An associate of mine ran into this issue recently, and discovered that attempting to deploy Office 365 ProPlus with System Center Configuration Manager, by following this Microsoft article doesn’t work.

NOTE: This post is also available in video format!

Let’s start with getting the install files, etc. prepared and ready for this example.

Prepare O365 Install Files

Per the TechNet article, we need to download the Office Deployment Tool, and then use that tool to download the Office 365 ProPlus installation files.

So briefly, this is what I did.

Downloading the Office Deployment Tool should give you a file like: officedeploymenttool_x86_4747-1000.exe.

You will then see a License Terms screen. Select the checkbox, then click Continue.

Next you will be prompted for a location to extract the files to. Provide a directory, then click OK.

After the files have been extracted, you should receive a message stating that the extraction is complete, click OK.

Now that the files are extracted, in the location that you originally specified, you should see 2 files, namely “Configuration.xml“, and “Setup.exe“.

Next open an Administrative command prompt and navigate to the location where the extracted files are. From there, use the following command line: setup.exe /download. This will initiate the download of the O365 installation files in the same directory, in a new folder labelled “Office”.

Now that the files have been downloaded, we need to create an Application in SCCM.

Create SCCM Application for O365

In the Configuration Manager console, choose Software Library > Application Management > Applications.

On the Home tab, in the Create group, choose Create Application.

On the General page of the Create Application Wizard, select Manually specify the application information, and then choose Next.

On the General information page, enter a name for the application, enter any optional information, and then choose Next.

On the Application Catalog page, provide the information that’s appropriate for your environment, and then choose Next.

On the Deployment Types page, choose Next. We’ll add a deployment type later.

On the Summary page, review the settings you’ve chosen, and then choose Next to create the application.

After the application is created, on the Completion page, choose Close.

Create SCCM Deployment Type for O365

An application in Configuration Manager must contain at least one deployment type. The deployment type contains the installation files for a software package as well as rules that specify when and how the software is deployed. For the Office 365 ProPlus application, the deployment type includes the following:

• The path of the shared folder that contains the Office Deployment Tool, your configuration.xml file, and the Office 365 ProPlus installation files that you downloaded from the Internet.
• The command line that gets the Office Deployment Tool to start the installation of Office 365 ProPlus.
• A detection method, which Configuration Manager uses to determine if Office 365 ProPlus is already installed on the user’s computer.

To Create a Deployment Type

In the Configuration Manager console, choose Software Library > Application Management > Applications.

Select the Office 365 ProPlus application, and then on the Home tab, in the Application group, choose Create Deployment Type.

On the General page of the Create Deployment Type Wizard, in the Type list, select Script Installer, and then choose Next.

On the General Information page, enter a name for the deployment type, enter any optional information, and then choose Next.

On the Content page, do the following:

• In the Content location box, enter the network share where you put the Office Deployment Tool, your configuration.xml file, and the Office 365 ProPlus installation files that you downloaded from the Internet.
• In the Installation program box, enter the following text: setup.exe /configure configuration.xml

After you enter this information, choose Next.

On the Detection Method page, choose Add Clause.

In the Detection Rule dialog box, do the following:

• In the Setting Type list, select Registry.
• In the Hive list, select HKEY_LOCAL_MACHINE.
• In the Key box, enter the following text: Software\Microsoft\Windows\CurrentVersion\Uninstall\O365ProPlusRetail – en-us
• Select the Use (Default) registry key value for detection check box.

Important: Here in lays the problem. Notice in the screenshot that there is an exclamation mark (!) beside the Data Type. Unfortunately, the TechNet article does not mention what this needs to be set to. But in their screenshot, it shows as String. The reason for this is because every Registry Key should have a “(Default)” string within it.

After you enter this information, choose OK, and then on the Detection Method page, choose Next.

On the User Experience page, in the Installation behavior list, select Install for system, and then choose Next.

