PLEASE NOTE: This is NO LONGER supported and provided as-is for information ONLY. The information here relates to pre-Hybrid configurations that used the Consumer MFG. It does give you some background as to how Office 365 does Federation, though some steps have changed. For a modern “under the hood”, see this article.

As organizations move to make use of cloud based services, like Exchange Online or Outlook Live, it’s pretty important to be able to integrate both the on-premises service and the cloud service so that end-users can continue to work as normal. That’s especially important with a service like Outlook Live, aimed at Education institutions, where typically staff, faculty and some students will continue to be hosted on-premise and the majority of students will be hosted in the cloud. A seamless experience makes life easier for users and thus easier for IT…

So, with Outlook Live and Exchange 2010 On-Premises there is a pretty good opportunity to get Exchange working seamlessly between both systems. I’ll be covering a unified login in a further article (once I’ve re-written the code we use in-house into a re-distributable form). But for now, I’m focusing on the user experience with free/busy and calendar sharing.

One of the areas users might expect to “just work” is free/busy and calendar sharing between on-premise and cloud. The options are there, it looks like it tries to do it.. But the end user just gets unfriendly error messages and “permission denied” errors. To get this up and running in Exchange 2010 SP1 is actually now pretty simple. Although SP1 allows self-signed certificates for Federation, you cannot use these with Outlook Live federation, and you’ll need to perform an extra step. However it’s still fairly straightforward…

Pre-requisites

First things first, we need a few things in-place and working already before we can get going. The main pre-req is Autodiscover, but I won’t cover how to set this up, as it’s is covered in detail elsewhere on the good old ‘net..

• Autodiscover working for On-Premises for the domain you want to use (using DNS names, not a service records)
• Autodiscover working for Outlook Live for the domain you want to use (again, using DNS names, not a service record)
• Separate domains for on-premises and Outlook Live (I’m testing getting shared working – follow up article to come)
• Exchange 2010 CAS Connectivity to *.outlook.com
• Org admin rights on Exchange 2010 SP1 and Tenant Admin rights on Outlook Live, along with Powershell access to both.
• Access to manage the DNS for both domains and add TXT records.
• External URL setup and tested for Exchange Web Services / WebServicesVirtualDirectory

Once that’s all setup and available, you should be ready to go..

Setting it up

To keep things simple, we’re not going to do anything too complicated, we’re going to set things up so all users in both on-premises and Outlook Live can see each other’s free/busy and share calendars (and contacts). Also, for the purposes of this article it’s assumed no Sharing Policy is setup already.

On our test setup, we’ve got two domains:

On Premises: rootuk.net
Outlook Live: test.rootuk.net

Basically we need to create four things on-premise:

• A Federation Trust to authenticate us against the MS Federation Gateway
• A new sub-domain ExchangeDelegation for the account namespace (in this example, ExchangeDelegation.rootuk.net)
• An Organization Relationship to say Outlook Live can see in for Free busy
• Finally a Sharing Policy to allow on-premise users to share their calendars with Outlook Live users.

In Outlook Live the trust with MS’s Federation Gateway is there by default so we just need the Organization Relationship to allow On-premise to see in and the Sharing Policy to allow the Outlook Live users to share with On-premise users.

First, we’ll setup the on-premise config, then get the Outlook Live stuff done. Afterwards we’ll test everything works.

On Premises Config

Step One – Setup a New Federation Trust using a trusted certificate [Updated 10th Nov 2010]

To setup a Federation Trust for use with Outlook Live, you need to use a certificate from an approved certificate authority. As this list is quite short, you may find it doesn’t include you current SAN/UCC certificate provider (for example, if you use the JANET Certificate Service), however this isn’t a major issue. The certificate you use for Federation doesn’t have to be the same one you currently use for your other Exchange services, so fear not – you don’t need to buy a new, expensive SAN/UCC certificate. I’ve found the cheapest one from GoDaddy works just fine.

