The Essential Guide to Testing Your Website‘s SSL/TLS Security

SSL/TLS encryption is the backbone of secure internet communications. Yet data around website attacks shows thousands still get compromised yearly due to vulnerable SSL/TLS implementation.

Stay compliant and ensure your organization‘s sensitive customer data is truly protected against the sophisticated threats of today. Read this expert guide to discover and harden any deficiencies using 17+ handy online tools purpose-built for SSL/TLS security auditing.

SSL/TLS: Foundational Website Data Protection Under Threat

SSL, also known as TLS, establishes secure, encrypted channels of communication critical for defending against cyber-crime and espionage.

Via "handshake" exchanges involving digital certificates, SSL/TLS enables trusted connections where data gets transmitted safely without risk of prying eyes intercepting it.

SSL/TLS also proves website validity so users can confirm they’re interacting with legitimate sites, not spoofed imposters attempting theft or fraud.

Yet despite its security superpowers, this vital protocol remains susceptible in today‘s threat landscape. Consider:

  • Over 15.5 million website attacks occurred in 2021, per security company Akamai

  • Of data breaches studied in 2021, the OWASP Foundation found over three-quarters involved application-layer attacks which SSL/TLS directly counters

  • At least 10% of websites still run insecure SSL/TLS protocols or weak ciphers outlawed years ago, giving threat actors openings to exploit (source)

Clearly, defenders must remain persistent to stay ahead of attackers constantly poking for flaws in SSL/TLS implementations.

Common SSL/TLS Vulnerabilities and Misconfigurations

Website owners tend to "set and forget" their SSL/TLS certification and configuration when first enabling HTTPS—a risky approach.

Problems frequently encountered include:

Expired or invalid certificates causing sites to revert back to insecure HTTP

Weak cipher suites using older or insecure cryptographic algorithms

Unsupported legacy protocols like SSLv2/v3 and TLS 1.0/1.1 leaving sites susceptible to attacks

Mismatched hostnames confusing browsers and raising warnings

Incorrect chain of trust path errors neutralizing encryption

Mixed HTTP/HTTPS content opening exploits through unencrypted requests

❌ Dangerous published vulnerabilities like Heartbleed, DROWN, FREAK, Logjam, etc

Staying on top of all this complexity is difficult without the right tools…which brings us to our next section!

17+ Handy Online Tools for Automated Testing of SSL/TLS Security

Manually testing and monitoring numerous aspects of SSL/TLS security is unrealistic.

Thankfully, specialized tools in recent years have emerged to自动化 analyze configurations, scan for flaws, and highlight vulnerabilities needing urgent attention.

We‘ve thoroughly evaluated 17+ of the best online testing tools available in 2023 based on criteria like:

✅ Depth and breadth of analysis

✅ Accuracy of results

✅Ease of use for technicians and non-experts alike

✅ Ability to detect the most up-to-date threats

So without any further ado, let‘s dive in!

SSL Server Test – SSL Labs

1. SSL Server Test

There‘s no better free tool than SSL Labs for comprehensive testing and risk assessment. Offering A-F letter grade ratings measuring over 200+ parameters, few stones go unturned identifying configuration issues.

Key details checked:

✓ Supported protocols and ciphers
✓ Certificate validity, keys, signatures, expiration
✓ Vulnerabilities like Heartbleed, FREAK, POODLE, etc
✓ Forward secrecy & perfect forward secrecy support
✓ Renegotiation support
✓ Trustworthiness of certification authority

We appreciate how SSL Labs delivers technical rigor sought by cybersecurity professionals while also keeping things accessible for website owners less familiar with cryptographic principles and acronyms!

SSL Checker – The SSL Store

2. SSL Checker – The SSL Store

When you just need a quick second opinion confirming your SSL/TLS implementation checks out, this handy tool from The SSL Store nicely fits the bill.

It validates in seconds:

✓ Certificate properly issued
✓ Expiration date OK
✓ Trust path intact
✓ Hostname matches cert

For the layperson, it delivers easy assurance everything looks good or early warning of specifics that seem off warranting further investigation.

Other useful offerings from The SSL Store helping administrators inspect certification details:

TLS Test – DomSignal

3. TLS Test – DomSignal

Quickly determines your servers‘ supported TLS protocols—ideal for confirming modern versions like TLS 1.3 are in place and legacy SSL is disabled.

