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Christian Taveras
Iron Contributor
Oct 16, 2017

Multi-factor Authentication breaks outlook

Just wondering if anyone has run into this issue.     I have been Turning on MFA for users a group at a time all was going smooth.  The next morning after turning on MFA for the last hand full of u...

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This is the place to discuss best practices, latest trends and news for topics related to Microsoft 365.\n\n

For technical support and break/fix questions, please visit Microsoft Support Community.
\nFor help & learning (how-to articles, videos, training), please visit Microsoft Support.

","avatar":null,"profileSettings":{"__typename":"ProfileSettings","language":null},"parent":{"__ref":"Category:category:microsoft365"},"ancestors":{"__typename":"CoreNodeConnection","edges":[{"__typename":"CoreNodeEdge","node":{"__ref":"Community:community:gxcuf89792"}},{"__typename":"CoreNodeEdge","node":{"__ref":"Category:category:communities"}},{"__typename":"CoreNodeEdge","node":{"__ref":"Category:category:products-services"}},{"__typename":"CoreNodeEdge","node":{"__ref":"Category:category:microsoft365"}}]},"userContext":{"__typename":"NodeUserContext","canAddAttachments":false,"canUpdateNode":false,"canPostMessages":false,"isSubscribed":false},"boardPolicies":{"__typename":"BoardPolicies","canPublishArticleOnCreate":{"__typename":"PolicyResult","failureReason":{"__typename":"FailureReason","message":"error.lithium.policies.forums.policy_can_publish_on_create_workflow_action.accessDenied","key":"error.lithium.policies.forums.policy_can_publish_on_create_workflow_action.accessDenied","args":[]}}},"shortTitle":"Microsoft 365","repliesProperties":{"__typename":"RepliesProperties","sortOrder":"REVERSE_PUBLISH_TIME","repliesFormat":"threaded"},"tagProperties":{"__typename":"TagNodeProperties","tagsEnabled":{"__typename":"PolicyResult","failureReason":null}},"requireTags":true,"tagType":"PRESET_ONLY","eventPath":"category:microsoft365/category:products-services/category:communities/community:gxcuf89792board:microsoft-365/"},"Rank:rank:35":{"__typename":"Rank","id":"rank:35","position":15,"name":"Iron Contributor","color":"333333","icon":null,"rankStyle":"TEXT"},"User:user:87754":{"__typename":"User","id":"user:87754","uid":87754,"login":"Christian Taveras","deleted":false,"avatar":{"__typename":"UserAvatar","url":"https://techcommunity.microsoft.com/t5/s/gxcuf89792/images/dS04Nzc1NC0zNjQ0OGkzNjRCQ0RBNTMzQjdENjY2"},"rank":{"__ref":"Rank:rank:35"},"email":"","messagesCount":114,"biography":null,"topicsCount":29,"kudosReceivedCount":31,"kudosGivenCount":5,"kudosWeight":1,"registrationData":{"__typename":"RegistrationData","status":null,"registrationTime":"2017-10-16T11:54:11.335-07:00","confirmEmailStatus":null},"followersCount":null,"solutionsCount":1},"ForumTopicMessage:message:116984":{"__typename":"ForumTopicMessage","uid":116984,"subject":"Multi-factor Authentication breaks outlook","id":"message:116984","revisionNum":1,"repliesCount":44,"author":{"__ref":"User:user:87754"},"depth":0,"hasGivenKudo":false,"board":{"__ref":"Forum:board:microsoft-365"},"conversation":{"__ref":"Conversation:conversation:116984"},"readOnly":false,"editFrozen":false,"moderationData":{"__ref":"ModerationData:moderation_data:116984"},"body@stripHtml({\"truncateLength\":200})":" Just wondering if anyone has run into this issue.     I have been Turning on MFA for users a group at a time all was going smooth.  The next morning after turning on MFA for the last hand full of u...","body@stringLength":"812","rawBody":"

Just wondering if anyone has run into this issue.  

 

I have been Turning on MFA for users a group at a time all was going smooth.  The next morning after turning on MFA for the last hand full of users I had to force a password change company wide due to an internal issue.  After doing this it caused outlook to start prompting only for the last hand full of users.  No matter which password was entered it continued to prompt.  I tried the domain credentials and i even popped in the app password as I read an article that mentioned this but this did not work for me.  Just wondering if anyone has run into something similar or can shed any light that may have caused this issue while i wait for 2nd level support to call me.

