Automating Let’s Encrypt SSL certificates on Windows is best achieved using Certify The Web, a powerful graphical ACME client that completely eliminates manual certificate renewals. While Let’s Encrypt revolutionized web security by offering free SSL/TLS certificates, its 90-day certificate lifespan demands a robust automation strategy to prevent sudden website downtime.
This guide details how to install, configure, and automate Let’s Encrypt certificates using Certify Certificate Manager. Prerequisites Before Setup Ensure you meet these requirements before continuing:
Windows Server: Operating system running Internet Information Services (IIS) or another hosted web service.
Public DNS Control: A registered domain name mapping correctly to your server’s public IP address.
Network Permissions: Firewall rules allowing inbound traffic on Port 80 (for HTTP validation) or Port 53 (for DNS validation). Step 1: Install Certify The Web
Download the latest installer directly from the Certify The Web Official Download Page.
Right-click the installer executable and select Run as Administrator.
Follow the installation wizard steps, accept the license terms, and retain the default installation path. Launch the application once installation finishes. Step 2: Register an ACME Contact Account
Upon your first launch, click New Certificate in the top left corner.
A prompt will appear asking for a primary contact email address.
Input your email address, check the agreement box, and select Register Contact.
This links your server to the Let’s Encrypt ACME API to receive automated configuration alerts. Step 3: Configure Your First Managed Certificate 1. Add Certificate Domains
Name your managed certificate profile something recognizable (e.g., “Main Production IIS”).
In the Select Website dropdown menu, pick your target site (e.g., “Default Web Site”).
The app automatically parses existing IIS bindings, or you can manually enter your Fully Qualified Domain Name (FQDN) into the Add domains to certificate box and click Add Domains. 2. Configure Domain Authorization
You must choose one validation method to prove you control the domain:
How would I create a cert that will work for this situation?
Then get and apply your certificate to the site using Certify Certificate Manager :click New Certificate, Select your IIS site, Certify The Web
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