If you manage websites, outages caused by SSL/TLS problems can completely devastate traffic and revenue. My goal here is to comprehensively equip you with powerful free tools to quickly troubleshoot these pesky issues.
By the end, you‘ll have practical solutions to confidently diagnose SSL/TLS vulnerabilities, misconfigurations, certificate problems and more – before they interrupt your site‘s availability!
We‘ll uncover:
- Common SSL/TLS pitfalls that impact webmasters
- 11 capable troubleshooting tools in detail
- Head-to-head comparisons between tools
- Smart ways to leverage these utilities day-to-day
- How these tools fit into broader security strategy
First, let‘s quickly level-set on the prevalence of SSL/TLS problems…
The Scale of SSL/TLS Issues Facing Webmasters
SSL/TLS is implemented for 80%+ of all internet traffic to provide encrypted transport security.
But glitches still abound:
- 23.5% of web servers use insecure SSLv3 or earlier protocols
- 33% still have certificates expiring in less than a year
- 10-20% have misconfigured chains invalidating trust
Costs of outages from these problems average $250,000 per hour across industries!
Catching issues proactively with scanning tools is vastly preferable to interruptions or data breaches.
Next we‘ll explore your new troubleshooting toolkit…
DeepViolet Assists Internal SSL/TLS Auditing
DeepViolet is an invaluable open source Java tool for inspecting SSL/TLS configurations on internal systems.
It performs deep protocol analysis checking for:
✅ Weak/insecure ciphers
✅ Invalid certificate chains
✅ Revoked/expired certificates
✅ And more…
DeepViolet generates easy to interpret textual reports describing all vulnerabilities found.
For embedded systems, intranets and private networks, DeepViolet is a must-have to identify insecure settings before exploitation.
Pro Tip: Schedule scans with Jenkins to continually validate proper SSL/TLS hygiene internally.
SSL Diagnos Provides Rapid External Testing
Need a quick check of live production systems without deeper scanning?
SSL Diagnos examines external-facing setups supporting HTTPS, SMTP, FTPS.
In seconds, it delivers simple letter grade ratings across:
✅ Certificate validity
✅ Protocols
✅ Ciphers
✅ Specific flaws like HeartBleed!
When issues arise, rapidly rule out SSL/TLS as the culprit with SSL Diagnos before diving deeper.
Handy Hint: Integrate SSL Diagnos into network monitoring dashboards to watch certificates approaching expiration.
Start Automated Testing with SSLyze
SSLyze is likely the most popular cross-platform Python scanner used by webmasters today.
It installs locally to test remote configs checking:
➕ Certificate contents
➕ Cipher strength
➕ Protocol support
➕ Vulnerabilities like FREAK, Logjam, and more
Flexible connectivity options and automated output formats like JSON integrate nicely with CI/CD pipelines.
If you manage multiple sites, SSLyze delivers easy automation to verify security across all your properties.
Pro Tip: For additional visibility, output SSLyze results into monitoring tools like Splunk or Elasticsearch.
OpenSSL Provides Crypto Toolkit for SSL/TLS Management
OpenSSL furnishes ubiquitous cryptographic algorithms and protocols on practically every server platform.
For webmasters, it empowers directly:
🔏 Testing ciphers & protocols
🔏 Decoding certificate contents
🔏 Converting certificate formats like PEM, DER, P7B
🔏 Revoking/renewing local certs
Many SSL/TLS scanners actually utilize OpenSSL underneath to perform scans.
Familiarity with OpenSSL pays dividends when debugging and architecting robust solutions.
Handy Hint: Create scheduled OpenSSL scripts across web assets to warn of expiring certificates ahead of outages.
Uncover Hidden Internal Risks with SSL Labs Scan
SSL Labs Scan delivers Qualys SSL Labs trusted testing via command line for internal systems.
Benefits include:
✅ Respected Qualys scan engine
✅ Automatable API testing
✅ Detailed JSON output
✅ Flexible connectivity testing
Discovering rogue devices on networks disregarding security standards is unfortunately common. SSL Labs Scan is the tool to quickly find them!
Schedule scans with Jenkins against subnet ranges to uncover these hidden internal risks early.
Rapid Risk Identification with SSL Scan
SSL Scan lives up to its name by swiftly detecting high severity SSL/TLS misconfigurations.
It shines bright finding:
✅ Deprecated SSLv2/SSLv3 protocols
✅ Weak/insecure ciphers
✅ Cert problems invalidating identity
✅ Common flaws like Heartbleed
SSL Scan produces concise, parser-friendly output perfect for automation. Effortlessly establish baseline security hygiene across devices with SSL Scan‘s speed.
Pro Tip: For troubleshooting, first use SSL Scan to identify issues for investigation before deeper scanning.
Geekflare Scanner API Checks Certificates & Configuration
The Geekflare Scanner API furnishes a simple programmatic interface to check SSL/TLS security posture.
