The essential guide to SSL/TLS security & certificate automation (2026)

Senior cloud developer Wesley Kirkland breaks down the major SSL/TLS changes ahead and why automation is now essential for staying secure.

TechnologistsBy Wesley Kirkland2026-11-0422 mins
Two people hold an oversized gold padlock together outdoors, with one hand gripping the shackle and the other supporting the base, symbolizing shared security and trust.

SSL/TLS is one of the most fundamental and misunderstood elements of online security. It’s the bedrock of trust on the internet, protecting everything from a customer’s banking login to your personal data collected through a landing page.

SSL/TLS is no longer “set it and forget it.” The technology is mature and has been in place since 1995, though the rules and threats keep evolving. Continuous certificate management is key. With the right Certificate Authority (CA), ACME automation and process, staying secure is entirely achievable with automation.

Recently, I had the opportunity to join the urllo expert series to talk about upcoming changes to SSL/TLS. In this post, I’ll distill the key points from my session, sharing what you need to know today about SSL/TLS certificates, validation and automation.

Catch the complete discussion — including audience Q&A and live examples — in the recording embedded below, or download the slides to keep as a reference.

What is SSL? What is TLS?

SSL (Secure Sockets Layer) was the original protocol that laid the foundation, but is now obsolete. TLS (Transport Layer Security) is the modern protocol for secure web communication.

In practice, keeping your web properties secure means:

  • Preventing impersonation and fraud
  • Protecting sensitive data in transit such as your credit card details
  • Signaling to users that your site is safe to interact with

While you might remember the old green padlock or “EV” company names in browser address bars, those visual indicators have largely been deprecated. Security now happens quietly in the background, with enhanced verification via Certificate Transparency Logs and shorter certificate lifespans.

What’s the difference between SSL vs. TLS?

Most of what people call “SSL certificates” are actually TLS certificates. SSL was officially deprecated in 2015. While the terms SSL and TLS are often used interchangeably, SSL as a protocol is obsolete and certificates are officially called TLS certificates.

TLS was introduced in 1999, with TLS 1.2 (2008) still widely deployed today. TLS 1.3 introduced modern cipher suites and features such as Perfect Forward Secrecy, which generates new encryption keys for each connection made to the web server.

TLS is the modern standard, and today’s certificates follow its specification.

Who sets the rules for SSL and TLS?

The CA/Browser Forum (CA/B Forum) is the industry group that sets the rules for publicly trusted Certificate Authorities (CAs). Every public CA, from Let’s Encrypt to DigiCert, must follow the CA/B Forum standards to issue certificates.

CA/B Forum standards cover everything from how long a certificate is valid to how to complete domain control validation. These rules evolve over time, and recent changes are making automation not just recommended, but mandatory.

What is the chain of trust and how does it work?

A certificate is one link in a bigger “chain of trust.” Think of it like a tree from its trunk to its leaves:

  • Root CAs: The base of the tree and ultimate authority, used to verify other certificates.
    • Root CAs are trusted because their self-signed certificates are pre-installed in operating systems and browsers’ trusted certificate store.
    • Without Root CAs, browsers wouldn’t know which issuers to trust.
    • Root CAs are guarded closely and rarely change hands or get reissued. Compromise at this level would undermine global internet security.
    • As an additional security practice Root CAs are kept offline by their issuers with Hardware Security Modules.
    • These root CAs are negotiated and added through the CA/B Forum’s rigorous process of auditing and oversight.
    • Root CAs can only issue certificates valid up to their own expiration date.
  • Intermediate CAs: Form the trunk and branches of the tree, connecting the roots to the leaves.
    • Issued by a root CA, intermediate CAs act as secure middle managers.
    • Intermediate CAs issue certificates to others while shielding the root from exposure.
    • Additionally, Intermediate CAs can only issue certificates valid up to their own expiration date.
    • Multiple intermediate CAs can exist in a chain to provide layered security.
    • Intermediate CAs are rotated out continually to provide additional security and to avoid complex dependencies.
  • Leaf certificates: The leaves of the tree.
    • Leaf certificates are end-entity certificates that live on the servers that host websites.
    • Leaf certificates are public certificates that are presented to website visitors to make a secure connection.
    • Leaf certificates directly enable encryption between the website and the visitor’s browser.
    • Leaf certificates prove a website’s identity.
    • Browsers validate leaf certificates by following the chain up through the intermediates to the root.

When a browser connects, it verifies the entire chain from leaf to root. If any link is broken (expired, misconfigured or untrusted) users will see a warning prompting them there is danger ahead.

