Searched till my fingers bled; gave up and installed the free "Windows Outlook", but it was a mess that Exchange connectivity diagnostic 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 work offline mode stuck 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trying everything I found here and at Microsoft, but every 'help' webpage to setup Hotmail and Thunderbird seem badly outdated.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

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

• This issue has been resolved by having users connect to the UO VPN when initially setting up their account with Mac Mail.
• Outlook is working on my phone, and I can access everything via the office.com web site.
• UO email accounts set up in Mac Mail prior to the Modern Auth update will continue to work, provided the device is running macOS 10.14 or newer.
• When this change goes into effect, any email application that uses Basic Authentication may not work properly.
• If issues are encountered, it is advised to first re-setup the account in Mac Mail.

I have a couple of PCs that access the system on the same account from Win 10. Both are affected in the same way in that Outlook is constantly asking for a username & password ( not using the modern authentication dialogue box ). I’ve tried various registry changes that I’ve found from Googling, tried changing the password, tried re-installing Office and also enabling & disabling MFA. Microsoft will soon phase out Basic Authentication and replacing it with Modern Authentication.

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.





I’m going to try & switch modern authentication off to see if that is rebuild Outlook data file quickly the issue, although there doesn’t seem to be any way of doing this. It does look llike a one-time thing to switch it on. I’m quite fortunate that this is just my O365 instance, so customers not being impacted. Desktop SSO is the process that's used to obtain seamless sign-in to Microsoft 365 resources through AD FS from a domain-joined computer that's inside a company network. When desktop SSO fails, users may be unable to activate Microsoft 365 Apps for enterprise or users may be prompted for forms-based logon even though they are using domain joined-computers from inside the company network.

Outlook 365 Won't Prompt for Modern Authentication

Create your account and connect with a world of communities. Once I added the AlwaysUseMSOAuthForAutodiscover value, it popped up the modern auth prompt and worked perfectly. I’ve just switched on Modern Authentication in Office 365, following on from Microsoft’s recommendation.