Azure Active Directory authentication

To use Azure Active Directory (AAD) authentication with Octopus Server, you will need to do the following:

1. Configure AAD to trust your Octopus Deploy instance by setting it up as an App in AAD.
2. Optionally map AAD Users into Roles so you the users can be automatically connected to Octopus Teams.
3. Configure your Octopus Deploy instance to trust and use AAD as an Identity Provider.

Configure Azure Active Directory (AAD)

First, you need to configure your Azure Active Directory to trust your instance of Octopus Deploy by configuring an App in your AAD.

Configure Octopus Deploy as an App in your AAD

1. Log in to the Azure Portal, click on your account positioned at the top-right of the screen, then select your desired directory:

2. Select the hamburger menu in the Azure Portal and select Azure Active Directory from the Azure menu:

3. Select App registrations then choose New application registration:

4. Choose a Name like Octopus Deploy, select the correct Supported account type for Single or Multi-Tenant, and enter a value for Sign-On URL like https://octopus.example.com/api/users/authenticatedToken/AzureAD. Then click Register.

• The URL must use HTTPS.
• When users input their credentials, the value you specify for Name will appear at the top of the Azure authentication page.
• The value you specify for Sign-On URL should be the URL to your Octopus Server. This address is only linked within your browser, so it only has to be resolvable on your network, not from the public Internet.
• Include /api/users/authenticatedToken/AzureAD at the end of your Octopus URL.

Enable ID Tokens and configure

1. Within your new App registration in AzureAD navigate to Authentication.
2. Ensure the ID Tokens box is enabled:

Enable Logout URL if using Single Sign-On (optional)

1. Within your new App registration in AzureAD navigate to Authentication.
2. Input logout URL and enter https://octopus.example.com/app#/users/sign-out substituting your URL.

Mapping AAD users into Octopus teams (optional)

If you want to manage user/team membership via AAD, you need to configure Roles for your App. To add a Role(s), you need to edit the App's manifest.

1. Under the App Registration, select Manifest, and then you can start editing your manifest file as required.

The example below illustrates two roles, one for administrators and one for application testers. You need to create each required group in the Manifest file.

{
  "appId": "myAppGuid",
  "appRoles": [
   {
      "id": "NEWGUID1",
      "allowedMemberTypes": ["User"],
      "description": "OctopusAdministrators",
      "displayName": "OctopusAdmins",
      "isEnabled": true,
      "value": "octopusAdmins"
   },
   {
      "id": "NEWGUID2",
      "allowedMemberTypes": ["User"],
      "description": "OctopusTesters",
      "displayName": "OctopusTesters",
      "isEnabled": true,
      "value": "octopusTesters"
   }
  ]
}

After you have completed editing the manifest, select the Save option.

Configure users and groups in Azure AD (optional)

After the App Role(s) have been defined, users/groups from Azure AD may be mapped into these Roles.

1. Under the App Registration, select your App registrations name under Managed application in local directory.

2. Choose Users and groups and select Add user to create a new role assignment.

3. Select the users you would like to assign roles to. Next, under Select Role, specify one of the AppRoles that you added to the App registration manifest.

4. To save your changes, select the Assign button.

Configure Octopus Server

Get the client ID and Issuer

There are two values you need from the Azure AD configuration to complete the Octopus configuration: the Client ID and Issuer.

Using the Azure portal

In the Azure portal, you can see the Application (client) ID and Directory (tenant) ID on your App's Overview page.

Setting the client ID and Issuer in Octopus Deploy

When you have those values, run the following from a command prompt in the folder where you installed Octopus Server:

Octopus.Server.exe configure --azureADIsEnabled=true --azureADIssuer=Issuer --azureADClientId=ClientID

#Eg:
# Octopus.Server.exe configure --azureADIsEnabled=true --azureADIssuer=https://login.microsoftonline.com/12341234-xxxx-xxxx-xxxx-xxxxxxxxxxxx --azureADClientId=43214321-xxxx-xxxx-xxxx-xxxxxxxxxxxx

Alternatively, these settings can be defined through the user interface by selecting Configuration ➜ Settings ➜ Azure AD and populating the fields Issuer, ClientId, and IsEnabled.

