I have a project that is a website authenticated with a smart card (DoD CAC). I need to make multiple test certificates that the site can use for client authenticating the session. It seems possible to have a non-smartcard-based certificate that a user can choose for client authentication.

I feel comfortable saying this because when I hit my dev site on my MacBook, it shows me 2 Apple certificates. Those won't work because our authentication process requires a short sequence of numbers at the end of the common name.


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I have tried SO many different things, I simply cannot create a certificate that presents along with my DoD CAC certs when hitting the site. In the certificate manager the Mac certificate, the DoC CACs and my test certs are showing "Client Authentication" in the Intended Purposes field. I also have the self-signed cert that I used as the CA for my test cert in trusted roots.

The DoD certs have "Smart Card Logon" and "Client Authentication" in the Intended Purposes field. I can only specify 1 eku when using makecert.exe, so I can make the certificate with a "Client Authentication" or "Smart Card Logon" value, but not both. It would seem logical that I only need the certificate to be set with "Client Authentication".

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*Important note about Apostille and Certification of Authentication Services: Apostille and Certification of Authentication documents may be dropped off for processing. Customers may provide prepaid envelopes for priority returns. Individuals who have a documented emergency circumstance or travel plans within two weeks may schedule an appointment to have their documents completed at our Albany or New York City customer service office. For further information, please visit  -or-certificate-authentication

There is another option if nFactor is used, through nFactor, you can offload the authentication to the AAA vServer. In nFactor, you can just force users to have cert authentication based on policy expressions. No need of setting cert auth as mandatory on the CAG.

This article describes how to enable user certificate authentication in Active Directory Federation Services (AD FS). It also provides troubleshooting information for common problems with this type of authentication.

Enable user certificate authentication as an intranet or extranet authentication method in AD FS, by using either the AD FS Management console or the PowerShell cmdlet Set-AdfsGlobalAuthenticationPolicy.

If you want to use claims based on certificate fields and extensions in addition to the EKU claim type, , configure more claim passthrough rules on the Active Directory claims provider trust. See the complete list of available certificate claims later in this article.

If you need to restrict access based on the type of certificate, you can use the additional properties on the certificate in AD FS issuance authorization rules for the application. Common scenarios are to allow only certificates provisioned by a mobile device management (MDM) provider or to allow only smart card certificates.

Customers who use device code flow for authentication and perform device authentication by using an identity provider other than Microsoft Entra ID (for example, AD FS) can't enforce device-based access for Microsoft Entra resources. For example, they can't allow only managed devices by using a third-party MDM service.

Consider modifying sign-in pages to suit the needs of your users when they're doing certificate authentication. A common case is to change Sign in with your X509 certificate to something more user friendly.

When a machine has multiple user certificates (such as Wi-Fi certificates) that satisfy the purposes of client authentication, the Chrome browser on Windows desktops will prompt users to select the right certificate. This prompt might be confusing to users. To optimize this experience, you can set a policy for Chrome to automatically select the right certificate.

You can set this policy manually by making a registry change, or you can configure it automatically via GPO (to set the registry keys). This requires your user client certificates for authentication against AD FS to have distinct issuers from other use cases.

AD FS uses the underlying Windows operating system to prove possession of the user certificate and ensure that it matches a trusted issuer by validating the certificate trust chain. To match the trusted issuer, you need to ensure that all root and intermediate authorities are configured as trusted issuers in the local store for computer certificate authorities.

AD FS performs user certificate authentication by default on port 49443 with the same hostname as AD FS (example: adfs.contoso.com). You can also configure AD FS to use port 443 (the default HTTPS port) by using the alternate SSL binding. However, the URL used in this configuration is certauth. (example: certauth.contoso.com). For more information, see AD FS support for alternate hostname binding for certificate authentication.

In AD FS on Windows Server 2016, two modes are now supported. The first mode uses the host adfs.contoso.com with ports 443 and 49443. The second mode uses hosts adfs.contoso.com and certauth.adfs.contoso.com with port 443. You need an SSL certificate to support certauth.\ as an alternate subject name. You can do this at the time of farm creation or later via PowerShell.

The most common case of network connectivity problems is that a firewall has been incorrectly configured and blocks traffic for user certificate authentication. Usually, you see a blank screen or a 500 server error when this problem occurs. To fix it:

Certificate revocation lists (CRLs) are endpoints that are encoded into the user certificate to perform runtime revocation checks. For example, if a device that contains a certificate is stolen, an administrator can add the certificate to the list of revoked certificates. Any endpoint that accepted this certificate earlier will now fail the authentication.

Every AD FS and WAP server needs to reach the CRL endpoint to validate if the certificate that was presented to it is still valid and hasn't been revoked. CRL validation can occur over HTTPS, HTTP, LDAP, or OCSP. If AD FS and WAP servers can't reach the endpoint, the authentication will fail. Use the following steps to troubleshoot it:

You might notice that some devices are working correctly but other devices are not. In most cases, it means that the user certificate wasn't provisioned correctly on some client devices. Follow these steps:

If the problem is specific to an Android device, the most common cause is that the certificate chain is not fully trusted on the device. Refer to your MDM vendor to ensure that the certificate has been provisioned correctly and the entire chain is fully trusted on the Android device.

Many Office 365 applications send prompt=login to Microsoft Entra ID. Microsoft Entra ID, by default, converts it to a fresh password login to AD FS. As a result, even if you configured certificate authentication in AD FS, your users see only a password login. To fix this problem:

PIV credentials have certificates and key pairs, pin numbers, biometrics like fingerprints and pictures, and other unique identifiers. When these items are put together in a PIV credential, the credential provides the capability to implement multifactor authentication for networks, applications, and buildings.

Agency security is enhanced when PIV credentials are used for authentication to agency systems and facilities. PIV credentials allow for a high level of assurance in the individuals who that access your resources, because the credentials are only issued by trusted providers to individuals who that have been verified in person. PIV credentials are highly resistant to identity fraud, tampering, counterfeiting, and exploitation.

Your PIV credential from one agency will have the same basic required format, information, and technology as a PIV credential from your partner agencies. This allows us to trust each other, share applications, and architect and implement systems using common patterns for authentication.

Any system at your organization that requires heightened security for determining who should gain access can and should use PIV for authentication. While PIV credentials can be used for authentication on almost any system, they are especially useful for systems that protect sensitive information.

The Card Authentication, PIV Authentication, Digital Signature, and Encryption all leverage four separate certificates and key pairs issued from certificate authorities that are audited and certified by the Federal Public Key Infrastructure (FPKI).

Card readers are available in many shapes and sizes to fit both the PIV credential and to plug into your computer. There is a card reader that will work for any shape and size computer you use, including card readers for USB and microUSB ports. Examples of readers include fold-up readers, desk readers, keyboard readers, tablet readers, and laptop readers. 006ab0faaa

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