Gregg O’Brien is a Microsoft Premier Field Engineer from Canada. In this post he talks about the ‘certificate explosion’ phenomenon and suggests a way to mitigate it.

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• On an AD FS server, client certificate authentication enables a user to authenticate using, for example, a smart card. If your AD FS server (version 3.0 or 4.0) is configured to support client certificate authentication using an alternate port, you can use this implementation to enable an Access Policy Manager ® (APM ®) AD FS proxy to provide the same support.
• Nov 15, 2019  Developers can build applications that leverage the common identity model, integrating applications into Active Directory on-premises or Azure for cloud-based applications; Azure AD Connect makes this integration easy and simplifies the management of your on.

Introduction

We live in some very exciting times – we have so many devices to choose from: desktops, laptops, tablets, hybrids/convertibles, ultrabooks, netbooks and smartphones. Each of these devices offer their own unique benefits and features, so much so that it’s not uncommon to find people carrying 2 or 3 devices now!

As with all super cool technology though, IT pros will always find some challenge waiting at the bottom of that pile of coolness. In the case of multiple devices in an enterprise, a common problem is enrollment of certificates. Not so much a problem of acquiring certificates, but the problem of users acquiring too many certificates.

Scenario

A Microsoft Active Directory Certificate Services infrastructure on Windows Server 2008/2012 is implemented with auto-enrollment capabilities. Users with accounts in Active Directory login to the domain and the auto-enrollment policy enrolls the user for a certificate tied to their account. The certificate is downloaded from the certificate authority and is stored in the user’s certificate store on the local computer. So far so good….

Now for the ‘wrench in the gears’: the same user logs into another computer with the same user account and because the certificate store tied to that user account is empty on the second computer, the user receives a new certificate with a different private key. This behavior repeats on every computer the user logs on to. At first this might not seem like such a big deal. But this actually presents a few potential issues:

1. Operations carried out on the local PC such as drive encryption will use certificate stored in the local computer store. When the user logs into a different machine and a new certificate is requested, a different private key will be used for local operations. Meaning that the user will have multiple private keys that will not be able to perform operations on data from another computer, even if it is a device that they own!
2. The certificate is stored in the user’s local profile. If that profile is lost, so is the certificate with the private key! If that key isn’t backed up, the data protected with that private key is lost.
3. The certificate services database gets larger unnecessarily due to each user in the organization having multiple certificates.

The Solution

So what can we do about this? Well, the good news is, unlike most complex problems in life this one can be fixed by checking a few check boxes:

• Launch the Certificate Templates Snap-in
• Locate the template that users are being enrolled for certificates from. On my server, I called it “User Certificates”:
• Right click on the template and click “Properties”:

• On the general tab locate the check box for “Publish certificate in Active Directory” and ensure it is checked.
• Check the box below called “Do not automatically reenroll if a duplicate certificate exists in Active Directory”

• Click “Apply” and then click “OK”
• Now launch the “Certificate Authority” console and click on Certificate Templates. We will reissue the User Certificates template to update for the changes.
• Click on the “Certificate Templates” node and find the User Certificates template being used from the pane on the right.
• Right click on the template and click “Delete” and answer “Yes”

• Now right click on the “Certificate Templates” node and click on “New” and then “New Template to Issue”

• Locate the template being used for User Certificates and then click “OK”

Conclusion

Now when users enroll for a certificate, the client will first check it see if there is a certificate in Active Directory. If there is, rather than issuing a new certificate it will reuse the certificate that has already been issued. Another technical challenge vanquished!

Posted by Arvind Shyamsundar, MSPFE Editor.

This topic describes tasks and procedures that you can perform to ensure that your AD FS token signing and token decryption certificates are up to date.

Token signing certificates are standard X509 certificates that are used to securely sign all tokens that the federation server issues. Token decryption certificates are standard X509 certificates that are used to decrypt any incoming tokens. They are also published in federation metadata.

For additional information see Certificate Requirements

Determine whether AD FS renews the certificates automatically

By default, AD FS is configured to generate token signing and token decryption certificates automatically, both at the initial configuration time and when the certificates are approaching their expiration date.

You can run the following Windows PowerShell command: Get-AdfsProperties.

The AutoCertificateRollover property describes whether AD FS is configured to renew token signing and token decrypting certificates automatically.

If AutoCertificateRollover is set to TRUE, the AD FS certificates will be renewed and configured in AD FS automatically. Once the new certificate is configured, in order to avoid an outage, you must ensure that each federation partner (represented in your AD FS farm by either relying party trusts or claims provider trusts) is updated with this new certificate.

If AD FS is not configured to renew token signing and token decrypting certificates automatically (if AutoCertificateRollover is set to False), AD FS will not automatically generate or start using new token signing or token decrypting certificates. You will have to perform these tasks manually.

If AD FS is configured to renew token signing and token decrypting certificates automatically (AutoCertificateRollover is set to TRUE), you can determine when they will be renewed:

CertificateGenerationThreshold describes how many days in advance of the certificate's Not After date a new certificate will be generated.

CertificatePromotionThreshold determines how many days after the new certificate is generated that it will be promoted to be the primary certificate (in other words, AD FS will start using it to sign tokens it issues and decrypt tokens from identity providers).

