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How To Install ADFS 2012 R2 For Office 365–Part 3

How To Install ADFS 2012 R2 For Office 365–Part 3

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Well then, here we are in part three already!  Previously we:

Installed ADFS 2012 R2 For Office 365 in part 1

Installed ADFS 2012 R2 Proxy For Office 365 in Part 2

Now we want to change the Office 365 domain to be a federated domain.  As discussed in part 1, this means that all of the users who authenticate using this domain will become a federated identity and the on-premises ADFS server is responsible for authenticating these requests.


Update 20-8-2014: Added comment for SupportMultipleDomain switch for the Convert-MSOLDomainToFederated cmdlet.


Importance Of ADFS When Office 365 Relies Upon It

Before we discuss the integration of Office with the on-premises ADFS infrastructure, let’s just again be clear on the criticality of ensuring that ADFS is available when the Office 365 domain is set to use ADFS authentication.  For whatever reason if the ADFS infrastructure is unavailable, then Office 365 cannot complete the authentication process and thus users cannot get access to Office 365.  This will cause a service impacting outage that will require resolution from you, not Microsoft’s online services team.

For this reason, unless you really need to leverage ADFS please review the DirSync password synchronisation feature in the recent DirSync builds.

Apologies if I sound pessimistic, but I don’t want to obviate the requirement for ADFS redundancy!


ADFS in Azure

On the topic of ADFS redundancy one option is to also host a portion of your ADFS infrastructure in Azure.  This is a perfect solution if you do not have sufficient capacity in your current datacentre, or your datacentres are located in close proximity of each other and a major incident would take both of them down.

There is a whitepaper published for this exact scenario. Please check this link. The documentation covers three main scenarios to meet the situations discussed above:

  • Scenario 1: All Office 365 SSO integration components deployed on-premises. This is the traditional approach; you deploy directory synchronization and Active Directory Federation Services (AD FS) by using on-premises servers.
  • Scenario 2: All Office 365 SSO integration components deployed in Windows Azure. This is the new, cloud-only approach; you deploy directory synchronization and AD FS in Windows Azure. This eliminates the need to deploy on-premises servers.
  • Scenario 3: Some Office 365 SSO integration components deployed in Windows Azure for disaster recovery. This is the mix of on-premises and cloud-deployed components; you deploy directory synchronization and AD FS, primarily on-premises and add redundant components in Windows Azure for disaster recovery.


This is an example of hosting ADFS in Azure for DR purposes:

Hosting ADFS In Azure For DR Purposes



AD FS is supported for deployment on Azure Virtual Machines, but there are AD FS best practices that require technologies beyond what AD FS offers itself, such as load balancing/high availability.  In addition to this please also consider the pricing for running this IAAS.  Read through the deployment caveats in the ADFS Azure documentation above and also the additional discussion points here.


Updating ADFS

Back to the business at hand – updating Office 365 so that it now uses your on-premises ADFS server!

We will run the below on a domain joined server on the corporate network.  This has the Windows Azure Active Directory PowerShell Module and the Microsoft Online Sign-In Assistance (SIA) installed.  Let’s launch the WAAD PowerShell module.  For reference the remote ADFS server is Tail-CA-STS.TailspinToys.ca.

For other WAAD management tasks, take a peek at Manage Azure AD using Windows PowerShell page.

Using Connect-MsolService let’s connect to our WAAD instance.  Provide a set of global admin credentials:

Connecting to Windows Azure Active Directory

We can see the current status of the domains within this tenant.  the Get-MsolDomain cmdlet will show the domains, and we are interested in the first domain – “Tailspintoys.ca”.

Reviewing Starting Domain Status

Before we can execute the Convert-MsolDomainToFederated cmdlet, we need to also a hook into the local ADFS server (not the ADFS proxy) so that we can configure it.

There is a word of warning here, as chances are that you will see this lovely screen that features copious red text.

Set-MsolADFSContext : The connection to <ServerName> Active Directory Federation Services 2.0 server failed due to invalid credentials.