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Just wondering if anyone has run into this issue.  

 

I have been Turning on MFA for users a group at a time all was going smooth.  The next morning after turning on MFA for the last hand full of users I had to force a password change company wide due to an internal issue.  After doing this it caused outlook to start prompting only for the last hand full of users.  No matter which password was entered it continued to prompt.  I tried the domain credentials and i even popped in the app password as I read an article that mentioned this but this did not work for me.  Just wondering if anyone has run into something similar or can shed any light that may have caused this issue while i wait for 2nd level support to call me.

"},"Conversation:conversation:116984":{"__typename":"Conversation","id":"conversation:116984","solved":false,"topic":{"__ref":"ForumTopicMessage:message:116984"},"lastPostingActivityTime":"2022-03-01T04:26:55.767-08:00","lastPostTime":"2022-03-01T04:26:55.767-08:00","unreadReplyCount":44,"isSubscribed":false},"ModerationData:moderation_data:116984":{"__typename":"ModerationData","id":"moderation_data:116984","status":"APPROVED","rejectReason":null,"isReportedAbuse":false,"rejectUser":null,"rejectTime":null,"rejectActorType":null},"Revision:revision:116984_1":{"__typename":"Revision","id":"revision:116984_1","lastEditTime":"2017-10-16T12:36:02.801-07:00"},"ForumReplyMessage:message:1205810":{"__typename":"ForumReplyMessage","id":"message:1205810","conversation":{"__ref":"Conversation:conversation:116984"},"author":{"__ref":"User:user:572921"},"revisionNum":5,"uid":1205810,"depth":3,"hasGivenKudo":false,"subscribed":false,"board":{"__ref":"Forum:board:microsoft-365"},"subject":"Re: Multi-factor Authentication breaks outlook","readOnly":false,"editFrozen":false,"moderationData":{"__ref":"ModerationData:moderation_data:1205810"},"parent":{"__ref":"ForumReplyMessage:message:983680"},"body":"

Christian Taveras years later (though this thread was still active only a couple of months ago) I have one more potential culprits and an actual solution versus a work around/hack - for everyone's sake hopefully its the solution once and for all, as it should take you 5 minutes to make a single global change.

 

The solution came from continual link following from one of the replies above to Microsoft, back to other forums and in a loop but I pieced together the actual problem and was able to then find the solution. I figured I'd post this to help someone to cut to the chase versus having to following the same rabbit hole I did. I tried SaRA to no avail (just like with a couple of your tenants) and recreating the windows profile was the only solution that seemed reliable - not really an organization wide option.

 

I noticed, like you, I had a problem with some users, not all.  I subsequently identified these users were all older tenants.  I then found an article from Microsoft that said \"For tenants created before August 1, 2017, modern authentication is turned off by default for Exchange Online and Skype for Business Online.\"

 

Essentially, try as you may with local options when your tenant attempts to authenticate with Exchange Online, O365 is forcing Outlook to use basic auth, not modern auth. So your \"switch flicking\" from SaRA did something server side not local or it changed something in the local registry that ignored O365 asking for Basic Auth. This could explain why registry hacks work. Andrios, iOS, and OSX applications only have modern auth so they cannot have the problem (\":facepalm:\" only the application native to a Microsoft Operating system).

 

Solution... force all users to Modern Authentication. In retrospect this makes sense as I've noticed new users always got the modern auth prompt even before trying to implement MFA while the old timers like myself had basic auth prompts still pop up occasionally.

 

Note: this assumes you are on 2016/Outlook for Office 365, 2013 users still additionally have to enable ADAL with registry changes first, then you follow the instructions below to enable modern auth with Exchange Online-> https://support.office.com/en-us/article/enable-modern-authentication-for-office-2013-on-windows-devices-7dc1c01a-090f-4971-9677-f1b192d6c910

 

Solution in detail:

 

Run Powershell - here is another gotcha, in a fun Microsoft twist of irony if you have MFA enabled for this user you will have to download the Microsoft Exchange Online Remote Powershell Module to get modern auth in the powershell environment.  If your username can log in with basic auth, search->powershell->run as admin.

