Double Key Encryption for Microsoft 365
Instructions for: Azure Information Protection unified labeling client for Windows
Service description for: Microsoft 365 Compliance
Double Key Encryption (DKE) uses two keys together to access protected content. Microsoft stores one key in Microsoft Azure, and you hold the other key. You maintain full control of one of your keys using the Double Key Encryption service. You apply protection using The Azure Information Protection unified labeling client to your highly sensitive content.
Double Key Encryption supports both cloud and on-premises deployments. These deployments help to ensure that encrypted data remains opaque wherever you store the protected data.
For more information about the default, cloud-based tenant root keys, see Planning and implementing your Azure Information Protection tenant key.
When your organization should adopt DKE
Double Key Encryption is intended for your most sensitive data that is subject to the strictest protection requirements. DKE is not intended for all data. In general, you'll be using Double Key Encryption to protect only a very small part of your overall data. You should do due diligence in identifying the right data to cover with this solution before you deploy. In some cases, you might need to narrow your scope and make use of other solutions for the majority of your data such as Microsoft Information Protection with Microsoft-managed keys or BYOK. These solutions are sufficient for documents that aren't subject to enhanced protections and regulatory requirements. Also, these solutions enable you to use the most powerful Office 365 services; services that you can't use with DKE encrypted content. For example:
- Transport rules including anti-malware and spam that require visibility into the attachment
- Microsoft Delve
- Content search and indexing
- Office Web Apps including co-authoring functionality
Any external applications or services that are not integrated with DKE through the MIP SDK will be unable to perform actions on the encrypted data.
The Microsoft Information Protection SDK 1.7+ supports Double Key Encryption; applications that integrate with our SDK will be able to reason over this data with sufficient permissions and integrations in place.
We recommend organizations use Microsoft Information protection capabilities (classification and labeling) to protect most of their sensitive data and only use DKE for their mission-critical data. Double Key Encryption is particularly relevant for extremely sensitive data in highly regulated industries such as Financial services and Healthcare.
If your organizations have any of the following requirements, you can use DKE to help secure your content:
- You want to ensure that only you can ever decrypt protected content, under all circumstances.
- You don't want Microsoft to have access to protected data on its own.
- You have regulatory requirements to hold keys within a geographical boundary. All of the keys that you hold for data encryption and decryption are maintained in your data center.
System and licensing requirements for DKE
Double Key Encryption for Microsoft 365 comes with Microsoft 365 E5 and Office 365 E5. If you don’t have a Microsoft 365 E5 license, you can sign up for a trial. For more information about these licenses, see Microsoft 365 licensing guidance for security & compliance.
Azure Information Protection. DKE works with sensitivity labels and requires Azure Information Protection.
DKE sensitivity labels are made available to end-users through the sensitivity ribbon in Office Desktop Apps. Install these prerequisites on each client computer where you want to protect and consume protected documents.
Microsoft Office Apps for enterprise version *.12711 or later (Desktop versions of Word, PowerPoint, and Excel) on Windows.
Azure Information Protection Unified Labeling Client versions 126.96.36.199 or later. Download and install the Unified Labeling client from the Microsoft download center.
Supported environments for storing and viewing DKE-protected content
Supported applications. Microsoft 365 Apps for enterprise clients on Windows, including Word, Excel, and PowerPoint.
Online content support. Documents and files stored online in both Microsoft SharePoint and OneDrive for Business are supported. You can share encrypted content by email, but you can't view encrypted documents and files online. Instead, you must view protected content using the desktop apps on your local computer.
Overview of deploying DKE
You'll follow these general steps to set up DKE. Once you've completed these steps, your end users will be able to protect your highly sensitive data with Double Key Encryption.
Deploy the DKE service as described in this article.
Create a label with Double Key Encryption. Navigate to Information protection under the Microsoft 365 compliance center and create a new label with Double Key Encryption. See Restrict access to content by using sensitivity labels to apply encryption.
Use Double Key Encryption labels. Protect data by selecting the Double Key Encrypted label from the Sensitivity ribbon in Microsoft Office.
There are several ways you can complete some of the steps to deploy Double Key Encryption. This article provides detailed instructions so that less experienced admins successfully deploy the service. If you're comfortable doing so, you can choose to use your own methods.
This article and the deployment video use Azure as the deployment destination for the DKE service. If you're deploying to another location, you'll need to provide your own values.
Watch the Double Key Encryption deployment video to see a step-by-step overview of the concepts in this article. The video takes about 18 minutes to complete.
