Searched till my fingers bled; gave up and installed the free "Windows Outlook", but it was a mess that mailbox not updating on IMAP 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.

Get email updates

If you have an issue that's not listed in this article, go to Fix Outlook and Office365 Sync Issues 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trying everything I found here and at Microsoft, but every 'help' webpage to setup Hotmail and Thunderbird seem badly outdated.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 Helppage 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. Loginto 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 Gmailand/or reply from Gmailon 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

• Once I added the AlwaysUseMSOAuthForAutodiscover value, it popped up the modern auth prompt and worked perfectly.
• Other apps are using modern authentication perfectly well, including Teams.
• I have a couple of PCs that access the system on the same account from Win 10.
• 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trying everything I found here and at Microsoft, but every 'help' webpage to setup Hotmail and Thunderbird seem badly outdated.
• I therefore have a workaround, but not a solution.
• 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.
• To do this, follow the appropriate steps for the version that you use.
• 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.
• I’m going to try & switch modern authentication off to see if that is the issue, although there doesn’t seem to be any way of doing this.

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 phaseout Basic Authentication and replacingit with Modern Authentication.

iOSMail

I have confirmed that on two different PCs that are accessing the same mailbox with the same version of Outlook, which is the latest version from Microsoft included within my Office 365 package. If it continues to be problematic, you may need to either a.) Remove any related credentials from the users credential manager in Control Panel, it b.) Create a new outlook profile. We will never ask you to call or text a phone number or share personal information.

Android Mail

Please report suspicious activity using the "Report Abuse" option. We recommendusing 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 FixTechGuide fix for stuck folders 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

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.