 Active Directory Federation Services 2.0 server failed due to invalid credentials" style='background-image: none; padding-top: 0px; padding-left: 0px; display: inline; padding-right: 0px; border-width: 0px;' alt='Set-MsolADFSContext : The connection to Active Directory Federation Services 2.0 server failed due to invalid credentials' src='/cfs-file.ashx/__key/communityserver-blogs-components-weblogfiles/00-00-00-91-09-metablogapi/image_5F00_thumb_5F00_62F9607B.png' border='0' />

This is caused by Remote PowerShell not being enabled on the remote  ADFS server.  This is an issue that is present on ADFS 2012 and ADFS 2012 R2 servers amongst others.  Thankfully it is quite easy to fix, by running the below on the ADFS server:


Once Remote PowerShell has been enabled, we can then connect to the ADFS server using the Set-MsolADFSContext cmdlet. Like the other MSOL cmdlets, this one is as unforgiving.  If you forget to explicitly use the required parameters the MSOL cmdlets typically do not prompt like the Exchange cmdlets do.  Because of this I have a habit of always specifying every option and not relying on PowerShell to prompt for required options that were missed. 

Once we have connected to the ADFS server, we use the Convert-MsolDomainToFederated cmdlet to convert the Office 365 domain from Managed to Federated.

Set-MsolADFSContext -Computer Tail-CA-STS.tailspintoys.ca

Convert-MsolDomainToFederated -DomainName tailspintoys.ca


Update 20-8-2014:  Andy pointed out in the comment that there is an area of concern to be noted here for customers that have multiple top level domains.  Back with ADFS 2.0 customers with multiple top level UPNs had to deploy separate ADFS instances for each domain suffix.  A rollup was added to assist with this and the SupportMultipleDomain switch.   Please see here for more details if you have multiple sign on domains.


Once converted, we check to see if the change applied:

Converting Domain To Federated

Yes it did!  The domain is now Federated.

The full properties of the domain now look like so:

Viewing All Details Of Converted Domain

Please be aware that it can take up to two hours for domain authentication changes to apply.  Go drink a vat of coffee or play some flappy birds!


Testing Access To Office 365 OWA

To test that we are being authenticated to Office 365 OWA via ADFS, let’s see what happens now that the domain has been converted to federated.

Open IE, and navigate to https://outlook.com/tailspintoys.ca  this is the neat shortcut that we can use to access OWA.  Change the domain name to match your own.

When we go to  the browser is redirected to our on-premises ADFS server, at this URL:  https://adfs.tailspintoys.ca/adfs/ls/?wa=wsignin1.0&wtrealm=urn:federation:MicrosoftOnline&wctx=wa%3Dwsignin1.0%26rpsnv%3D3%26ct%3D1398824668%26rver%3D6.1.6206.0%26wp%3DMBI_KEY%26wreply%3Dhttps:%252F%252Fwww.outlook.com%252Fowa%252F%26id%3D260563%26whr%3Dtailspintoys.ca%26CBCXT%3Dout


We then sign in to the on-premises ADFS server:

To On-Premises ADFS Server

ADFS authenticates us, assuming that the password is not fat-fingered, and this authorises Office 365 to let us access OWA:

Signed In To OWA - What A Glorious Sight -- No EMAIL !!

The astute reader will notice that IE in-private mode has been used.  This keeps my testing separate from the other IE Instances running on my laptop.

One thing to note, when testing this connectivity please do so on a regular client machine that has the proper access to the Internet and where the browser is not totally locked down.  In the below example on a Server 2008 R2 SP1 server, when browsing to outlook.com/tailspintoys.ca the user experience is very different from the screenshots above.

ADFS Redirection Experience When Testing On A Server

The user will get logged on, but it can be disconcerting if you are expecting the sexy looking ADFS screen and you get an auth prompt instead…..

ADFS Redirection Experience When Testing On A Server


Testing Office 365 SSO

Chances are you will have use the TestExchangeConnectivity.com site to test and troubleshoot on-premises issues.  The tool has been expanded as now we can also use it to test and diagnose Office 365 issues.

Office 365 Test Connectivity Website

KB 2650717  How to diagnose single sign-on (SSO) logon issues in Office 365 by using Remote Connectivity Analyzer  discusses using the tool to validate SSO.