Which SSL/TLS certificate type should I choose?

There are many different options for organizations, depending on their size, security requirements, budget and technical capabilities. For example, smaller organizations or teams that can fully automate renewals often benefit most from single-domain certificates. Larger enterprises with complex infrastructures may choose multi-domain or wildcard certificates to simplify management through load balancers, though these bring trade-offs in visibility, risk exposure and shared key material.

The right choice balances operational efficiency, cost-effectiveness and security posture.

Certificate Type Coverage Pros Cons
Single-domain One domain or subdomain Highly secure when automated; easier to audit Only covers one domain; manual management is harder at scale
Multi-domain (SAN) Multiple domains/subdomains Consolidates management; can reduce cost Shares key material; limited to ~250 SANs
Wildcard All subdomains under one domain Cost-effective for subdomain-heavy environments Doesn’t cover apex by default; risky without tracking
Multi-wildcard Multiple domains’ wildcards Broad coverage across multiple domains Rarely needed; supported by fewer CAs

My rule and security guidance: if you can automate issuance, use single-domain certificates. Automation removes the operational burden of tracking renewals across many endpoints and ensures key material is rotated regularly, improving your security posture. Additionally, certificates issued through services AWS Certificate Manager, Azure App Service Certificates and Let’s Encrypt are typically free while maintaining all necessary security functions.

Single-domain certificates limit the blast radius if a key is compromised and are easier to manage in modern cloud environments. Wildcards and multi-domain certificates may seem convenient, but they often introduce risks like shared keys and reduced visibility over where certificates are deployed. They can also require complex configuration inventory to track certificates.

Which Certificate Authority (CA) should I choose?

Choosing the right Certificate Authority is about more than just price. It’s a strategic decision that impacts compatibility, automation options and long-term trust. Some CAs specialize in enterprise security and innovation, while others focus on accessibility and ease of integration. Here’s a comparison of some of the most widely-used and trusted CAs:

Certificate Authority Key benefits Notes
Let’s Encrypt Free, ACME-based automation Widely used; powers a large (~63%) share of the web
GoDaddy Consumer-friendly Common in small business use
DigiCert Enterprise-grade, post-quantum research Strong reputation and innovation focus
Sectigo Enterprise reputation Trusted for large-scale deployments
AWS ACM Ideal for AWS-hosted workloads Integrates with AWS services for automated management
Entrust Enterprise and government use cases Recently subject to a distrust event

Trust can change over time, so it’s important to monitor industry developments. For example, in 2024 Google Chrome announced a distrust event for nine Entrust root CAs, meaning certificates from those roots would no longer be accepted by the browser. This serves as a reminder that even long-trusted authorities can lose their status, and organizations should stay informed to avoid sudden disruptions.

What is domain control validation and how does it prove ownership?

Before issuing a certificate, CAs must verify you control the domain. These methods include but are not limited to:

  • DNS-01: Adding a TXT record to your domain’s DNS zone that contains a unique token provided by the Certificate Authority. This proves control over the domain because only someone with DNS access can add the record. Once the CA queries the public DNS and finds the correct value, validation passes. This record looks like _acme-challenge.<YOUR_DOMAIN> and is only required for the period of certificate validation.
  • HTTP-01: Placing a specific file with a unique token provided by the Certificate Authority in a well-known directory (e.g., /.well-known/acme-challenge/) on your web server. The CA will attempt to retrieve this file via HTTP (Port 80); if successful, it confirms you control the server responding for that domain.
  • Email validation: Receiving an email from the Certificate Authority sent to a pre-approved administrative address (such as admin@domain.com, webmaster@domain.com, or via your `_validation-contactemail` TXT record on the domain's APEX. ). The recipient must follow a verification link to complete the process, confirming administrative control over the domain.

Automation-friendly CAs like Let’s Encrypt use DNS-01 or HTTP-01 to make validation easier. Many will also use tools like Certbot, a free, open-source software tool that automates the process of obtaining and renewing SSL/TLS certificates from Certificate Authorities using the ACME protocol.

What’s the difference between Domain Validation, Organization Validation and Extended Validation? Which should I use?

Before choosing a certificate, it’s important to understand the three main validation levels, often referred to as the “3V’s.” These determine the verification steps a CA will perform before issuing your certificate, and they impact how your site’s identity is displayed to users.