 

Connect to Exchange Online in PowerShell

Connect-EXOPSSession -UserPrincipalName chris@contoso.com   

(for US based Office 365 - for others, you will need to find the URIs)

 

Enable Modern Authentication in Exchange Online

Set-OrganizationConfig -OAuth2ClientProfileEnabled $true  

 

Check Status of Modern Authentication

Get-OrganizationConfig | Format-Table Name,OAuth* -Auto

 

PS C:\\Users\\StevenOsuch> Set-OrganizationConfig -OAuth2ClientProfileEnabled $true
PS C:\\Users\\StevenOsuch> Get-OrganizationConfig | Format-Table Name,OAuth* -Auto

              Name                                        OAuth2ClientProfileEnabled
                ----                                               --------------------------
domain.somewhere.com                                            True

 

 

Now open up Outlook, it worked instantly, I didn't even have to provide credentials as it pulled it from my laptop which already had the SSO profile that had been authenticated at login.

 

Retrospectively, looking at the Set-Up MFA for O365 article (https://docs.microsoft.com/en-us/microsoft-365/admin/security-and-compliance/set-up-multi-factor-authentication?view=o365-worldwide), it mentions this as well but this was just updated a couple of days ago so maybe it wasn't there before.

 

Final note, if you still use Skype for Business, you have to enable Modern Auth separately using the Skype specific connection and command prompts.

 

","body@stringLength":"5935","rawBody":"

 years later (though this thread was still active only a couple of months ago) I have one more potential culprits and an actual solution versus a work around/hack - for everyone's sake hopefully its the solution once and for all, as it should take you 5 minutes to make a single global change.

 

The solution came from continual link following from one of the replies above to Microsoft, back to other forums and in a loop but I pieced together the actual problem and was able to then find the solution. I figured I'd post this to help someone to cut to the chase versus having to following the same rabbit hole I did. I tried SaRA to no avail (just like with a couple of your tenants) and recreating the windows profile was the only solution that seemed reliable - not really an organization wide option.

 

I noticed, like you, I had a problem with some users, not all.  I subsequently identified these users were all older tenants.  I then found an article from Microsoft that said \"For tenants created before August 1, 2017, modern authentication is turned off by default for Exchange Online and Skype for Business Online.\"

 

Essentially, try as you may with local options when your tenant attempts to authenticate with Exchange Online, O365 is forcing Outlook to use basic auth, not modern auth. So your \"switch flicking\" from SaRA did something server side not local or it changed something in the local registry that ignored O365 asking for Basic Auth. This could explain why registry hacks work. Andrios, iOS, and OSX applications only have modern auth so they cannot have the problem ( only the application native to a Microsoft Operating system).

 

Solution... force all users to Modern Authentication. In retrospect this makes sense as I've noticed new users always got the modern auth prompt even before trying to implement MFA while the old timers like myself had basic auth prompts still pop up occasionally.

 

Note: this assumes you are on 2016/Outlook for Office 365, 2013 users still additionally have to enable ADAL with registry changes first, then you follow the instructions below to enable modern auth with Exchange Online-> https://support.office.com/en-us/article/enable-modern-authentication-for-office-2013-on-windows-devices-7dc1c01a-090f-4971-9677-f1b192d6c910

 

Solution in detail:

 

Run Powershell - here is another gotcha, in a fun Microsoft twist of irony if you have MFA enabled for this user you will have to download the Microsoft Exchange Online Remote Powershell Module to get modern auth in the powershell environment.  If your username can log in with basic auth, search->powershell->run as admin.

 

Connect to Exchange Online in PowerShell

Connect-EXOPSSession -UserPrincipalName chris@contoso.com   

(for US based Office 365 - for others, you will need to find the URIs)

 

Enable Modern Authentication in Exchange Online

Set-OrganizationConfig -OAuth2ClientProfileEnabled $true  

 

Check Status of Modern Authentication

Get-OrganizationConfig | Format-Table Name,OAuth* -Auto

 

PS C:\\Users\\StevenOsuch> Set-OrganizationConfig -OAuth2ClientProfileEnabled $true
PS C:\\Users\\StevenOsuch> Get-OrganizationConfig | Format-Table Name,OAuth* -Auto

              Name                                        OAuth2ClientProfileEnabled
                ----                                               --------------------------
domain.somewhere.com                                            True

 

 

Now open up Outlook, it worked instantly, I didn't even have to provide credentials as it pulled it from my laptop which already had the SSO profile that had been authenticated at login.