BONUS TIP – if you get tired of typing that long URL to get to the site, try http://exrca.com


Viewing the SSO Shuffle

Using the IE developer tools, that are accessible by pressing F12 we can see the traffic flow that the browser has taken to reach the sites involved.  You will want to click to enlarge the below.

using IE Developer Tools To View SSO Traffic Flow

Note that we went to the following URLs.  Can you work out why there are three outlook.com ones at the top?



Repairing Office 365 Federated Domain

As discussed in KB 2647048, there are situations that will require the Office 365 domain federation to be repaired.

  • 2523494 (You receive a certificate warning from AD FS when you try to sign in to Office 365, Windows Azure, or Windows Intune
  • 2618887 Error when you try to configure a second federated domain in Office 365: "Federation service identifier specified in the AD FS server is already in use."
  • 2713898 "There was a problem accessing the site" error from AD FS when a federated user signs in to Office 365, Windows Azure, or Windows Intune 
  • 2647020 "Your organization could not sign you in to this service" error and "80041317" or "80043431" error code when a federated user tries to sign in to Office 365
  • 2707348 "Metadata Exchange (MEX) document received from AD FS contains an unknown WS-Trust version" error after you run the MOSDAL Support Toolkit
  • The Federation Service name in AD FS is changed. For more info, go to the following Microsoft website: AD FS 2.0: How to Change the Federation Service Name

For example, you may find yourself running this:

Updating MSOL Federated Domain


Additional Reading

I love this KB as it links to so many other articles that are relevant and introduce many of the issues that can arise with an ADFS deployment.

KB 2647048 -- How to update or to repair the configuration of the Office 365 federated domain 

The PFE Platform blog have some great ADFS content, amongst other things.  Just don't propose to Charity via the comment system please!

How to Build Your ADFS Lab on Server 2012 Part 1

Introduction to Active Directory Federation Services (AD FS) AlternateLoginID Feature

Upgrading ADFS to Server 2012 R2

FAQ on ADFS - Part 1

Finally the TechNet Wiki has the ADFS content section.

ADFS Content MAP




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  • Thanks a lot
    very helpfull

  • Thanks for the Great post Rhod, Excellent walkthrough ... :)

  • I am really glad you wrote this article. I have to implement ADFS for office 365 in the next few months.

  • Thanks for the feedback guys!

    Brad - do let us know how you get on with the deployment!!

    I also have another post coming up that you will love - please subscribe to the RSS feed. I'll probably publish it on Monday.


  • Great work one of the best worked articles I have ever read. One question is around firewall rules for the internal ADFS to the DMZ WAP is only port 443 required between the two servers? Is this bidirectional or one way only?

    Thank again

  • Good question Techno :)

    The firewall stuff is in here http://technet.microsoft.com/en-us/library/dn383648.aspx

    But does not state the direction. I'll see what I can locate....


  • Hi Rhoderick, my users were able to login to the Office 365 ADFS 2.0 with username (ABC)and password without using (FQDN) abc@xyz.com. However, when I upgraded my ADFS farm to Windows Server 2012 R2, the Office 365 ADFS 3.0 login page does not allow users to use username login (abc) rather it ask to enter abc@xyz.com or domain\username.
    How can i fix this issue ?

  • As far as the user experience, what happens if they already have the same password in outlook for Office 365 as AD? Immediately after federated, will they be prompted for their password through outlook? Or will outlook continue to login without prompt?

    This would happen if already using dir sync with password sync enabled and adding ADFS.

  • Outstanding how to article!!! Allows anyone with decent skills to install and understand.

  • thanks

  • Thank you! Very helpful blog! Tell me please if SSO should work during autoiscover (when outlook is adding profile), because this is only place where I am asked for password?

  • Mark and Andrej - Outlook is trying to do basic auth. So this will present the password prompt, which is the reason for the recommendation to save credentials else users get bored of the enter password game....

    As long as the right creds are saved in there it should not prompt, but I'm just back from 3 weeks of holiday and brain is still warning up....


  • Puneet - Not something I've looked at since I always use the user@contoso.com for all auth purposes.


  • Used this awesome guide a few times when installing ADFS/WAP, to ensure I don't miss anything - can I suggest that you point out the -SupportMultipleDomain parameter of the Convert-MSOLDomainToFederated cmdlet, as not specifying this when converting can be a pain to undo.

  • Good point - I'll add a wee note to that Andy!


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