Don’t Let Your Website Go Dark: 14 Tools to Monitor SSL Certificate Expiry

Have you ever encountered dire warnings while browsing websites – telling you the connection is not private or your data may get stolen? Chances are the site‘s SSL certificates have expired or become invalid. Left unaddressed, this spells doom not just for security but business continuity too.

As an ethical hacker who regularly tests corporate web infrastructure, I cannot emphasize enough the criticality of staying on top of certificate lifecycles. In this comprehensive guide, let me expand your awareness of the risks posed by expired certificates and how specialized monitoring tools can provide an early warning system.

Why Website Owners Can’t Ignore SSL Certificates

SSL certificates form the backbone of secure websites. By enabling data encryption and validating website identity, they facilitate sensitive transactions and build user trust.

But much like magicians, these certificates have a limited lifespan. As an expiry date inevitably approaches, the protection vanishes leaving websites exposed like a sitting duck.

No longer trusted by browsers, user warnings exacerbate matters. Visits drop drastically. Online revenue dries up. Reputation takes a hit. Not the ideal outcomes for businesses depending on their site!

To quantify the impact, research shows that 61% of consumers will not return to a site showing SSL warnings while 59% hesitant to provide personal or payment data. That translates to a huge chunk of visitors gone instantly!

For e-commerce companies, the blow can run into 1000s of dollars in lost sales – accelerated if occurring on Cyber Monday. Plus dealing with the barrage of customer complaints and tech support calls afterwards.

But it‘s not just sales. Expired certificates open avenues for hackers to launch man-in-the-middle attacks and steal sensitive user data. They can also distribute malware taking advantage of invalid HTTPS protection.

Clearly you need controls in place to renew certificates automatically before expiry ever threatens availability or security.

That‘s not all. SSL validity also depends on factors like the full certificate chain being trusted and the intermediate issuing authority remaining endorsed. Revocation lists can instantly nullify active certificates as well.

Manually tracking these multiple aspects across infrastructure scales from complex to impossible. Drop the ball once and it can snowball into catastrophe.

This guide explores specialized monitoring systems explicitly designed to issue expiry and other critical alerts around the lifecycle of SSL certificates. Let‘s first categorize the spectrum of options available.

Categories of SSL Monitoring Tools

Paid Monitoring Services

  • Full-featured but premium offerings from established vendors like Digicert, SSL.com etc
  • Centralized tracking across unlimited domains and certificates
  • Advanced capabilities for enterprises e.gtwo-factor authentication, role based access
  • Integrations with existing monitoring and ITSM stacks
  • Higher pricing but some offer free trials

Freemium Monitoring Tools

  • Generally simple products focused purely on expiration alerts
  • Free tier for basic functionality but with limits on domains
  • Primarily self-serve model with email-based support
  • Meet basic business use cases affordably
  • Scaled plans open up more sophisticated capabilities

Open Source Monitoring Projects

  • Shared publicly for community benefit by developers
  • Implementation requires more technical expertise
  • Highly customizable to specific infra needs
  • No vendor dependencies or usage costs
  • Limited documentation and access to support

Monitoring Suite Integrations

  • Plugins that hook into broader metrics solutions
  • Present certificate expiry as another observable metric
  • Leverage existing dashboarding, visualization capabilities
  • Complement overall infrastructure reliability goals
  • Require managing additional moving pieces

The categories cover a spectrum allowing both individuals as well as big corporations to find options matching their scale, technical needs and budgets.

Within these, here are 14 versatile SSL monitoring tools worth evaluating further.

14 Feature-Packed Tools to Monitor SSL Certificates

1. SolarWinds Web Help Desk (Paid Service)

Trusted by 100,000+ IT teams globally, Solarwinds Web Help Desk provides extensive SSL certificate tracking as part of its integrated support ticketing capabilities.

One dashboard tracks expiry across domains while allowing collaboration between technical and non-technical teams to streamline renewal. Monitoring background processes validate full certificate chains too identifying problems before they cause customer-impacting issues.