Additional TLS & SSL capabilities inspected:

✓ Certificate validity
✓ SSL errors present (if any)
✓ Vulnerabilities scan
✓ Server preferences & cipher suites
✓ Key exchanges & asymmetric algorithms
✓ Bulk encryption algorithms

Summary and detailed technical breakdown facilitates identifying exact protocols and ciphers to disable or further strengthen.

DomSignal’s general SSL Scanner also fantastic for finding common misconfigurations.

Certificate Inspector – Mozilla Observatory

4. Certificate Inspector – Mozilla Observatory

Open-source tool powered by Mozilla scans sites on multiple factors influencing SSL/TLS security.

Alongside assessing server configuration and supported ciphers, we especially appreciate how Observatory focuses on the certificate itself—the core foundation enabling trusted encryption.

Key certificate properties examined:

✓ Validation & trust path
✓ Expiration date
✓ Hostname match
✓ Issuing authority

Helps identify errors like expired certs as well as inspect automation readiness for renewals.

Mozilla Observatory incorporates additional security header and web vulnerability testing also useful from a comprehensive SSL/TLS hygiene perspective.

Vulnerability Scanner – Wormly

5. Vulnerability Scanner – Wormly

If you’re looking to specifically home in on dangerous published vulnerabilities frequently targeting SSL/TLS implementations, Wormly‘s got your back.

It automatically screens for dozens of risks like:

❗️Heartbleed
❗️POODLE
❗️FREAK
❗️BREACH
❗️LOGJAM
❗️BEAST
❗️LUCKY13

These can cripple encryption protections if left unaddressed.

Wormly also examines related metrics like certificate validity period, key exchange methods, bulk ciphers, and message authentication to provide expand context around the risk profile.

Security Headers Analyzer – CryptCheck

6. Security Headers Analyzer – CryptCheck

Hardening HTTP security headers represents another “quick win” websites should prioritize to augment protections enabled by SSL/TLS.

CryptCheck makes this easy by testing for proper implementation of headers like:

🔒HSTS (HTTP Strict Transport Security)
🔒CSP (Content-Security Policy)
🔒X-Frame-Options
🔒X-XSS-Protection

These instruct browsers to force encryption, restrict resource loading, and tighten settings to deflect attacks like XSS and clickjacking.

Get peace of mind your web server sends the right instructions to clients for reinforced security—or promptly fix any missing headers CryptCheck highlights.

Cipher Suite Scanner – DigiCert

7. Cipher Suite Scanner – DigiCert

When hardening environments against sophisticated threats, details like cipher suite selection separating secure implementations from vulnerable ones.

DigiCert SSL Analyzer detects weak, insecure ciphers flagged by organizations like OWASP and Mozilla Foundation as risks to disable.

Conversely, you can validate supporting modern ciphers offering robust encryption through mechanisms like elliptic curve cryptography:

✅TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384
✅TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384

Taking stock of your current cipher suite configuration is wise to identify priority areas needing upgrade.

DigiCert’s scanner also examines related metrics like certificate and protocol support for helpful wider context.

Zero-Day Threat Scanner – ImmuniWeb

8. Zero-Day Threat Scanner – ImmuniWeb ☢️

Most SSL/TLS testing tools focus narrowly on encryption analysis. Yet breaches often involve complementary vulnerabilities allowing bad actors initial access to infiltrate deeper internally.

That‘s why we recommend integrating ImmuniWeb‘s free checks for over 1500 web security risks across:

🔎Suspicious application components
🔎Outdated web servers
🔎Insecure access controls
🔎Exposed private data
🔎Plaintext passwords

These wider website risk factors can undermine SSL/TLS protections once the outer barriers get bypassed, enabling lateral movement.

Internal Server Scanner – Nmap

9. Internal Server Scanner – Nmap

Most online scanners analyze sites from outside. Nmap takes an inside-out approach inspecting encryption protocols and certificates across internal networks.

What makes Nmap special?

⚡️Fast batch scanning of multiple hosts
⚡️Custom scripts for advanced TLS debugging
⚡️Windows, Linux, macOS, and UNIX support
⚡️Free and open source

If you manage infrastructure internally, leverage Nmap to rapidly audit network-wide SSL/TLS health checks. Grant your cybersecurity team powerful diagnostics for harder to detect issues.

Client Capability Checker – HowsMySSL

10. Client Capability Checker – How‘s My SSL
✅ Most tools focus on server-side configuration only.

How‘s My SSL smartly evaluates the other half of the equation—client-supported parameters.