It validates:
➕ Certificate contents & validity
➕ Protocol support
➕ Ciphers in use
➕ Key infrastructure
Flexible JSON output integrates nicely into other tooling for monitoring and auditing.
For developers, the API simplifies adding SSL/TLS testing into applications. Schedule scans over time to track resolution of discovered problems.
Start In-Depth Testing with TestSSL.sh
When simplistic scanning reveals issues, it‘s time to break out comprehensive, meticulous TestSSL.sh.
It audits SSL/TLS supporting an astounding variety of technologies:
🔐 Web servers
🔐 Email servers
🔐 Database servers
🔐 LDAP
🔐 MQTT
🔐 And more…
Beyond SSL/TLS, it uncovers misconfigurations across cipher choices, key exchanges, crypto algorithms and protocol versions.
TestSSL.sh leaves no stone unturned illuminating security posture via enormously detailed text output. Its breadth and depth of coverage is incredible.
If you have the skills, configuring Docker or Jenkins to automate TestSSL testing hardens environments tremendously.
Automated TLS Security Testing with TLS Scan
TLS Scan focuses on protocol & cipher evaluation across multiple technologies:
➕ Mail servers
➕ Databases
➕ Web apps
➕ Mobile
It performs coordinated, automated handshakes using different protocol versions, cipher suites, key exchanges and algorithms.
This reveals precisely which secure configurations succeed verses fail when connecting vulnerabilities and misconfigurations.
JSON output neatly packages results for further analysis. The custom retry logic also helps avoid transient network flakes.
Cipher Suite Scanning Simplified
CipherScan furnishes an easy method to check HTTPS cipher configuration.
In seconds, it reports:
✅ All ciphers offered by a server
✅ Any insecure ciphers supported
✅ Their priority order
✅ SSL Labs letter grade
Having visibility to configured suites is critical for diagnosing connectivity issues as well as purging old insecure algorithms.
CipherScan neatly accomplishes this goal while avoiding unnecessary complexity. Sometimes simple tools are best!
SSL Audit Checks Best Practice Compliance
SSL Audit enjoys longevity having provided no-cost, standards-focused auditing of SSL/TLS security policies for over a decade.
It evaluates servers against better practice recommendations including:
➕ Protocols
➕ Ciphers
➕ Certificate contents
➕ Trust validation
➕ Vulnerabilities
Succinct text output delivers key high-level information without superfluous detail.
Periodic SSL Audit testing demonstrates proper due diligence across assets against security best practices.
Comparing Tools by Capability and Use Case
With so many utilities covered, you may wonder which to use when. Here‘s a capability matrix comparing tools:
| Tool | Auto Tests | JSON Output | Web App Scanning | Email Servers | Code Library |
|---|---|---|---|---|---|
| DeepViolet | ✅ | ✅ | |||
| SSL Diagnos | ✅ | ✅ | ✅ | ||
| SSLyze | ✅ | ✅ | ✅ | ✅ | |
| OpenSSL | ✅ | ✅ | |||
| SSL Labs Scan | ✅ | ✅ | ✅ | ||
| SSL Scan | ✅ | ✅ | ✅ | ||
| Geekflare Scanner | ✅ | ✅ | ✅ | ||
| TestSSL.sh | ✅ | ✅ | |||
| TLS Scan | ✅ | ✅ | ✅ | ✅ | |
| Cipher Scan | ✅ | ✅ | ✅ | ||
| SSL Audit | ✅ |
And common use cases where they excel:
- Internal/Intranet: DeepViolet
- Code Libraries: SSLyze
- Automatable: SSL Scan
- Encryption Ops: OpenSSL
- Mail Servers: TestSSL.sh
- APIs: Geekflare Scanner
- CI/CD Pipelines: SSLyze
- Developers: Geekflare Scanner
Understanding tools‘ strengths guides utilizing the proper utility at the right time.
Architecting SSL/TLS Security In Layers
Beyond standalone operation, crafting defense-in-depth using combinations of tools maximizes risk reduction.
Here‘s an example tiered strategy:
Monitoring – Health checks with SSL Diagnos
Automated Testing – Daily TLS Scan evaluations
Code Libraries – Enabling SSLyze in apps
Manual Verification – Impromptu TestSSL.sh audits
Wildcard Assessment – Regular OpenSSL network cipher tests
Distributing robustness across diverse, layered solutions provides resilience. Each tier fills potential gaps of others.
Conclusion
I hope mapping out both high-level and specialty SSL/TLS troubleshooting tools against common needs equips you to competently combat issues as a webmaster.
Remember also to architect robust, redundant checking in layers for critical systems. Don‘t wait for outages before verifying security!
Please drop any questions below in comments and I‘m happy to help further. Here‘s to reliable, secure websites!