While packed with features, for many the investment may only make sense at larger scale. But with a solid foundation of meeting complex enterprise security and compliance needs, a closer look is certainly merited especially if already using other SolarWinds tools.

2. SSLMate (Freemium Service)

SSLMate focuses explicitly on certificate management – selling them, automating issuance and notifications around renewals. Public CertSpotter integration allows even free users to get notified of expiry dates. For peace of mind, opt for paid plans starting at $15 per month and let their experts handle all aspects certificate procurement and life cycle.

3. HealthChecks (Open Source)

Part of the Healthchecks.io family of open source status page projects, HC SSL Monitor offers self-hosted certificate expiration monitoring. Being Python-based, it can integrate nicely into cloud and container environments. Code modifications possible to tailor notifications and checks to specific needs.

4. SSL Certificate Monitor (Paid Service)

SSL Certificate Monitor from SSLShopper provides max visibility into certificate statuses across domains via a central dashboard tracking expiry dates, removals from trust stores, upcoming releases of browser versions and more. Stay on top of the latest TLS news with digest emails as well. Free 30 day trial provided.

5. ThousandEyes (Monitoring Suite)

Part of its digital experience monitoring suite, ThousandEyes utilizs a vast global sensor network to track SSL certificate statuses across web infrastructure and ISPs. Integrates expiry information into broader views of site delivery and performance metrics helping ops teams correlate issues. Enterprise focused but offers free trial for proof of value.

6. Comodo (Paid Service)

As a top certificate authority, Comodo offers both free and paid certificate monitoring to safeguard websites secured by certificates they have issued. Configurable expiry notifications help avoid outages. For utmost peace of mind, opt into their warranty package which guarantees certificate renewals and up to $250k website security breach insurance.

7. Monitis (Paid Service)

The March 2022 Netcraft survey found 37% of phishing sites abuse expired or self-signed SSL certificates to still seem legitimate. Monitis can help avoid being in that dreaded list using expiration monitoring coupled with periodic reputation scans powered by their global sensor network. Plans from $20/month.

8. SSL Cert World (Freemium)

Minimalistic and affordable, SSL Cert World focuses purely on fundamentals – notifies globally before expiries and confirms renewals. Free plan supports 1 domain while $14/year unlocks 20. Support direct, no complex dashboards. For many sites with just a few externally visible certificates, hits the spot.

9. CAB Forum BA Browser (Open Source)

Trusted by certificate authorities globally to validate website certificates, the automated CAB Forum CAB Browser app allows self-hosting these checks too. While command line based and technical to operate, offers peace of mind that public CAs apply to your domains. Available freely.

10. SSLMate Crom (Monitoring Suite)

Crom focuses on metrics and observability. This Go app exposes key SSL/TLS server attributes as Prometheus metrics – including expiry details. Useful for developers and SREs to incorporate into Grafana dashboard for unified infra visibility. Promoted by the SSLMate team but open source and extensible.

11. Norton (Paid Service)

The household name in antivirus software also provides website security capabilities like malware detection, reputation monitoring and SSL validation. Norton notifies automatically if your certificates are expiring or improperly issued helping maintain visibility and control. Requires a paid subscription.

12. SSL Visibility (Paid Service)

Part of Comodo’s enterprise offerings, SSL Visibility delivers certificate health monitoring combining insights from their global sensor network with machine learning algorithms trained on a mammoth certification data set. Graphical cyber hygiene reports simplify tracking infrastructure security posture.

13. SSL Certificate Checker (Open Source)

This handy OpenSSL based checker runs on Linux servers scanning certificates and alerting on ones expiring shortly or having validation issues. Being open source allows tweakability to custom infra needs. Foradmins managing numerous multi-domain certs across websites, saves effort.

14. BlackCert (Open Source)

A recent addition from last month, BlackCert takes an adversarial approach to help blue teams proactively identify weak certificates in their perimeter via oath token authentication enabled scans. Beyond just expiry, provides assurance testing wildcard support, signature algorithms etc.