 

Retrospectively, looking at the Set-Up MFA for O365 article (https://docs.microsoft.com/en-us/microsoft-365/admin/security-and-compliance/set-up-multi-factor-authentication?view=o365-worldwide), it mentions this as well but this was just updated a couple of days ago so maybe it wasn't there before.

 

Final note, if you still use Skype for Business, you have to enable Modern Auth separately using the Skype specific connection and command prompts.

 

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Christian Taveras 

 

Please be aware that Microsoft has announced that it is going to forbid App passwords (i.e. basic authentication) for clients accessing Outlook Web Services beginning in October of 2020.  I've been testing Outlook on Android and there are currently many issues regarding 2-way, unattended, sync of contact information between Office 365 and Outlook App for Android.  I've reported all of the issues I identified to Outlook App support, and they say they will address them.  I'm also hoping that Android App providers like Samsung Mail App and Google Gmail App will be updated to support Modern Auth.

 

https://techcommunity.microsoft.com/t5/Exchange-Team-Blog/Improving-Security-Together/ba-p/805892

 

 

","body@stringLength":"1145","rawBody":"

 

 

Please be aware that Microsoft has announced that it is going to forbid App passwords (i.e. basic authentication) for clients accessing Outlook Web Services beginning in October of 2020.  I've been testing Outlook on Android and there are currently many issues regarding 2-way, unattended, sync of contact information between Office 365 and Outlook App for Android.  I've reported all of the issues I identified to Outlook App support, and they say they will address them.  I'm also hoping that Android App providers like Samsung Mail App and Google Gmail App will be updated to support Modern Auth.

 

https://techcommunity.microsoft.com/t5/Exchange-Team-Blog/Improving-Security-Together/ba-p/805892

 

 

","author":{"__ref":"User:user:4769"},"isEscalated":null,"postTime":"2019-11-04T15:35:52.581-08:00","parent":{"__ref":"ForumTopicMessage:message:116984"}},"ForumReplyMessage:message:983680":{"__typename":"ForumReplyMessage","id":"message:983680","revisionNum":1,"uid":983680,"depth":2,"hasGivenKudo":false,"subscribed":false,"board":{"__ref":"Forum:board:microsoft-365"},"conversation":{"__ref":"Conversation:conversation:116984"},"subject":"Re: Multi-factor Authentication breaks outlook","readOnly":false,"editFrozen":false,"moderationData":{"__ref":"ModerationData:moderation_data:983680"},"body":"Our issue was mainly with Outlook 2016 client on Windows 10. Long story short, Outlook was communicating to o365 using Modern Auth, but Basic auth. Ran MS SARA which was flicking a switch somewhere in the windows profile which addressed our issue. As far as the outlook app goes. I have pushed a modern Auth Mail Profile to Android and IOS using Itunes without issue.

Doing this the APP is now using the users network pass instead of the APP Password.","body@stringLength":"462","rawBody":"Our issue was mainly with Outlook 2016 client on Windows 10. Long story short, Outlook was communicating to o365 using Modern Auth, but Basic auth. Ran MS SARA which was flicking a switch somewhere in the windows profile which addressed our issue. As far as the outlook app goes. I have pushed a modern Auth Mail Profile to Android and IOS using Itunes without issue.

Doing this the APP is now using the users network pass instead of the APP Password.","author":{"__ref":"User:user:87754"},"isEscalated":null,"postTime":"2019-11-05T06:25:14.434-08:00","parent":{"__ref":"ForumReplyMessage:message:981897"},"customFields":[],"attachments":{"__typename":"AttachmentConnection","edges":[],"pageInfo":{"__typename":"PageInfo","hasNextPage":false,"endCursor":null,"hasPreviousPage":false,"startCursor":null}},"repliesCount":6},"Revision:revision:1205810_5":{"__typename":"Revision","id":"revision:1205810_5","lastEditTime":"2020-03-02T23:35:22.026-08:00"},"QueryVariables:ReplyList:message:1205810:5":{"__typename":"QueryVariables","id":"ReplyList:message:1205810:5","value":{"id":"message:1205810","first":10,"sorts":{"postTime":{"direction":"DESC"}},"repliesFirst":3,"repliesFirstDepthThree":1,"repliesSorts":{"postTime":{"direction":"DESC"}},"useAvatar":true,"useAuthorLogin":true,"useAuthorRank":true,"useBody":true,"useKudosCount":true,"useTimeToRead":false,"useMedia":false,"useReadOnlyIcon":false,"useRepliesCount":true,"useSearchSnippet":false,"useAcceptedSolutionButton":true,"useSolvedBadge":false,"useAttachments":false,"attachmentsFirst":5,"useTags":false,"useNodeAncestors":false,"useUserHoverCard":false,"useNodeHoverCard":false,"useModerationStatus":true,"usePreviewSubjectModal":false,"useMessageStatus":true}},"ROOT_MUTATION":{"__typename":"Mutation"},"CachedAsset:text:en_US-shared/client/components/users/UserAvatar-1737115705000":{"__typename":"CachedAsset","id":"text:en_US-shared/client/components/users/UserAvatar-1737115705000","value":{"altText":"{login}'s 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Multi-factor Authentication breaks outlook","moderationData":{"__ref":"ModerationData:moderation_data:2927625"},"body":"