Note: Although it is not mentioned in the TechNet article, the default setting for Logon Requirement is “Only when a user is logged on”. This is not necessarily the setting you may want, depending on your deployment requirements. Just be aware of it.

If you want to specify any requirements or dependencies for the deployment type, choose Next to go through those pages in the wizard. Otherwise, choose Summary.

On the Summary page, review the settings you’ve chosen, choose Next, and then choose Close.

We now need to distribute the Application content in order to test the deployment.

Distribute the O365 Application

After you create the Office 365 ProPlus application and configure its deployment type, the next step is to copy all the files needed by the application to the appropriate distribution points in your Configuration Manager environment.

To Distribute the Application to Distribution Points

In the Configuration Manager console, choose Software Library > Application Management > Applications.

Select the Office 365 ProPlus application, and then on the Home tab, in the Deployment group, choose Distribute Content.

On the General page of the Distribute Content Wizard, choose Next, and then on the Content page, choose Next.

On the Content Destination page, choose Add > Distribution Point, select the appropriate distribution points, and then choose OK. Then, select Next.

On the Summary page, review the settings you’ve chosen, and then choose Next.

On the Confirmation page, check that the content was successfully assigned to the distribution points, and then choose Close.

To monitor the distribution, go to Monitoring > Distribution Status > Content Status.

Select the application, and then view the Completion Statistics.

Deploy the O365 Application

After the files for the Office 365 ProPlus application are copied to the appropriate distribution points, the next step is to deploy the application. When you deploy the application, you specify which computers or users get the application and when.

To Deploy the Application

In the Configuration Manager console, choose Software Library > Application Management > Applications.

Select the Office 365 ProPlus application, and then on the Home tab, in the Deployment group, choose Deploy.

On the General page of the Deploy Software Wizard, choose Browse for the Collection box, and then select which computers or users that you want to deploy Office 365 ProPlus to. After you’ve made your selection, choose OK, and then choose Next.

On the Content page, choose Next because we’ve already specified the distribution points for the application.

On the Deployment Settings page, in the Purpose list, select Required.

If you want to specify a schedule, configure the user experience, or create an alert, choose Next to go through those pages in the wizard. Otherwise, choose Summary.

On the Summary page, review the settings you’ve chosen, and then choose Next.

On the Confirmation page, check that the application was successfully deployed, and then choose Close.

After you deploy the application, a targeted computer becomes aware of the deployed application during the computer’s next client policy polling cycle, which is once every sixty minutes by default. Then, the computer downloads the installation files for the application from a distribution point into the Configuration Manager client cache. The installation of Office 365 ProPlus takes place from the client cache and no additional files are downloaded from the network or from the Internet.

The Detection Method Issue

So here is the issue. If you take a look at the AppEnforce.log file (located in C:\Windows\CCM\Logs\), you will see that the installed completed successfully. But notice that the detection still says “Application not discovered”.

We can confirm that Office 365 has been installed, because we see all the apps in the Start menu.

But, if we look at Software Center, it shows that the installation “Failed”, or it might say “Not Installed”.

But, let’s go look for that Registry entry as was specified by the TechNet article. As we can see, in the HKEY_LOCAL_MACHINE\Software\Microsoft\Windows\CurrentVersion\Uninstall\O365ProPlusRetail – en-us registry key there is a “(Default)” key value.

Hmm, so the software is installed, the registry entry used for the detection method is present, but it’s not identifying that it’s actually there.

The Solution to the Detection Method Issue

So what can we do? Well, we can use any of the other entries from that registry key (i.e. DisplayName, InstallLocation, etc.). But what I found that works is just un-selecting the “(Default)” checkbox in the detection method.

By not having the “Use (Default) registry key value for detection” checkbox selected, updating the deployment content, and initiating the Application Deployment Evaluation Cycle on the end client; the Software Center will properly show that the application is actually installed.

No restart is required at all, which is nice.

So that’s my findings (based on my co-worker’s experience) with Office 365 ProPlus being deployed via System Center Configuration Manager.