If you’ve already got a supported certificate, you can skip this part and just use your existing certificate thumbprint for the New-FederationTrust command. Otherwise, to generate a new request for a single domain certificate just to use for Federation, use New-ExchangeCertificate:

Next, follow the standard process for your CA, by requesting, then downloading the certificate from the third party certificate provider:

After downloading the certificate, you now need to complete the certificate request by importing the certificate into Exchange:

Note down the Thumbprint in the output, and then create the Federation Trust using that thumbprint value. Note that we’re choosing the “Legacy Provisioning Service” as part of this process. This is why we can’t use a self-signed request – these only work against a new “Business” gateway. Outlook Live currently works against a legacy “Consumer” gateway and the -UseLegacyProvisioningService parameter switches us to use that one.

NB.. You’ll see in that example above I got an error the first time. This does happen occasionally and I’ve seen it reported in forums too. The error is “The request failed with HTTP status 403: Forbidden”. Just retrying the command should work.

Next, we need to setup a record in DNS for the application ID using the ExchangeDelegation sub-domain and the main On-Premises domain we wish to use for federation. As of SP1, it’s possible to use the “Federated Domain Proof” DNS TXT record, but as we’re using the legacy method, we will use the Application ID method.

To add the App ID, you need to add a DNS record that contains your Application ID (shown as “ApplicationIdentifier” in the output from “New-FederationTrust”, or by entering “Get-FederationTrust”) and enter it in the form “AppID=”.

If you use Windows DNS, it goes a little something like this:

Once those are both in, reload/HUP your DNS and make sure you can resolve it, both from your Exchange servers and from the outside world. The following command should work:

Now we’ve got the Federated Trust and DNS record sorted, we can get ourselves properly setup with the Federated Gateway. To do this, we first need to add the accepted domain of the Federated namespace:

Next, we first use the Set-FederatedOrganizationIdentifier command to configure the account namespace:

Finally, add the main domain name of the On Premises domain:

Assuming that completes successfully, we can move onto the next step..

Step Two– Setup the On-Premise Organization Relationship

The next step is to allow our Outlook Live domain to see our On-premise Free/Busy info. You can do this via Powershell or the Exchange Management Console:

Via Powershell:

Test that you can get the federation info for your Outlook Live domain. If you get an error, run the command again with the -Verbose parameter for a detailed error and check your autodiscover setup for Outlook Live:

Next, configure the relationship. The LimitedDetails option below is the most open setting for the relationship, which means any user who has chosen to show that much detail will also make it available to the Outlook Live tenant.

If you’d rather configure via Exchange Management Console:

Navigate to Organization Configuration, and select the Organization Relationships Tab. Right click in the whitespace and choose “New Organization Relationship”:

in the New Organization Relationship window, Give a the new relationship a friendly name (e.g. Outlook Live). Select the checkbok “Enable this organization relationship”, then choose to enable free/busy access. Choose “Free/busy access with time, plus subject and location” to select the widest access. This means any user who has chosen to show that much detail (i.e. people can see that on-premise right now) will also share it to Outlook Live.

Next enter the Outlook Live domain in the Automatically discover configuration information text box, and press Next.

Check for any errors, and press Finish. If there are errors, and it isn’t a typo, then it’s likely to be an Autodiscover issue – but you’ll find out most detail on the possible cause if you use the Powershell instructions above.

The new relationship should now be listed underneath Organization Relationships:

Step 3 – Setup the Sharing Policy

To enable our on-premise users to share their information with Outlook Live users we need a sharing policy setup. While you can setup multiple sharing policies and assign them to different users, for this basic sharing we’re going to modify the default sharing policy

Via Powershell:

First, check your settings. Note down the existing Domains value.

Replace the domains value on the Default Sharing Policy setting the original value (or remove it, if you want) and adding the Outlook Live domain. For the Outlook Live domain we’re setting the maximum scope for sharing:

If you’d prefer to configure the sharing policy via the Exchange Management Console:

Navigate to Organization Configuration > Mailbox > Sharing Policies, then right click the Default Sharing Policy, then choose Properties:

In the Default Sharing Policy Properties, choose “Add”, then specify the Outlook Live domain. To allow for the maxium level of detail to be shared by individual users, select the last option “Calendar sharing with free/busy information plus subject, location and body, Contacts sharing:

And that’s it for On-Premise. Next.. We need to get the hosted environment setup with with the corresponding parameters:

Outlook Live Setup

For the Outlook Live setup you have to use Powershell – Exchange Management Shell isn’t supported when managing your hosted tenant. If you’re not sure how to connect Powershell see the guide on the Outlook.com help site, but it basically looks a little like this:

Step 1: Setup the Outlook Live Organization Relationship

We get to miss out the first step that we had to do on-premise, setup of the federation trust, because as a tenant of the outlook.com Exchange environment this has already in place.. So we can skip to getting an organization relationship setup with our on-premise domain.