Validation type What it verifies Encryption strength Common use cases
Domain Validation (DV) Confirms control of the domain Full encryption Most websites, blogs, redirects
Organization Validation (OV) Verifies domain control and organization details via their business registration Full encryption Business websites where identity verification matters
Extended Validation (EV) Adds the strongest verification, including individual identity verification Full encryption with highest CA warranties Banks, e-commerce, high-trust transactions

For most sites, DV is sufficient. That doesn’t mean DV certificates are less secure. DV uses the same encryption strength as OV and EV; the difference lies in the level of identity verification performed by the CA. The CA/B Forum ensures all CAs utilize the same verification processes through audits.

Determining if your organization will choose DV vs. OV vs. EV is often an organization choice. For a blog, marketing site or most business sites, DV provides the right balance of security and ease of automation. Higher validation types like OV and EV are generally reserved for organizations with regulatory, compliance or brand trust requirements, such as financial institutions or high-volume e-commerce platforms.

How can I prepare for shorter certificate lifespans?

Over the last decade, the CA/B Forum has progressively shortened certificate lifespans. Shorter certificate lifespans improve security by ensuring cryptographic materials are refreshed more often. While these changes strengthen the ecosystem, they also demand faster renewal cycles. Here’s the timeline of changes:

Year/Date Max Certificate Validity
2011 10 years
2015 3 years
2020 398 days (~13 months)
March 2026 200 days
March 2027 100 days
March 2029 47 days

In addition to shorter certificate validity periods, the CA/B Forum has also approved a major change to Domain Control Validation (DCV) lifespans: starting in March 2029, DCVs will only be valid for 10 days before they must be re-verified. This means organizations will need systems in place to revalidate domains far more frequently, adding to the operational pressure.

All of these changes, both to certificate lifespans and DCV validity, are driven by the same goal: to improve security by ensuring cryptographic materials and domain ownership proofs are refreshed more often. However, they also make manual renewal impossible at scale. Automation will be essential to avoid outages.

How can I automate SSL/TLS certificate renewals?

To keep pace with shorter certificate and DCV lifespans, you need a full understanding and inventory of your assets, as well as an automated approach to certificate management. This means setting up systems that handle the entire lifecycle: issuance, renewal, deployment and validation. All without manual intervention.

Here is my step-by-step approach to fully automate certificates.

  1. Discover and inventory all certificates across your domains and subdomains using scanning tools or scripts.
  2. Choose an ACME-compatible Certificate Authority to enable automated certificate issuance and renewal. Let’s Encrypt, DigiCert or using your cloud provider’s native tooling are all good options.
  3. Deploy an automation client like Certbot to manage the ACME protocol interactions and handle certificate requests and renewals.
  4. Integrate automation tools into your infrastructure. Connect them directly to your web server, load balancer or container orchestration platform so certificates can be renewed and hot-swapped into service without downtime.
  5. Test renewals in a staging environment to ensure configuration changes won’t break production. For example, Let’s Encrypt has a staging endpoint without API rate limits.
  6. Set up monitoring and alerts so you know if a certificate is close to expiry or if an automation job fails.
  7. Audit endpoints regularly to identify unused, expired or misconfigured certificates.
  8. Educate stakeholders so everyone understands the impact of certificate failures and the importance of automation.

In containerized or microservices environments, build automation into your CI/CD pipeline and watch for API rate limits. This is especially important during disaster recovery when multiple services may try to renew at once.

By embedding automation at every stage, you reduce the risk of outages, keep up with industry changes and free your team from repetitive manual renewals.

Which tools can make certificate management easier?

Before diving into automation and renewal processes, it’s helpful to be aware of the supporting tools that can make certificate management faster, more accurate and less prone to error. These utilities range from quick, web-based checks to powerful command-line software for in-depth management and troubleshooting.

  • crt.sh: A free, web-based Certificate Transparency log search tool that lets you look up all certificates issued for a given domain. Good when you want to monitor new or unexpected certificate issuance, detect mis-issuance or investigate phishing attempts.
  • SSLMate: Known for its “What’s My Chain Cert?” tool and CAA record generator. These help ensure your certificate chain is correctly configured and that your DNS CAA records only allow authorized CAs to issue certificates for your domain.
  • SSL Shopper: Provides easy-to-use certificate and CSR decoders, SSL installation checkers and expiration date lookups. Ideal for troubleshooting certificate errors or confirming that new deployments are set up correctly.
  • OpenSSL: A powerful, command-line cryptography toolkit used to generate keys, CSRs and certificates, as well as to inspect, convert and troubleshoot certificates. Essential when you need granular control and automation in scripts or build pipelines.
  • urllo: Our URL redirect platform automatically creates, manages and updates SSL certificates for all your configured domains. SSL certificates are automatically renewed, so your sites are always secure.