It detects browser/device specifics like:

🧑‍💻 Supported TLS protocols
🧑‍💻 Ciphers enabled
🧑‍💻 Compression compatibility
🧑‍💻 WebCrypto support

Uncover user experience impacting quirks causing communications breakdowns between servers and clients.

Certificate Evaluator – SSLChecker

11. Certificate Evaluator – SSLChecker

Need a straightforward second opinion on your certificate‘s implementation status?

SSLChecker checks all the key fundamentals:

🔍Certificate issuer & expiration
🔍Overall grade
🔍SSL errors present (if any)
🔍Chain of trust validation

Concise results provide website owners, marketers and others less technically versed confidence in their site‘s encryption protections.

Automated expiry alerts also help avoid disruption from expired certificates.

Crowdsourced Security Audits – Observatory by Mozilla

12. Crowdsourced Security Audits – Observatory by Mozilla

Mentioned earlier for its certificate inspection, Mozilla Observatory uniquely incorporates trusted analysis from leading tools:

🔎 SSL Labs – Grades server config
🔎 ImmuniWeb – Detects web app vulnerabilities
🔎 HSTS Preload – Checks Strict Transport Security
🔎 CryptCheck – Analyzes security headers

Blending these comprehensive audits into one dashboard gives tremendous visibility into SSL/TLS health.

Open-source transparency also means methodology and fault detections improve over time.

Protocol & Cipher Inspector – TestSSL.sh

13. Protocol & Cipher Inspector – testssl.sh

Like to tinker under the encryption hood? testssl.sh delivers insight into granular protocol and cipher details.

🔍Handshake simulation
🔍Certificate public key bits
🔍Asymmetric algorithms
🔍Key exchanges & outflows
🔍Message authentication
🔍Zero RTT support

Output mirrors the technical terminology true security practitioners understand. Terrific SSL/TLS learning companion for admins and ethical hackers alike.

Vulnerability Trends Tracker – Censys Search Engine

14. Vulnerability Trends Tracker – Censys Search Engine

Censys allows live searching of the entire IPv4 internet space on various attributes.

This enables researchers to analyze macro encryption trends and quickly quantify prevalence of SSL/TLS vulnerabilities at scale.

For example, searching certificates for signature algorithms flagged as weak like SHA-1 reveals ~25% still actively use it.

Powerful visibility bolsters risk visibility. Censys works directly with US Department of Homeland Security to uncover and protect against threats globally.

DDoS Resistance Inspector – Web Stress Test

15. DDoS Resistance Inspector – Web Stress Test

While testing SSL/TLS configuration checks the data protection element, websites must also confirm satisfactory uptime performance.

Uses open-source tools to safely simulate high traffic loads mimicking DDoS bombardment campaigns.

This proactively uncovers:

☣️ Infrastructure bottlenecks
☣️ Application crashing points
☣️ Encryption communication limits

Hard to defend against attacks when you don’t know your site’s true capacity limits beforehand!

CORS Misconfiguration Scanner

16. CORS Misconfiguration Scanner – TLS Observatory

Properly configured CORS settings are mandatory for preventing unauthorized cross-domain data transfers many web apps facilitate.

This scanner detects faulty CORS implementation enabling CSRF attacks to exploit session cookies, authentication tokens, and sensitive data.

👓Inspects for checks like:

🔎Overly permissive origins
🔎Lacking credentials flag
🔎Exposed methods and headers

Much easier fixing issues proactively vs after a breach!

Password Brute-Forcer – SSLyze

17. Password Brute-Forcer – SSLyze

Last but not least, SSLyze demonstrates how client-authentication encryption (used in VPNs, outlook web access etc) succumbs to basic password guessing.

It brute forces logins amplified through concurrently sent requests leveraging Python multiprocessing.

A reminder that robust TLS means little without prudent access controls in place!

Keep Your Security Handshake Intact

This concludes our recommendations for 17+ capable tools delivering automated SSL/TLS auditing to suit a variety of expertise levels and testing appetites.

Getting clear visibility into potential chinks in your site‘s cryptographic armor is key preventing data pilfering. Don‘t allow inertia to erode once sturdy HTTPS protections now full of holes!

Many defects take only minutes to detect and remediate when you know exactly where to focus upgrades using these trusty web diagnostics platforms.

While no guide can guarantee stopping all contemporary threats as they continue evolving, we hope these practical tips better empower your organization maintaining credible SSL/TLS hygiene and due diligence against unfortunate headlines about tomorrow‘s inevitable mega-breach!