CertKit Agent Support for Always On VPN SSTP and DirectAccess IP-HTTPS TLS Certificates

With public TLS certificate lifetimes set to drop to 200 days soon (next week!), Always On VPN and DirectAccess administrators face an increased risk of service disruption if certificates aren’t renewed on time. These shorter certificate lifetimes require more frequent renewals, substantially increasing management overhead. Although 200 days equate to roughly a twice-a-year renewal, lifetimes will decrease further to 100 days next year and eventually to just 47 days in 2029. SSTP and IP-HTTPS are TLS-based tunneling protocols used by Always On VPN and DirectAccess, respectively, tying their certificate health directly to remote access availability. Now is the time to automate the enrollment and renewal of Always On VPN SSTP and DirectAccess IP-HTTPS/TLS certificates to ensure reliable operation in the future.

Always On VPN

Previously, I wrote about using CertKit.io to automate the enrollment and renewal of public TLS certificates for Always On VPN. CertKit is an online service that administrators can use to delegate the task of enrolling for short-lived certificates from Let’s Encrypt. In that post, I shared some sample code to retrieve the certificate from CertKit and assign it to the SSTP listener for the Routing and Remote Access Service (RRAS). However, CertKit added new features to its solution, eliminating the need for additional code.

CertKit Agents

Recently, CertKit introduced CertKit Agents. These lightweight software agents are installed on Windows Servers (other operating systems are supported as well) to automate the process of downloading CertKit certificates and installing them in the local computer certificate store. Importantly, they now specifically support both the Always On VPN (SSTP) and DirectAccess (IP-HTTPS) workloads natively.

Always On VPN

The CertKit agent automatically detects the Routing and Remote Access (RRAS) workload and updates the certificate binding for the SSTP listener accordingly. Since this process requires a service restart, which terminates all current VPN connections, CertKit allows you to select an outage window for certificate updates.

Here, administrators can define the day(s) and time window during which the agent is authorized to restart the RemoteAccess service when updating the TLS certificate for SSTP. The day and time are based on the server’s configured time zone settings.

DirectAccess

Beginning with CertKit agent v1.6.2, the agent automatically detects whether DirectAccess is configured, enabling IP-HTTPS TLS certificates to be automatically enrolled and renewed. However, additional configuration is required. The following changes must be made to support CertKit for DirectAccess.

  • Service Account – Administrators must configure a service account in Active Directory for the CertKit agent. A Group Managed Service Account (gMSA) is preferred, but a standard domain service account is also supported.
  • GPO Delegation – CertKit service account must be delegated the ‘Edit settings, delete, and modify security’ permission on the DirectAccess server and client settings GPOs.
  • Log On as a Service – When using a domain service account, administrators must grant the CertKit service the ‘Log on as a service’ right on the DirectAccess server. However, when using gMSA, the ‘Log on as a service’ right is not required.
  • Local Administrator – Administrators must also add the CertKit agent service account to the Local Administrators group on the server.

Configuration Script

I have published a PowerShell script to simplify configuring the CertKit agent on DirectAccess servers. The script automatically performs all required tasks for the CertKit agent to work with DirectAccess. You will find the Enable-DACertKit.ps1 PowerShell script on GitHub. Alternatively, you can install the script directly from the PowerShell Gallery.

Install-Script -Name Enable-DACertKit -Scope CurrentUser

After installing the CertKit agent, run the PowerShell script to complete the configuration. Next, authorize the agent in the CertKit management portal and assign a certificate. Once complete, CertKit can fully manage the IP-HTTPS TLS certificate for DirectAccess.

Note: Like Always On VPN, changes to the DirectAccess IP-HTTPS certificate require a service restart, which is disruptive. Be sure to define a maintenance window (as shown previously) to ensure the change is made during non-peak times.

Summary

As TLS certificate lifecycles continue to shrink, automating certificate enrollment and renewal has become essential for both Always On VPN and DirectAccess environments. CertKit agents streamline this process by automatically retrieving, installing, and binding certificates for SSTP and IP-HTTPS, all while supporting scheduled outage windows to minimize disruption. With these new capabilities, administrators can significantly reduce operational overhead and ensure consistent, reliable remote access services without manual intervention. Visit CertKit.io to get started today.

More Information

If you would like to learn more about CertKit or see a demonstration with Always On VPN or DirectAccess, fill out the form below, and I’ll provide you with more details.

Additional Information

Always On VPN SSTP Certificate Automation with CertKit

CertKit Agents

Enable-DACertKit.ps1 on GitHub

Enable Group Managed Service Accounts

The Myth of the Publish Certificate in Active Directory Setting

Certificate templates in Microsoft Active Directory Certificate Services (AD CS) provide powerful, preconfigured settings that enable administrators to issue certificates tailored for specific purposes. For example, a certificate template could allow a user to authenticate to a Wi-Fi network or VPN gateway. Another template might control policies for enrolling for web server certificates in the enterprise. Templates define settings such as cryptographic parameters (key algorithm and length), validity period, application policies, enrollment requirements, and more. While there are myriad settings to choose from, one in particular is often enabled unnecessarily. And while it works without issue, there can be some hidden downsides to enabling this setting.