First, we check that we can indeed discover the correct settings by using the Get-FederationInformation command, specifying the on-premise domain:

The output from the command should show details matching the Organization Identifier and Application URI we setup earlier, along with the details of the on-premise Autodiscover environment.

If it returns a failure you may need to double check your Autodiscover settings for the on-premise environment, or in some cases you may need to give it a little while (if you just setup your Federation Trust on-premise) and try again. For example, in my production environment it took around an hour for my production Outlook Live tenant to be able to discover the Federation Information although my test domains could see the same information without any issues.

So.. After you’ve tested Outlook Live can discover the Federation Information, it’s onto actually creating the Organization Relationship. The command is exactly the same as on-premise,we are really just swapping the domain:

Step 2: Setup the sharing policy

Finally, it’s on to the final step – getting the sharing policy sorted. Check out what the Default Sharing Policy currently is before we go and add our on-premise domain:

Then replace the Domains list for the Default Sharing Policy with a value that includes the on-premise domain. In the example below, I’m keeping the settings that were already there and adding the on-premise domain. For consistency, I’m also keeping the same sharing level as set on-premise:

After that, it should all be done. Give it a little bit of time (say, 15 minutes) for everything to take effect and we should be ready to have a play..

Testing it out

For testing purposes on my two domains, on-premise “rootuk.net” and Outlook Live “test.rootuk.net”, I’ve created test accounts in each –“onpremise@rootuk.net” and “outlooklive@test.rootuk.net”. For the screenshots I’ve used OWA, but it works equally well in Outlook.

The first test is for Free/Busy. I’ve created a few test appointments in both calendars and you’ll see availability works just as if the user was on-premise:

In Outlook Live, scheduling a new meeting with the on-premise user as an attendee:

Next, via on-premise Exchange 2010 SP1, with our Outlook Live user as an attendee this time:

The second test is to check it is possible to share a calendar either way, and this is where it strays slightly away from the full range of options available to users within a single environment.

The limitations we’ve got mean that the user must share the calendar using OWA or Outlook 2010, and must use the “share this calendar” options rather than setting permissions directly. The recipient of the permission must add the calendar using the resulting email (they can’t just add it by name) and it’s read-only. this of course means the process can’t be easily automated, but it does allow users to use a common workflow to share folders, via the “share” options.

Sharing a calendar in Outlook Live:

On-premise user receives the sharing invitation and chooses “Add this calendar” to add it:

After adding the calendar, it’s shown in red (in OWA, anyway) while the server retrieves the calendar:

After a minute or so, the Outlook Live calendar shows up alongside the On-premise calendar:

Finally, let’s test it from On-premise to Outlook Live:

Select the Calendar’s “Share” option to share the calendar (it’s worth noting that the OWA UI has changed between RTM and SP1.. but I digress):

Over in Outlook Live, the Outlook Live user receives the invitation and again, chooses the “Add this calendar” link:

After choosing to add the calendar, the on-premise calendar shows (again after a minute or so to do the first sync) alongside the Outlook Live calendar:

Contacts sharing is again a similar process, although it must be shared using Outlook 2010. Simply right click a contacts folder and choose Share>Share Contacts:

And that’s it – hopefully this will work for you, but if you have any questions or any issues, just use the comments form below.

Update – 10th November 2010: The original article used the -MetaDataURL parameter to use a self-signed certificate with the old “consumer” gateway. This is no longer valid. The article has been updated to reflect the new process, which requires an acceptable third-party certificate and the -LegacyProvisioningService parameter. If you have used the -MetaDataURL parameter to setup Federated Sharing you should remove and re-create both the organizational relationship (both sides) and the federation trust (on premises) using the updated information in “Step 1” of the On Premises Config. You do not need to remove/re-create the sharing policy.

Update – 15th December 2010: The article has been updated to use ExchangeDelegation.domain.com for the Federated Namespace based on advise from the Exchange team. This is a best practise and pre-req for cross-premises Free/Busy.