You'll follow these general steps to set up Double Key Encryption for your organization.
- Install software prerequisites for the DKE service
- Clone the Double Key Encryption GitHub repository
- Modify application settings
- Generate test keys
- Build the project
- Deploy the DKE service and publish the key store
- Validate your deployment
- Register your key store
- Create sensitivity labels using DKE
- Enable DKE in your client
- Migrate protected files from HYOK labels to DKE labels
When you're done, you can encrypt documents and files using DKE. For information, see Apply sensitivity labels to your files and email in Office.
Install software prerequisites for the DKE service
Install these prerequisites on the computer where you want to install the DKE service.
.NET Core 3.1 SDK. Download and install the SDK from Download .NET Core 3.1.
Visual Studio Code. Download Visual Studio Code from https://code.visualstudio.com/. Once installed, run Visual Studio Code and select View > Extensions. Install these extensions.
C# for Visual Studio Code
NuGet Package Manager
Git resources. Download and install one of the following.
OpenSSL You must have OpenSSL installed to generate test keys after you deploy DKE. Make sure you're invoking it correctly from your environment variables path. For example, see "Add the installation directory to PATH" at https://www.osradar.com/install-openssl-windows/ for details.
Clone the DKE GitHub repository
Microsoft supplies the DKE source files in a GitHub repository. You clone the repository to build the project locally for your organization's use. The DKE GitHub repository is located at https://github.com/Azure-Samples/DoubleKeyEncryptionService.
The following instructions are intended for inexperienced git or Visual Studio Code users:
In your browser, go to: https://github.com/Azure-Samples/DoubleKeyEncryptionService.
Towards the right side of the screen, select Code. Your version of the UI might show a Clone or download button. Then, in the dropdown that appears, select the copy icon to copy the URL to your clipboard.
In Visual Studio Code, select View > Command Palette and select Git: Clone. To jump to the option in the list, start typing
git: cloneto filter the entries and then select it from the drop-down. For example:
In the text box, paste the URL that you copied from Git and select Clone from GitHub.
In the Select Folder dialog that appears, browse to and select a location to store the repository. At the prompt, select Open.
The repository opens in Visual Studio Code, and displays the current Git branch at the bottom left. The branch should be master.
Select the word master from the list of branches.
Selecting the master branch ensures that you have the correct files to build the project. If you do not choose the correct branch your deployment will fail.
You now have your DKE source repository set up locally. Next, modify application settings for your organization.
Modify application settings
To deploy the DKE service, you must modify the following types of application settings:
You modify application settings in the appsettings.json file. This file is located in the DoubleKeyEncryptionService repo you cloned locally under DoubleKeyEncryptionService\src\customer-key-store. For example, in Visual Studio Code, you can browse to the file as shown in the following picture.
Key access settings
Choose whether to use email or role authorization. DKE supports only one of these authentication methods at a time.
Email authorization. Allows your organization to authorize access to keys based on email addresses only.
Role authorization. Allows your organization to authorize access to keys based on Active Directory groups, and requires that the web service can query LDAP.
To set key access settings for DKE using email authorization
Open the appsettings.json file and locate the
Add the email address or addresses that you want to authorize. Separate multiple email addresses with double quotes and commas. For example:
"AuthorizedEmailAddress": ["email@example.com", "firstname.lastname@example.org ", "email@example.com"]
LDAPPathsetting and remove the text
If you use role authorization (AuthorizedRoles) then this is the LDAP path.between the double quotes. Leave the double quotes in place. When you're finished, the setting should look like this.
AuthorizedRolessetting and delete the entire line.
This image shows the appsettings.json file correctly formatted for email authorization.
To set key access settings for DKE using role authorization
Open the appsettings.json file and locate the
Add the Active Directory group names you want to authorize. Separate multiple group names with double quotes and commas. For example:
"AuthorizedRoles": ["group1", "group2", "group3"]
LDAPPathsetting and add the Active Directory domain. For example:
AuthorizedEmailAddresssetting and delete the entire line.
This image shows the appsettings.json file correctly formatted for role authorization.
Tenant and key settings
DKE tenant and key settings are located in the appsettings.json file.
To configure tenant and key settings for DKE
Open the appsettings.json file.
ValidIssuerssetting and replace
<tenantid>with your tenant ID. You can locate your tenant ID by going to the Azure portal and viewing the tenant properties. For example:
"ValidIssuers": [ "https://sts.windows.net/9c99431e-b513-44be-a7d9-e7b500002d4b/" ]
<yourhostname> with the hostname of the machine where the DKE service will run. For example:
The value for
JwtAudience must match the name of your host exactly. You may use localhost:5001 while debugging. However, When you're done debugging, make sure to update this value to the server's hostname.