Publish Certificate in Active Directory

When creating a certificate template, there’s an option on the General tab called Publish certificate in Active Directory. From experience, this is one of the most misunderstood settings for certificate templates.

Intuitively, it would make sense to check this box on all published certificate templates. After all, I want the users or devices targeted by this certificate template to find them in Active Directory (AD) so they can enroll. Many administrators believe that enabling this setting is required to ‘see’ the published certificate template on the endpoint, as shown here.

However, enabling the Publish certificate in Active Directory option is not required for enrollment. To ‘see’ certificates available for enrollment, the user or device must only have the Enroll permission on the template.

What Is It For?

So, what does the Publish certificate in Active Directory setting do? When this option is enabled, the issuing CA adds the certificate to the requesting principal’s Active Directory account. There are two common scenarios where this is required.

S/MIME

Adding a user’s certificate to their AD account makes the public key centrally discoverable, allowing Outlook and other S/MIME-enabled clients to automatically find recipients’ certificates for secure email encryption and signature validation. Without the certificate published in AD, users must manually exchange certificates, breaking seamless S/MIME encryption in most enterprise environments.

Encrypting File System (EFS)

Publishing a user’s EFS certificate to their Active Directory account allows Windows to locate the correct public key automatically when encrypting files. It ensures recovery agents and key archival processes function properly. Without the certificate in AD, EFS can fail to encrypt data consistently across machines or prevent access to encrypted files when users roam or recover profiles.

Drawbacks

There are very few scenarios outside of S/MIME and EFS that require the Publish certificate in Active Directory option to be enabled. However, enabling it doesn’t necessarily break anything, and this setting is often enabled by default (or carried over from the source template when duplicating), so administrators may miss this option. Issuing certificates in this way introduces some potential problems.

AD Database Bloat

Adding a certificate to each principal’s AD object increases the size of each object, thereby increasing the total size of the AD database. For organizations with large directories with hundreds of thousands or even millions of accounts, adding unnecessary data to each account can be very expensive in terms of database size, replication traffic, backup storage, and overall domain performance. Making matters worse, certificates published to AD live perpetually. They are not removed automatically when certificates are revoked or expire.

Service Accounts

Service accounts used for certificate enrollment, such as the Microsoft Intune Certificate connector, can be especially challenging. Here, if the Publish certificate in Active Directory setting is enabled on the Intune certificate template, the CA will add a certificate to the service account for every certificate it issues. While you can have many certificates associated with a single account, there is an upper limit, approximately 1250, based on my testing. After that, certificates will continue to be issued, but adding them to AD will fail.

Remediation

The following recommendations can help administrators correct this misconfiguration and limit its impact in their environment.

Disable Unnecessary Certificate Publishing

Administrators should clear the Publish certificate in Active Directory setting on all certificate templates that do not explicitly require it, such as those used for S/MIME or Encrypting File System (EFS). This prevents new certificates from being written to user or computer objects and does not require certificates to be reissued.

Remove Published Certificates

Administrators can remove unnecessary certificates from user, computer, and service account objects in AD to reduce object and overall AD database sizes. Perform the following steps to remove unneeded certificates.

  1. Open the Active Directory Users and Computers management console (dsa.msc) and double-click the target principal.
  2. Select the Published Certificates tab.
  3. Select a certificate (or all certificates) and click Remove.

Important Note: Use extreme caution when deleting certificates! Do not delete any certificates unless you are certain they are not required.

Managed Service Accounts

Managed Service Accounts in AD do not have a Published Certificates tab. Administrators can use the Attribute Editor to remove individual certificates from the userCertificate attribute on the account.

Managed Service Account Attribute Editor

Managed Service Account userCertificate Entries

Unfortunately, there is no option to view the certificate in the UI for Managed Service Accounts. To view detailed certificate information, see the PowerShell section below.

Existing Certificates Are Not Removed Automatically

Disabling the Publish certificate in Active Directory setting only stops future certificates from being published in AD. Certificates already written to Active Directory are never removed automatically, even after they expire or are revoked. In environments where this setting has been enabled for an extended period, large numbers of stale certificates often accumulate and continue to increase the AD database size.

Intune Certificate Connector Considerations

This issue is especially problematic for high-volume enrollment scenarios that use service accounts, such as the Microsoft Intune Certificate Connector. When publishing is enabled for Intune certificate templates, certificates issued on behalf of users are added to the service account, quickly leading to excessive certificate accumulation and potential attribute limits.

ADPrincipalCertificate PowerShell Module

Manually performing this cleanup at scale is impractical. To assist administrators with cleaning up unnecessarily published certificates, I’ve created the ADPrincipalCertificate PowerShell module. This module includes functions to enumerate AD accounts that include certificates, show and optionally export certificates for AD accounts, and remove published certificates. The module also includes a function to enumerate published certificate templates that include the Publish certificate in Active Directory option enabled. You can install the ADPrincipalCertificate PowerShell module from the PowerShell gallery by running the following command.

Install-Module -Name ADPrincipalCertificate -Scope CurrentUser

See the ADPrincipalCertificate GitHub repository for detailed usage information.

