 2016 client.