Assign app registration roles to Octopus teams (optional)

If you followed the optional steps to modify the App registration's manifest to include new roles, you can assign them to Teams in the Octopus Portal.

1. Open the Octopus Portal and select Configuration ➜ Teams.

2. Either create a new Team or choose an existing one.

3. Under the Members section, select the option Add External Group/Role.

4. Enter the details from your App registration's manifest. In this example, we need to supply octopusTesters as the Group/Role ID and OctopusTesters as the Display Name.

5. Save your changes by clicking the Save button.

Octopus user accounts are still required

Even if you are using an external identity provider, Octopus still requires a user account, so that you can assign those people to Octopus teams and subsequently grant permissions to Octopus resources. Octopus will automatically create a user account based on the profile information returned in the security token, which includes an Identifier, Name, and Email Address.

How Octopus matches external identities to user accounts

When the security token is returned from the external identity provider, Octopus looks for a user account with a matching Identifier. If there is no match, Octopus looks for a user account with a matching Email Address. If a user account is found, the external identifier will be added to the user account for next time. If a user account is not found, Octopus will create one using the profile information in the security token.

Getting permissions

If you are installing a clean instance of Octopus Deploy you will need to seed it with at least one admin user. This user will have access to create and configure other users as required. To add a user, execute the following command

Octopus.Server.exe admin --username USERNAME --email EMAIL

The most important part of this command is the email, as usernames are not necessarily included in the claims from the external providers. When the user logs in the matching logic must be able to align their user record based on the email from the external provider or they will not be granted permissions.

Next steps

Now that you're using an external identity provider, it is easy to increase your security. You could consider configuring Multi-Factor Authentication, after all, Octopus Deploy has access to your production environments!

You should also consider disabling any authentication providers you aren't using, like username and password authentication.

Troubleshooting

If you are having difficulty configuring Octopus to authenticate with Azure Active Directory, check your server logs for warnings.

Triple check your configuration

Unfortunately, the security-related configuration is sensitive to everything. Make sure:

• You don't have any typos or copy-paste errors.
• Remember, things are case-sensitive.
• Remember to remove or add slash characters.

Check the OpenID Connect metadata is working

You can see the OpenID Connect metadata by going to the Issuer address in your browser and adding /.well-known/openid-configuration to the end. In our example, this would be something like https://login.microsoftonline.com/b91ebf6a-84be-4c6f-97f3-32a1d0a11c8a/.well-known/openid-configuration.

Inspect the contents of the security token

Sometimes the contents of the security token sent back by Azure AD aren't exactly what Octopus expects; certain claims might be missing or named differently. This will usually result in the Azure AD user incorrectly mapping to a different Octopus user than expected. The best way to diagnose this is to inspect the JSON Web Token (JWT), which is sent from Azure AD to Octopus via your browser. To inspect the contents of your security token:

1. Open the Developer Tools of your browser and enable Network logging, making sure the network logging is preserved across requests.
2. In Chrome Dev Tools, this is called "Preserve Log".

3. Attempt to sign into Octopus using Azure AD and find the HTTP POST coming back to your Octopus instance from Azure AD on a route like /api/users/authenticatedToken/azureAD. You should see an id_token field in the HTTP POST body.
4. Grab the contents of the id_token field and paste that into https://jwt.io/, which will decode the token for you.

5. Don't worry if jwt.io complains about the token signature; it doesn't support RS256, which is used by Azure AD.
6. Octopus uses most of the data to validate the token, but primarily uses the sub, email, and name claims. If these claims are not present, you will likely see unexpected behavior.

Contact Octopus Support

If you aren't able to resolve the authentication problems yourself using these troubleshooting tips, please reach out to our support team with:

1. The contents of your OpenID Connect Metadata or the link to download it (see above) can be different for each Azure AD App.
2. A copy of the decoded payload for some security tokens (see above) may work as expected, and others will not.
3. A screenshot of the Octopus User Accounts, including their username, email address, and name.

Need support? We're here to help.