TestKeys:Name. Enter a name for your key. For example:
TestKeys:Id. Create a GUID and enter it as the
TestKeys:IDvalue. For example,
DCE1CC21-FF9B-4424-8FF4-9914BD19A1BE. You can use a site like Online GUID Generator to randomly generate a GUID.
This image shows the correct format for tenant and keys settings in appsettings.json.
LDAPPath is configured for role authorization.
Generate test keys
Once you have your application settings defined, you're ready to generate public and private test keys.
To generate keys:
From the Windows Start menu, run the OpenSSL Command Prompt.
Change to the folder where you want to save the test keys. The files you create by completing the steps in this task are stored in the same folder.
Generate the new test key.
openssl req -x509 -newkey rsa:2048 -keyout key.pem -out cert.pem -days 365
Generate the private key.
openssl rsa -in key.pem -out privkeynopass.pem
Generate the public key.
openssl rsa -in key.pem -pubout > pubkeyonly.pem
In a text editor, open pubkeyonly.pem. Copy all of the content in the pubkeyonly.pem file, except the first and last lines, into the
PublicPemsection of the appsettings.json file.
In a text editor, open privkeynopass.pem. Copy all of the content in the privkeynopass.pem file, except the first and last lines, into the
PrivatePemsection of the appsettings.json file.
Remove all blank spaces and newlines in both the
When you copy this content, do not delete any of the PEM data.
In Visual Studio Code, browse to the Startup.cs file. This file is located in the DoubleKeyEncryptionService repo you cloned locally under DoubleKeyEncryptionService\src\customer-key-store.
Locate the following lines:
#if USE_TEST_KEYS #error !!!!!!!!!!!!!!!!!!!!!! Use of test keys is only supported for testing, DO NOT USE FOR PRODUCTION !!!!!!!!!!!!!!!!!!!!!!!!!!!!! services.AddSingleton<ippw.IKeyStore, ippw.TestKeyStore>(); #endif
- Replace these lines with the following text:
The end results should look similar to the following.
Now you're ready to build your DKE project.
Build the project
Use the following instructions to build the DKE project locally:
In Visual Studio Code, in the DKE service repository, select View > Command Palette and then type build at the prompt.
From the list, choose Tasks: Run build task.
If there are no build tasks found, select Configure Build Task and create one for .NET core as follows.
Choose Create tasks.json from template.
From the list of template types, select .NET Core.
In the build section, locate the path to the customerkeystore.csproj file. If it's not there, add the following line:
Run the build again.
Verify that there are no red errors in the output window.
If there are red errors, check the console output. Ensure that you completed all the previous steps correctly and the correct build versions are present.
Select Run > Start Debugging to debug the process. If you're prompted to select an environment, select .NET core.
The .NET core debugger typically launches to
https://localhost:5001. To view your test key, go to
https://localhost:5001 and append a forward slash (/) and the name of your key. For example:
The key should display in JSON format.
Your setup is now complete. Before you publish the keystore, in appsettings.json, for the JwtAudience setting, ensure the value for hostname exactly matches your App Service host name. You may have changed it to localhost to troubleshoot the build.
Deploy the DKE service and publish the key store
For production deployments, deploy the service either in a third-party cloud or publish to an on-premises system.
You may prefer other methods to deploy your keys. Select the method that works best for your organization.
For pilot deployments, you can deploy in Azure and get started right away.
To create an Azure Web App instance to host your DKE deployment
To publish the key store, you'll create an Azure App Service instance to host your DKE deployment. Next, you'll publish your generated keys to Azure.
In your browser, sign in to the Microsoft Azure portal, and go to App Services > Add.
Select your subscription and resource group and define your instance details.
Enter the hostname of the computer where you want to install the DKE service. Make sure it's the same name as the one defined for the JwtAudience setting in the appsettings.json file. The value you provide for the name is also the WebAppInstanceName.
For Publish, select code, and for Runtime stack, select .NET Core 3.1.
At the bottom of the page, select Review + create, and then select Add.
Do one of the following to publish your generated keys:
Publish via ZipDeployUI
For example: https://dkeservice.scm.azurewebsites.net/ZipDeployUI
In the codebase for the key store, go to the customer-key-store\src\customer-key-store folder, and verify that this folder contains the customerkeystore.csproj file.