Steve_Osuch This was the solution! After this step. I still had to go through the Admin Web Portal>Users>Active Users> click a user then go to \"manage multifactor authentication\". I had to enable the users through that page as well. After your step and the one I mentioned, I am good to go! My tenant is pre 2017 as well, so your solution was correct in that we didn't have MFA enabled by default.

 


 

Solution... force all users to Modern Authentication. In retrospect this makes sense as I've noticed new users always got the modern auth prompt even before trying to implement MFA while the old timers like myself had basic auth prompts still pop up occasionally.

 

Note: this assumes you are on 2016/Outlook for Office 365, 2013 users still additionally have to enable ADAL with registry changes first, then you follow the instructions below to enable modern auth with Exchange Online-> https://support.office.com/en-us/article/enable-modern-authentication-for-office-2013-on-windows-devices-7dc1c01a-090f-4971-9677-f1b192d6c910

 

Solution in detail:

 

Run Powershell - here is another gotcha, in a fun Microsoft twist of irony if you have MFA enabled for this user you will have to download the Microsoft Exchange Online Remote Powershell Module to get modern auth in the powershell environment.  If your username can log in with basic auth, search->powershell->run as admin.

 

Connect to Exchange Online in PowerShell

Connect-EXOPSSession -UserPrincipalName chris@contoso.com   

(for US based Office 365 - for others, you will need to find the URIs)

 

Enable Modern Authentication in Exchange Online

Set-OrganizationConfig -OAuth2ClientProfileEnabled $true  

 

Check Status of Modern Authentication

Get-OrganizationConfig | Format-Table Name,OAuth* -Auto

 

PS C:\\Users\\StevenOsuch> Set-OrganizationConfig -OAuth2ClientProfileEnabled $true
PS C:\\Users\\StevenOsuch> Get-OrganizationConfig | Format-Table Name,OAuth* -Auto

              Name                                        OAuth2ClientProfileEnabled
                ----                                               --------------------------
domain.somewhere.com                                            True

 

 

Now open up Outlook, it worked instantly, I didn't even have to provide credentials as it pulled it from my laptop which already had the SSO profile that had been authenticated at login.

 

Retrospectively, looking at the Set-Up MFA for O365 article (https://docs.microsoft.com/en-us/microsoft-365/admin/security-and-compliance/set-up-multi-factor-authentication?view=o365-worldwide), it mentions this as well but this was just updated a couple of days ago so maybe it wasn't there before.

 

Final note, if you still use Skype for Business, you have to enable Modern Auth separately using the Skype specific connection and command prompts.

 


 

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I'm adding my discovery for anyone currently having the same issue; Microsoft 365, MFA, Business account. Having read through tons of the same issue and trying to solve myself, I was able to connect some dots. The issue is that Modern Authentication is not enabled for the domain.  When you log into M365 as admin, go to Settings tile, Org Settings, scroll to Modern Authentication and turn it on. This corrected the password loop in Outlook, as well as downloading Offline Address Book, and other Outlook oddities after turning on MFA. Hopefully this helps others.

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RobIONDenver 

 

Our Org is set to modern authentication. When coming across users with password loops. I have to temporarily turn off their MFA and reset all MFA Factors, then change password, log them in to Outlook/Onedrive Sync/Word /Teams. THEN, once logged in, I work with the user to enter MFA Factors and THEN I re- enforce MFA on the user. It has been the only way to fix this for us. 

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