The Secure Socket Tunneling Protocol (SSTP) VPN protocol uses Transport Layer Security (TLS) encryption and HTTP transport over TCP port 443. SSTP is easy to configure and firewall-friendly, making it an excellent choice for the Always On VPN user tunnel. Security best practices dictate using a TLS certificate issued by a public Certification Authority (CA). Today, the maximum lifetime of a public TLS certificate is 398 days (approximately 1 year). Always On VPN administrators using SSTP are familiar with the process of renewing their SSTP certificate annually. However, that’s about to change.
47 Days
In April of this year, the CA/Browser Forum, a voluntary consortium of public CAs, browser vendors, and other industry stakeholders that develop and promote security standards and best practices for digital certificates and Public Key Infrastructure (PKI), adopted a measure reducing the current maximum lifetime of public TLS certificates to 47 days. This means Always On VPN administrators using public TLS certificates must eventually update their TLS certificates monthly.
Automation
Of course, no administrator in their right mind would want to renew SSTP certificates every month. Automating this process will be crucial to ensuring reliability and reducing management overhead. I’ll provide more details later in this post.
Why Is This Happening?
The industry has been trending toward shorter certificate lifetimes for a while now. In the old days, you could purchase a certificate valid for 5 years or more. Today, a one-year certificate is all you can get. Let’s Encrypt, a public CA that issues certificates for free, issues only 90-day lifetime certificates.
Advantages
The advantage of using short-lived certificates for public TLS certificates is that they improve security and provide agility for future changes. Public TLS certificates become less secure and trustworthy over time. The longer a certificate is valid, the less trustworthy it becomes and the longer the opportunity for an attacker to leverage a certificate for which the private key has been compromised.
Why 47 Days?
A 47-day maximum certificate lifetime allows administrators to rotate their certificates monthly (a maximum of 31 days plus some margin to resolve issues).
Not So Fast
The good news for Always On VPN administrators using SSTP with public TLS certificates is that they won’t have to worry about this immediately. The reduction in maximum certificate lifetime to 47 days takes place gradually over a few years.
- Today, the maximum public TLS certificate lifetime is 398 days
- On March 15, 2026, the maximum public TLS certificate lifetime will be reduced to 200 days
- On March 15, 2027, the maximum public TLS certificate lifetime will be reduced to 100 days
- On March 15, 2029, the maximum public TLS certificate lifetime will be reduced to 47 days
Let’s Encrypt
Over the years, I’ve deployed Always On VPN with SSTP for several customers using Let’s Encrypt TLS certificates. Let’s Encrypt is a pubic CA that issues certificates with a maximum lifetime of 90 days, so automating this task is essential. Let’s Encrypt supports ACME, a standard protocol for automating the issuance and renewal of TLS certificates, which makes automating TLS certificate installation and renewal a breeze.
Sample Script
I’ve published a sample PowerShell script demonstrating how to automate the enrollment process for Let’s Encrypt TLS certificates. It leverages the Posh-ACME PowerShell module and my AOVPNTools module to enroll and automatically install a TLS certificate for SSTP. This script will also work for DirectAccess. You can find the sample script here.
Note: My sample script demonstrates using the Cloudflare DNS plugin for Posh-ACME. Posh-ACME has plugins for many public DNS providers, which can be found here. Feel free to customize my script to meet your specific needs.
Act Now
Always On VPN administrators are advised to consider solutions to automate TLS certificate enrollment and renewal as soon as possible. If your public CA of choice doesn’t support some form of certificate automation like ACME, it’s time to find another provider.
Summary
Starting in March 2026, the maximum lifetime for public TLS certificates will be reduced gradually, reaching just 47 days by March 2029. Automation will no longer be optional for Always On VPN administrators using SSTP—it will be essential. Tools like the Posh-ACME PowerShell module provide a reliable solution to streamline certificate management and ensure uninterrupted connectivity. Now is the time to prepare for this industry shift by implementing automated certificate renewal solutions. If you’d like professional assistance with this task or simply want to learn more about your options, drop me a note via the contact page, and I’ll respond with more information.
Additional Information
TLS Certificate Lifetimes Will Officially Reduce to 47 Days – DigiCert
PowerShell is an important skill for administrators supporting Microsoft workloads including DirectAccess and Always On VPN. Using PowerShell to install required roles and features is much simpler and quicker than using the Graphical User Interface (GUI), with only a single command required to accomplish this task. Some settings aren’t exposed in the GUI and can only be configured using PowerShell. In addition, PowerShell makes the task of troubleshooting DirectAccess and Always On VPN much easier.
