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GUIDES

Certificate automation, explained.

Practical guides to SSL/TLS certificates on real servers: IIS and Windows, PFX files, shorter certificate lifetimes, and choosing the right tool.

Let’s Encrypt on IIS: free SSL certificates that renew themselves

How to use free Let’s Encrypt SSL certificates on IIS and Windows Server, with automatic renewal, binding updates and checks, for one server or a load-balanced pool.

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How to automate PFX certificate renewal, password included

Renew PFX (PKCS#12) certificate files automatically: clear file names, per-certificate passwords, legacy 3DES for old Windows, bulk exports, network shares and API downloads.

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47-day SSL certificates: what changes and how to prepare

SSL/TLS certificates are limited to 200 days now, 100 days from March 2027 and 47 days from March 2029. What it means for renewals and validation, and a checklist to prepare.

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EverTLS vs Certify The Web vs win-acme

An honest comparison of three ways to automate SSL certificates on Windows and IIS: win-acme, Certify The Web and EverTLS. Prices, central management, Linux support and when to choose each.

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IIS Centralized Certificate Store with Let’s Encrypt

Use Let’s Encrypt with IIS Centralized Certificate Store: how CCS file names work, setting up the share, and renewing PFX files automatically for a whole load-balanced IIS pool.

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Wildcard SSL certificates on IIS with Let’s Encrypt

Get free Let’s Encrypt wildcard certificates on IIS and Windows Server: DNS validation with CNAME delegation or your DNS provider, automatic binding updates, and many sites on one certificate.

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Wildcard certificates with DNS-01 validation

How the ACME DNS-01 challenge works for wildcard certificates, and three ways to automate it: a DNS provider API key, a key kept on your own server, or CNAME delegation with no key at all.

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Let’s Encrypt alternatives: free ACME certificate authorities

Free alternatives and backups to Let’s Encrypt: Google Trust Services, ZeroSSL, SSL.com and Actalis compared. Wildcards, EAB setup, rate limits, and using a backup CA.

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Certbot alternatives

Alternatives to Certbot for Let’s Encrypt certificates: acme.sh, lego, Caddy, Traefik, cert-manager and win-acme, and when to manage certificates centrally across many servers.

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