Run: dotnet publish
The output window displays the directory where the publish was deployed.
Send all files in the publish directory to a .zip file. When creating the .zip file, make sure that all files in the directory are at the root level of the .zip file.
Drag and drop the .zip file you create to the ZipDeployUI site you opened above. For example: https://dkeservice.scm.azurewebsites.net/ZipDeployUI
DKE is deployed and you can browse to the test keys you've created. Continue to Validate your deployment below.
Publish via FTP
Connect to the App Service you created above.
In your browser, go to: Azure portal > App Service > Deployment Center > Manual Deployment > FTP > Dashboard.
Copy the connection strings displayed to a local file. You'll use these strings to connect to the Web App Service and upload files via FTP.
In the codebase for the key storage, go to the customer-key-store\src\customer-key-store directory.
Verify that this directory contains the customerkeystore.csproj file.
Run: dotnet publish
The output contains the directory where the publish was deployed.
Send all files in the publish directory to a zip file. When creating the .zip file, make sure that all files in the directory are at the root level of the .zip file.
From your FTP client, use the connection information you copied to connect to your App Service. Upload the .zip file you created in the previous step to the root directory of your Web App.
DKE is deployed and you can browse to the test keys you'd created. Next, Validate your deployment.
Validate your deployment
After deploying DKE using one of the methods described above, validate the deployment and the key store settings.
Ensure that no errors appear in the output. When you're ready, register your key store.
Register your key store
The following steps enable you to register your DKE service. Registering your DKE service is the last step in deploying DKE before you can start creating labels.
To register the DKE service:
In your browser, open the Microsoft Azure portal, and go to All Services > Identity > App Registrations.
Select New registration, and enter a meaningful name.
Select an account type from the options displayed.
If you're using Microsoft Azure with a non-custom domain, such as onmicrosoft.com, select Accounts in this organizational directory only (Microsoft only - Single tenant).
At the bottom of the page, select Register to create the new App Registration.
In your new App Registration, in the left pane, under Manage, select Authentication.
Select Add a platform.
On the Configure platforms popup, select Web.
Under Redirect URIs, enter the URI of your double key encryption service. Enter the App Service URL, including both the hostname and domain.
For example: https://mydkeservicetest.com
- The URL you enter must match the hostname where your DKE service is deployed.
- If you're testing locally with Visual Studio, use https://localhost:5001.
- In all cases, the scheme must be https.
Ensure the hostname exactly matches your App Service hostname. You may have changed it to
localhostto troubleshoot the build. In appsettings.json, this value is the hostname you set for
Under Implicit grant, select the ID tokens checkbox.
Select Save to save your changes.
On the left pane, select Expose an API, then next to Application ID URI, select Set.
Still on the Expose an API page, in the Scopes defined by this API area, select Add a scope. In the new scope:
Define the scope name as user_impersonation.
Select the administrators and users who can consent.
Define any remaining values required.
Select Add scope.
Select Save at the top to save your changes.
Still on the Expose an API page, in the Authorized client applications area, select Add a client application.
In the new client application:
Define the Client ID as d3590ed6-52b3-4102-aeff-aad2292ab01c. This value is the Microsoft Office client ID, and enables Office to obtain an access token for your key store.
Under Authorized scopes, select the user_impersonation scope.
Select Add application.
Select Save at the top to save your changes.
Your DKE service is now registered. Continue by creating labels using DKE.
Create sensitivity labels using DKE
In the Microsoft 365 compliance center, create a new sensitivity label and apply encryption as you would otherwise. Select Use Double Key Encryption and enter the endpoint URL for your key.
Any DKE labels you add will start appearing for users in the latest versions of Microsoft 365 Apps for enterprise.
It may take up to 24 hours for the clients to refresh with the new labels.
Enable DKE in your client
If you're an Office Insider, DKE is enabled for you. Otherwise, enable DKE for your client by adding the following registry keys:
[HKEY_LOCAL_MACHINE\SOFTWARE\WOW6432Node\Microsoft\MSIPC\flighting] "DoubleKeyProtection"=dword:00000001 [HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\MSIPC\flighting] "DoubleKeyProtection"=dword:00000001
Migrate protected files from HYOK labels to DKE labels
If you want, once you're finished setting up DKE, you can migrate content that you've protected using HYOK labels to DKE labels. To migrate, you'll use the AIP scanner. To get started using the scanner, see What is the Azure Information Protection unified labeling scanner?.
If you don't migrate content, your HYOK protected content will remain unaffected.