AD FS Single Sign On - only working for 1 user


I have set up SSO for use with office 365 and Dropbox.

When I was testing both Office 365 and Dropbox with my domain account it was working fine.

for Office 365 I would go to and enter my work email address.

I would get re-directed to and I would enter my domain password and I would be logged into office 365.

I assumed all was fine so I allocated licenses to my 20 users in office 365 but when they went to sign in at and were re-directed to - entered their correct password - the page would just submit back to itself.

if the user entered the wrong domain password at then it would give the error that the password is wrong. When the password was correct it would just post back to itself with no error message.

I cannot work out why this is happening.

any help would be appreciated.


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jackbensonAuthor Commented:
All the users are added to Office 365 by DirSync so all I had to do was activate the Office 365 license

office 365 portal - showing Active Directory Synchronisation
Vasil Michev (MVP)Commented:
They dont need license to login, but the ImmutableID and UPN needs to be properly configured (matching the on-prem value). Subdomains are treated differently/require additional configuration. So double-check on those. You can also try recreating the RPT as detailed here:

If this doesnt help, capture the outgoing SAML token via Fiddler or similar tool end examine the content. Detailed steps can be found here:
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jackbensonAuthor Commented:

I have made some progress.

I have found the option "Edit Global Authentication Policy" in "Primary Authentication" in "Authentication Policy" in the AD FS Management Console

AD FS Primary Authenication - Edit Global Authentication Policy
after I have enabled the "Forms Authentication" option in the Intranet section users within the company network could go to, enter their UPN and the following pops up:

Single Sign On Screen - withing company network
the user could then enter the network credentials and then be logged into office 365 - good result :)

But when a user that is not in the internal network (I do not know if this is just to do with the computer in the office being part of the domain) and the user goes to, enters their email addess the following pops up:

Single Sign On Screen - outside of company network
and this is the details of the Token Signing Public Key Certificate:

Token Signing Public Key Certificate
I assume this is not how is it supposed to work?

can you suggest how to fix it

many thanks

Vasil Michev (MVP)Commented:
Seems like you have configured a second-factor auth for external users? You cannot use certificate-based auth with O365.
jackbensonAuthor Commented:
In "Edit Global Authentication Policy" I have not selected "Certificate Authentication" in either Extranet or Intranet options.

is there somewhere else I should look to disable the certificate authentication?
Vasil Michev (MVP)Commented:
Those settings can also be configured on per RPT, so check (or just do a Get-AdfsRelyingPartyTrust | fl AdditionalAuthenticationRules).

This might also be pre-auth done on the proxy level. What are you using for the AD FS proxies, any TMGs or Netscaler, etc?
jackbensonAuthor Commented:

this is my result from the above command:

PS C:\Windows\system32> Get-AdfsRelyingPartyTrust | fl AdditionalAuthenticationR
AdditionalAuthenticationRules :
AdditionalAuthenticationRules :
AdditionalAuthenticationRules :
PS C:\Windows\system32>

For the proxy I am using the "Web Application Proxy" in Server 2012 R2 - a VM that is not joined to the domain.

Web Application Proxy
I was trying to look at the setting for this - but for the life of me I cannot find an option to see the setting of how I set it up

Vasil Michev (MVP)Commented:
OK so you dont seem to have any additional auth rules, so it leaves with the proxies (or some other device between the local AD FS server and the internet). For the WAP, do you remember how you published the AD FS rule? You can do a quick check if any pre-auth is set using this cmdlet:

Get-WebApplicationProxyApplication | fl Name,ExternalPreAuthentication
jackbensonAuthor Commented:
I ran: Get-WebApplicationProxyApplication | fl Name,ExternalPreAuthentication on the Web Application Proxy and it did not return any information
Vasil Michev (MVP)Commented:
OK, so doesnt seem to be there as well. Any other devices between the Internet and the AD FS server that might be doing pre-auth?

Go to and run the Office 365 Single Sign-On Test under the O365 tab. Post back the sanitized results here.
jackbensonAuthor Commented:

I had tried this before and there is no problem.


this morning I tested a Windows computer that is on the internal company lan - but not joined to the domain - and after entering the email address at I was prompted for the domain username/password (in a dialogue box) and was able to log into office 365.

