Authentication fails when email address and UPN do not match

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My concern is that MS will force modern authentication soon, and switch off basic authentication.



modern authentication troubleshooting

Searched till my fingers bled; gave up and installed the free "Windows Outlook", but it was a mess that connection status shows disconnected I can't take. Upgrade to Microsoft Edge to take advantage of the latest features, security updates, and technical support. Windows 10 will reach EOS (end of support) on October 14, 2025.

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If you have an issue that's not listed in this article, go to FixTechGuide Office 365 troubleshooting the following Microsoft TechNet wiki page. The wiki page lists other known issues and workarounds. Since Microsoft recently demanded OAuth2 authentication, I've been trying everything I found here and at Microsoft, but every 'help' webpage to setup Hotmail and Thunderbird seem badly outdated. If the error you are encountering is not listed, please create a ticket on our Email and Calendar Help page for assistance. If memory serves me right, modern auth with 2fa, and being a GA and using the account for outlook are known for issues. So, it looks like the version of Outlook that I have won’t play nice with Modern Authentication.

Troubleshoot sign-in issues with Office modern authentication when you use AD FS



modern authentication troubleshooting

The currently configured authentication methods can remain unchanged. For example, if Windows Integrated Authentication is configured as the primary authentication method, it can remain configured this way. Login to server outlook.office365.com with username [Duck ID]@uoregon.edu failed. Once your account has Modern Authentication enabled, you can no longer pull your UO email into Gmail and/or reply from Gmail on behalf of your UO account. This page contains information on what errors may come up when setting up your email with Modern Authentication (Modern Auth), and what steps are needed to resolve them.

Gmail



  • Upgrade to Microsoft Edge to take advantage of the latest features, security updates, and technical support.
  • This prevents Windows clients that are running Office from logging in as required by the authentication process.
  • We will never ask you to call or text a phone number or share personal information.
  • Is there some kind of setting within O365 that’s forcing Outlook to use basic authentication ?
  • I’ve just switched on Modern Authentication in Office 365, following on from Microsoft’s recommendation.
  • I authorise the applications after installation with modern authentication, and OneDrive client uses it oo, so it looks like it’s only Outlook that’s forcing basic authentication.


This is due to Modern Authentication's ability to support multi-factor authentication (such as Duo), which is better for information security. When this change goes into effect, any email application that uses Basic Authentication may not work properly. This article contains information about how to troubleshoot problems that affect the ability to sign in to Microsoft Office 2016 apps and Microsoft Office 2013 apps that are enabled for modern authentication. This article also contains resources for IT administrators to address reports about Active Directory Federation Services (AD FS) issues that are specific to Office for Windows platforms. (a) I hadn't previously set up 2FA on my Microsoft account, and it seemed to require this.

iOS Mail



Removing and re-adding the account using the standard Sign In method will resolve this error. My concern is that MS will force modern authentication soon, and switch off basic authentication. I therefore have a workaround, but not a solution. Is there some kind of setting within O365 that’s forcing Outlook to use basic authentication ? Other apps are using modern authentication perfectly well, including Teams. I authorise the applications after installation with modern authentication, and OneDrive client uses it oo, so it looks like it’s only Outlook that’s forcing basic authentication.



modern authentication troubleshooting

Please report suspicious activity using the "Report Abuse" option. We recommend using Outlook on the web to check your email or consider configuring a supported email client. I have also followed the troubleshooter in outlook where a MS tech gives you suggestions ( very slowly ). They suggested clearing credentials, which I have already connection status shows disconnected tried. Outlook is working on my phone, and I can access everything via the office.com web site. Now I am constantly being asked to enter passwords for two of my Comcast addresses (my Gmail address works fine).



Outlook 365 Won't Prompt for Modern Authentication



(c) Hotmail syncs with my iPhone, and this stopped working; however, I simply had to re-enter my usual Hotmail password on the phone to get it working again. Similar to Mac Mail, UO email accounts set up in iOS Mail application prior to the Modern Auth update will continue to work provided the device is running iOS 11 or newer. Outlook 2013 supports MA but requires a registry entry as already mentioned. App password is not needed so long as you’re using a modem version of Outlook. To resolve this issue, set up AD FS to use forms-based authentication as the secondary form of authentication. To do this, follow the appropriate steps for the version that you use.
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