If AD FS is configured to renew token signing and token decrypting certificates automatically (AutoCertificateRollover is set to TRUE), you can determine when they will be renewed:

• CertificateGenerationThreshold describes how many days in advance of the certificate's Not After date a new certificate will be generated.
• CertificatePromotionThreshold determines how many days after the new certificate is generated that it will be promoted to be the primary certificate (in other words, AD FS will start using it to sign tokens it issues and decrypt tokens from identity providers).

Determine when the current certificates expire

You can use the following procedure to identify the primary token signing and token decrypting certificates and to determine when the current certificates expire.

You can run the following Windows PowerShell command: Get-AdfsCertificate –CertificateType token-signing (or Get-AdfsCertificate –CertificateType token-decrypting). Or you can examine the current certificates in the MMC: Service->Certificates.

The certificate for which the IsPrimary value is set to True is the certificate that AD FS is currently using.

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The date shown for the Not After is the date by which a new primary token signing or decrypting certificate must be configured.

To ensure service continuity, all federation partners (represented in your AD FS farm by either relying party trusts or claims provider trusts) must consume the new token signing and token decryption certificates prior to this expiration. We recommend that you begin planning for this process at least 60 days in advance.

Generating a new self-signed certificate manually prior to the end of the grace period

Canon powershot sx20 is software. You can use the following steps to generate a new self-signed certificate manually prior to the end of the grace period.

1. Ensure that you are logged on to the primary AD FS server.
2. Open Windows PowerShell and run the following command: Add-PSSnapin 'microsoft.adfs.powershell'
3. Optionally, you can check the current signing certificates in AD FS. To do so, run the following command: Get-ADFSCertificate –CertificateType token-signing. Look at the command output to see the Not After dates of any certificates listed.
4. To generate a new certificate, execute the following command to renew and update the certificates on the AD FS server: Update-ADFSCertificate –CertificateType token-signing.
5. Verify the update by running the following command again: Get-ADFSCertificate –CertificateType token-signing
6. Two certificates should be listed now, one of which has a Not After date of approximately one year in the future and for which the IsPrimary value is False.

Important

To avoid a service outage, update the certificate information on Azure AD by running the steps in the How to update Azure AD with a valid token-signing certificate.

If you're not using self-signed certificates…

If you are not using the default automatically generated, self-signed token signing and token decryption certificates, you must renew and configure these certificates manually.

First, you must obtain a new certificate from your certificate authority and import it into the local machine personal certificate store on each federation server. For instructions, see the Import a Certificate article.

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Then you must configure this certificate as the secondary AD FS token signing or decryption certificate. (You configure it as a secondary certificate to allow your federation partners enough time to consume this new certificate before you promote it to the primary certificate).

To configure a new certificate as a secondary certificate

1. Open PowerShell and run the following: Set-ADFSProperties -AutoCertificateRollover $false
2. Once you have imported the certificate. Open the AD FS Management console.
3. Expand Service and then select Certificates.
4. In the Actions pane, click Add Token-Signing Certificate.
   
5. Select the new certificate from the list of displayed certificates, and then click OK.
6. Open PowerShell and run the following: Set-ADFSProperties -AutoCertificateRollover $true

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Warning

Ensure the new certificate has a private key associated with it and that the AD FS service account is granted Read permissions to the private key. Verify this on each federation server. To do so, in the Certificates snap-in, right-click the new certificate, click All Tasks, and then click Manage Private Keys.

Once you've allowed enough time for your federation partners to consume your new certificate (either they pull your federation metadata or you send them the public key of your new certificate), you must promote the secondary certificate to primary certificate.

To promote the new certificate from secondary to primary

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1. Open the AD FS Management console.
2. Expand Service and then select Certificates.
3. Click the secondary token signing certificate.
4. In the Actions pane, click Set As Primary. Click Yes at the confirmation prompt.
   

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Updating federation partners

Partners who can consume Federation Metadata

If you have renewed and configure a new token signing or token decryption certificate, you must make sure that the all your federation partners (resource organization or account organization partners that are represented in your AD FS by relying party trusts and claims provider trusts) have picked up the new certificates.

Partners who can NOT consume Federation Metadata

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If your federation partners cannot consume your federation metadata, you must manually send them the public key of your new token-signing / token-decrypting certificate. Send your new certificate public key (.cer file or .p7b if you wish to include the entire chain) to all of your resource organization or account organization partners (represented in your AD FS by relying party trusts and claims provider trusts). Have the partners implement changes on their side to trust the new certificates.

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Promote to primary (if AutoCertificateRollover is False)

If AutoCertificateRollover is set to False, AD FS will not automatically generate or start using new token signing or token decrypting certificates. You will have to perform these tasks manually.After allowing a sufficient period of time for all of your federation partners to consume the new secondary certificate, promote this secondary certificate to primary (in the MMC snap-in, click the secondary token signing certificate and in the Actions pane, click Set As Primary.)

Updating Azure AD

AD FS provides single sign-on access to Microsoft cloud services such as Office 365 by authenticating users via their existing AD DS credentials. For additional information on using certificates see Renew federation certificates for Office 365 and Azure AD.