I also tried on a Mac that is joined to the domain - but I was not prompted for the username/password in a dialogue box and was not able to log into office 365

I appreciate your help

Vasil Michev (MVP)Commented:
OK, so if it's only on Mac, the issue is definitely not with any pre-auth settings or MFA as I though initially. There were some issues with Mac/iOS devices and AD FS 2.0, not sure if those apply to AD FS 3.0 though...

One thing that is known to cause issues with non-MS browsers is Extended Protection for Authentication (EPA) - check if it's enabled and temporary disable it. You can refer to method 3 in this article:
jackbensonAuthor Commented:
I should do this on the AD FS server? not the "Web Application Proxy" Server?

I did not think AD FS on Server 2012 R2 used IIS?


Vasil Michev (MVP)Commented:
Use the PowerShell cmdlet:

Set-ADFSProperties –ExtendedProtectionTokenCheck None

Open in new window

jackbensonAuthor Commented:

I did this and I am still unable to log into to single sign-on in the following situation:

- Within Company Network - Apple Macs
- Outside of the Company Network - Any computer.

within the company network, on a PC, I am prompted for the username / password in a dialogue box.

I have resolved the issue of behind asked to select a certificate while singing in - I disabled "Enable Device Authentication" in  "Edit Global Authentication Policy" in "Primary Authentication" in "Authentication Policy"

I do not know if this is useful, but these are my ADFS properties:

PS C:\Windows\system32> get-ADFSProperties

AcceptableIdentifiers                      : {}
AddProxyAuthorizationRules                 : exists([Type == "http://schemas.mi
                                             aims/groupsid", Value ==
                                             "S-1-5-32-544", Issuer =~ "^AD
                                             AUTHORITY$"]) => issue(Type = "htt
                                             ation/claims/permit", Value =
                                                         c:[Type == "http://sch
                                             tity/claims/primarysid", Issuer
                                             =~ "^AD AUTHORITY$" ]
                                                                    => issue(st
                                             param=c.Value );
                                                         c:[Type == "http://sch
                                             tity/claims/proxytrustid", Issuer
                                             =~ "^SELF AUTHORITY$" ]
                                                                    => issue(st
                                             param=c.Value );
ArtifactDbConnection                       : Data
                                             Source=SQLSERVER2\ADFS;Initial Cat
                                             Security=True;Min Pool Size=20
AuthenticationContextOrder                 : {urn:oasis:names:tc:SAML:2.0:ac:cl
                                             asses:Password, urn:oasis:names:tc
                                             ctedTransport, urn:oasis:names:tc:
                                             SAML:2.0:ac:classes:TLSClient, urn
AutoCertificateRollover                    : True
CertificateCriticalThreshold               : 2
CertificateDuration                        : 365
CertificateGenerationThreshold             : 20
CertificatePromotionThreshold              : 5
CertificateRolloverInterval                : 720
CertificateSharingContainer                : CN=6fbeafbf-74ff-4c01-ad64-0446fba
                                             ram Data,DC=DomainName,DC=local
CertificateThresholdMultiplier             : 1440
ClientCertRevocationCheck                  : None
ContactPerson                              : Microsoft.IdentityServer.Managemen
DisplayName                                : Company Name
IntranetUseLocalClaimsProvider             : False
ExtendedProtectionTokenCheck               : None
FederationPassiveAddress                   : /adfs/ls/
HostName                                   :
HttpPort                                   : 80
HttpsPort                                  : 443
TlsClientPort                              : 49443
Identifier                                 :
InstalledLanguage                          : en-US
LogLevel                                   : {Errors, Information, Verbose,
MonitoringInterval                         : 1440
NetTcpPort                                 : 1501
NtlmOnlySupportedClientAtProxy             : True
OrganizationInfo                           :
PreventTokenReplays                        : True
ProxyTrustTokenLifetime                    : 21600
ReplayCacheExpirationInterval              : 60
SignedSamlRequestsRequired                 : False
SamlMessageDeliveryWindow                  : 5
SignSamlAuthnRequests                      : False
SsoLifetime                                : 480
PersistentSsoLifetimeMins                  : 10080
KmsiLifetimeMins                           : 1440
PersistentSsoEnabled                       : True
PersistentSsoCutoffTime                    : 01/01/0001 00:00:00
KmsiEnabled                                : False
LoopDetectionEnabled                       : True
LoopDetectionTimeIntervalInSeconds         : 20
LoopDetectionMaximumTokensIssuedInInterval : 5
PasswordValidationDelayInMinutes           : 60
SendClientRequestIdAsQueryStringParameter  : False
WIASupportedUserAgents                     : {MSAuthHost/1.0/In-Domain, MSIE
                                             6.0, MSIE 7.0, MSIE 8.0...}
ExtranetLockoutThreshold                   : 2147483647
ExtranetLockoutEnabled                     : False
ExtranetObservationWindow                  : 00:30:00