When used together, these tools give you visibility into your certificates, help troubleshoot trust chain issues, and simplify both day-to-day tasks and emergency fixes. They are a key part of a proactive SSL/TLS strategy.

Frequently asked questions about SSL/TLS certifications.

How does TLS encryption work?

TLS encryption works by creating a secure, encrypted connection between a user’s browser and a web server so that data can’t be read or tampered with by others. Here’s how it works in simple steps:

  1. The browser says hello.
    When you visit a site, your browser sends a “Client Hello” message that includes supported encryption methods.
  2. The server responds with its identity.
    The server sends back a “Server Hello” plus its TLS certificate, which contains its public key and is verified by a Certificate Authority.
  3. The browser checks the certificate.
    If the certificate is valid and trusted, the browser continues. If not, you see a security warning.
  4. A session key is created.
    The browser generates a one-time symmetric key (fast for encrypting data) and encrypts it using the server’s public key so only the server can decrypt it.
  5. Secure connection established.
    Both sides now share the same session key. All data sent between them is encrypted, preventing eavesdropping or tampering.

In short: TLS uses public-key cryptography to securely exchange a shared secret, then uses that secret to encrypt everything sent during the session.

What is a TLS handshake?

A TLS handshake is the process your browser and a server go through to establish a secure, encrypted connection before any data is exchanged.

The browser and server agree on encryption, verify identity and establish shared keys for secure communication.

It’s the negotiation phase that sets the rules for the session.

What is a cipher suite?

A cipher suite is a set of encryption algorithms that a browser and server use to secure a TLS connection. It defines how data will be encrypted, authenticated and protected during the session. Here’s what it includes:

  1. Key exchange method.
    Determines how the shared secret (session key) is securely created, e.g., ECDHE or RSA.
  2. Authentication algorithm.
    Verifies the server’s identity using its TLS certificate.
  3. Encryption algorithm.
    Protects the data being transmitted, e.g., AES-GCM or ChaCha20.
  4. Message integrity algorithm.
    Ensures data hasn’t been changed in transit, often provided as part of modern AEAD encryption modes.

In short: A cipher suite is the recipe of cryptographic tools used during a TLS session, telling the browser and server exactly how to secure the connection.

What happens if my certificate expires?

If your TLS/SSL certificate expires, browsers will no longer trust your website and visitors will see a full-page security warning instead of your site. Here’s what that means:

  1. Browsers block the connection.
    Users will see messages like “Your connection is not private” or “Security certificate has expired.”
  2. Most visitors won’t proceed.
    Modern browsers make it difficult (and scary) to bypass the warning, causing most users to leave immediately.
  3. Search engines may react.
    Google can reduce visibility for insecure sites, and Chrome may label the site as “Not Secure.”
  4. APIs, apps and integrations may break.
    Anything relying on HTTPS, webhooks, mobile apps and third-party services may stop working.
  5. Your site becomes vulnerable.
    Without a valid certificate, data is no longer encrypted or authenticated, increasing security risks.

In short: An expired certificate makes your site unsafe to users and unusable for many services. Renewing it immediately restores trust and secure access.

Why does my certificate say "not trusted" even though it's valid?

A certificate can show “not trusted” even when it’s valid because something in the trust chain, configuration or browser environment is incorrect. Here are the most common reasons:

  1. Missing intermediate certificates.
    If the server isn’t sending the full certificate chain, browsers can’t verify the link between your certificate and the root authority.
  2. Wrong domain name (hostname mismatch).
    The certificate must match the exact domain the user is visiting (including subdomains like www vs. non-www).
  3. Untrusted Certificate Authority (CA).
    The certificate was issued by a CA that isn’t in the browser’s trusted root store, common with private, internal or self-signed certs.
  4. Outdated device or browser.
    Older systems may not recognize newer root certificates, causing trust errors even for fully valid certs.
  5. Mixed HTTP/HTTPS resources.
    If secure pages pull in insecure content or scripts, some browsers show warnings that resemble trust issues.

In short: A certificate can appear “not trusted” when the browser can’t verify the certificate chain, the domain doesn’t match or the user’s system doesn’t trust the issuing authority, even if the certificate itself hasn’t expired.

Two people hold an oversized gold padlock together outdoors, with one hand gripping the shackle and the other supporting the base, symbolizing shared security and trust.

By Wesley Kirkland

Senior Cloud Development & DevOps Engineer

Wesley Kirkland is a seasoned cloud and DevOps specialist with expertise in AWS, CI/CD pipelines, containerization, security research and large-scale web infrastructure. He regularly speaks on SSL/TLS, cloud security and automation to technical audiences.

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