Summary

While the Publish certificate in Active Directory option is helpful for S/MIME and EFS deployments, it is unnecessary for most other scenarios and is often enabled when it isn’t needed. This results in the unnecessary addition of certificates to AD accounts, causing individual objects and the entire AD database to grow without benefit. Sadly, many vendor guides indicate that this setting is required when it often isn’t, so many environments suffer from this misconfiguration. Administrators should review the certificate template configuration and disable this setting when it isn’t needed. Additionally, use the ADPrincipalCertificate PowerShell module to perform cleanup, if required.

Additional Information

ADPrincipalCertificate PowerShell Module on GitHub

ADPrincipalCertificate PowerShell Module in the PowerShell Gallery

Always On VPN SSTP Certificate Automation with CertKit

With public TLS certificates moving to significantly shorter certificate lifetimes, eventually just 47 days, Always On VPN administrators supporting Secure Socket Tunneling Protocol (SSTP) connections must prepare to address this eventuality. The first milestone for shortened public TLS certificate lifetimes is a few months, on March 15, 2026, when public TLS certificate lifetimes will be reduced from a maximum of 398 days to 200 days. One year later, on March 15, 2027, they will be reduced to just 100 days. Now is the time to begin planning an automated certificate enrollment solution to reduce administrative overhead and ensure uninterrupted connectivity for remote users.

Previous Approaches: PowerShell and Posh-ACME

In the past, I’ve written about using Let’s Encrypt Certificates for Always On VPN using the Posh-ACME PowerShell module. I’ve also posted some sample code to demonstrate how to integrate with a DNS provider to automate publishing the ACME challenge to public DNS for certificate enrollment verification. However, this assumes your DNS provider supports this option. Some do not. In addition, granting write permissions to public DNS via an API key introduces significant security risks. So, if direct ACME DNS automation isn’t viable in your environment, CertKit is an excellent alternative.

CertKit: Automated Certificate Issuance, Monitoring, and Alerting

To address these limitations, administrators can use the CertKit service. With CertKit, you delegate the Let’s Encrypt certificate enrollment process to them by simply creating a CNAME record in your public DNS. Once complete, CertKit handles the entire process transparently.

Issuance

Today, CertKit supports issuing certificates using Let’s Encrypt. In the future, support for additional certificate providers such as Google Trust and ZeroSSL will be added. CertKit supports Let’s Encrypt certificates using RSA (2048-bit) and Elliptic Curve (recommended). Certificates can be issued for an individual resource, a group of resources (multi-SAN), and a domain wildcard (e.g., *.example.net).

Monitoring

In addition to certificate issuance and management, CertKit offers domain TLS certificate monitoring to track your public assets. You can monitor your CertKit-managed certificates easily, but you can also add other services using TLS and track them on the same console. In this example, I’m using CertKit to manage certificates for two VPN servers (indicated by solid green dots) and to monitor my public websites, for which certificate management is handled by their respective hosting providers.

Alerts and Notifications

CertKit will automatically send emails to let you know when a certificate is expiring and if a CertKit-managed certificate has been renewed.

Pending certificate expiration.

Successful certificate renewal.

Certificate Retrieval

Once CertKit completes the enrollment process on your behalf, it stores all certificate files (.PFX, .PEM, and .KEY) in a secure S3-compatible storage bucket. While an administrator could easily retrieve and install them manually, automation will help reduce administrative overhead, especially as public TLS certificate lifetimes are further reduced. You can download certificate files programmatically in several ways.

PowerShell

The first way to download the certificate files from CertKit is to use the AWSPowerShell module. However, the AWSPowerShell is relatively heavy and is overkill for this specific use case. A better alternative is to use the MinIO client.

MinIO

The MinIO client (mc.exe) is an open-source command-line tool developed by MinIO. It provides access to any S3-compatible storage, which CertKit uses in its environment. MinIO is a single, portable executable installer that’s easy to use and well-documented.

Sample Code

I’ve published some sample code to demonstrate how to use the MinIO client to retrieve certificates from CertKit and install them on a Windows Server Routing and Remote Access (RRAS) server. You can find the sample code on GitHub here.

https://github.com/richardhicks/aovpn/blob/master/Install-SstpLetsEncryptCertificate-Certkit.ps1

Note: This sample code demonstrates how to download a .PFX file from CertKit and install it on the RRAS server. It is designed to run as a scheduled task in Windows during non-peak times. The code includes robust checks for service viability and will reboot the server if they fail. As such, this sample code could cause service disruptions, so use it with caution.

Cost

Today, CertKit is in beta and is free for everyone to use. In the future, there will be both free and paid tiers. You can learn more about their pricing models and sign up for the service at CertKit.io.

Learn More

If you’d like to learn more about CertKit and how you can leverage it for Always On VPN and other workloads in your environment, or you’d like to see a demonstration of CertKit, fill out the form below, and I’ll provide you with more information.

Additional Information

CertKit

Install-SstpLetsEncryptCertificate-Certkit.ps1 on GitHub

Always On VPN SSTP and 47-Day TLS Certificates

Always On VPN SSTP with Let’s Encrypt Certificates