PS C:\Windows\system32>

PS C:\Windows\system32> Get-ADFSProperties | Select  -ExpandProperty WIASupporte
MSIE 6.0
MSIE 7.0
MSIE 8.0
MSIE 9.0
MSIE 10.0
Windows Rights Management Client
PS C:\Windows\system32>
jackbensonAuthor Commented:
I also ran this command to add different browser support:

Set-ADFSProperties -WIASupportedUserAgents @("MSIE 6.0", "MSIE 7.0", "MSIE 8.0", "MSIE 9.0", "MSIE 10.0", "Trident/7.0", "MSIPC", "Windows Rights Management Client", "Mozilla/5.0", "Safari/6.0", "Safari/7.0", "Safari/8.0")

On the mac I have been able to activate office with the 1 user account that was working at the start.
Vasil Michev (MVP)Commented:
If you mean true seamless SSO experience, this is only possible for domain joined machines. To enable it, make sure Windows Authentication is selected in the global auth policy, that the AD FS FQDN is added to Local sites in IE settings and WIA is enabled for the zone. The behavior and requirements for both inside and outside the corp network are explained in details here:
jackbensonAuthor Commented:
I found this article which described a similar issue to what I am experiencing in that only administrators could log into from outside my company network:

one user wrote:

"update on this issue. I figured out what was causing this. I use a managed service account for the ADFS service, because this is best practice.

It looks like the Managed Service account has too less permission to read the user properties to let them authenticate. When I add the managed service account and give it read permission to a user that didn't work I can logon successfully. I can of course add this right to the whole OU where the users are in to fix it for all users.

Is this a security issue? Give i now to less or too much security too this account. Can someone give me advise what permissions to give.


so I added read permission for the Managed Service Account DomainName\ADFS2SVC to a user that could not log into externally - and that user was then able to log in.

Does it surprise you to read this?

what is best practice for giving permissions to the DomainName\ADFS2SVC?

Another thing suggested in the article is to add the Managed Service Account DomainName\ADFS2SVC to the Windows Authorization Access Group

your thoughts would be appreciated

many thanks

Vasil Michev (MVP)Commented:
Nice catch, definitely havent seen this one before. Not sure why "Authenticated Users" was missing from the "Pre-Windows 2000 Compatible Access" group in their case, it's present on all the ADs I manage. But check for that, and fix it if needed. Same for the "Windows Authorization Access" group and the gmsa.
jackbensonAuthor Commented:

thank-you for your reply.

to confirm my understanding, am I to add the Managed Service Account DomainName\ADFS2SVC to both the following Security Groups:
- Pre-Windows 2000 Compatible Access
- Windows Authorization Access

Windows Authorization Access Group Windows Authorization Access Group-
at the moment it is not in either

or am I supposed to add Authenticated Users to these groups?

many thanks

Vasil Michev (MVP)Commented:
Start by adding "Authenticated Users" to the "Pre-Windows 2000 Compatible Access" group. It should take care of the lack of read access. Not sure why it was removed in the first place.

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jackbensonAuthor Commented:
and I can ignore the Windows Authorization Access group?
Vasil Michev (MVP)Commented:
Well it might not be needed. As I said, I havent actually encountered this issue before, so I cannot speak from experience. My idea is - take it one step at a time, as however small those actions are they do introduce changes in the environment, so avoid doing changes you dont really need.
jackbensonAuthor Commented:

it looks like just adding "Authenticated Users" to the "Pre-Windows 2000 Compatible Access" was enough to let people log in

thank-you for your help!

jackbensonAuthor Commented:
I really appreciate your help in working through the problem with me and getting to the answer
Vasil Michev (MVP)Commented:
In all fairness, you found the answer :)
jackbensonAuthor Commented:
well.. I had found it before I started writing on this post - but just because it was only somewhere does not mean it was a safe thing to do :)
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Windows Server 2012

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