The diverse tools showcase evolutions happening in simplifying previously arduous SSL monitoring – whether via SaaS offerings or programmatic integrations or community shared projects.

Making use of them is the first step to troubleshooting certificates proactively and maintaining continuity of secure encrypted browsing experiences for customers.

Evaluating Tools for Effective Monitoring

With myriad options available, how do you approach the analysis to determine what fits best? Use these parameters around capabilities, integrations, implementation and pricing as a structure:

Monitoring Scope

  • Expiry Tracking – Days left notifications
  • Revocation Checking – Against trusted lists
  • Validation Testing – All domains on certificate
  • Error Detection – Warnings from browsers
  • Protocol Checks – TLS 1.3, TLS 1.2 etc
  • Certificate Insights – Age, signature algorithm used etc

Alert Mechanisms

  • Email Notifications – For technical teams
  • SMS Messages – Business stakeholders
  • In-app Notifications – Dashboard visibility
  • Chatbot Integration – Interactive queries

Domain Coverage

  • Single Site – Small business focus
  • Multi-Site – For established companies
  • Wildcards Certs – Handle subdomain setups
  • Discovery Support – Defaults from server
  • Bulk Upload – Simplify large infra

Reporting

  • Expiry Date Listing – Across certificates
  • Changes Feed – Newly detected certs
  • API Access – For custom integration
  • Dashboard – Centralized visibility
  • Audit Logs – Filtering to specifics

Security

  • Encryption – Certs and keys at rest
  • Access Controls – Isolation options
  • Activity Audit – Deter modifications
  • Incident Options – Breach insurance

Pricing

  • Free Plan – Limits on domains
  • Per Domain Costing
  • Volume Discounts
  • Free Trial – Demo capabilities
  • Integrations – Associated pricing

Using these key pillars as a framework, evaluate offerings against your environment‘s scale, team setup, visibility needs and budgets.

Prioritize must-have aspects from nice-to-have augmentations based on the risk appetite around SSL disruptions. Getting the foundations right cost-effectively is crucial.

Once shortlisted, take chosen options for a spin. Validate proof-of-concept setups with freemium tiers or trials. Also factor any deprecation policies around legacy protocols or expiring root certificates.

Monitoring and Alerting Implementation

With scale comes complexity. Whether managing certificates across internal development, test and production environments or coordinating externally facing infrastructure, staying disciplined around monitoring is key.

Here are tips to smoothly operationalize visibility.

Staging and QA

Ensure staging sites with short-lived certificates get excluded from production inventory monitoring to avoid false positives. Test notification channels work early before relying critically.

Consolidate Credentials

Centralize certificates, keys and passphrases securely to enable automation instead of scattered individual handling. Rotate access before team changes.

Browser Feedback Loops

Feature flag a cohort to receive pings if warned of expiry or errors via extensions. Helps catch problems independently.

Protocols Supported

Beyond encryption, check what versions of TLS standards from 1.0 and later are validated by the tools for future-proofing as older ones get deprecated.

Wildcards and CDNs

Specify extent of subdomain and origin IP support needed when evaluating offerings if utilization is heavy.

Looming Regulations

Consider geo-specific regulations like Certificate Transparency enforcements and browser root program changes and impact.

automation Avenues

Leverage CLI integrations, API availability and built-in workflows around renewal triggering rather than entirely manual interventions.

With planning, what appears complex gets simplified to a great degree. Mature tools turn SSL monitoring into yet another observational metric your systems leverage rather than a source of frustration when not managed diligently.

Winding Up on Securing Trust

Hackers always target the weakest link and expired certificates are prime punching bags. With domain validated SSLs cheaper than ever, no excuse exists for exposure and risking customer data or privacy. Monitoring tools help companies and computing teams of all scales to uptrend security benchmarks.

On a closing note, don‘t overlook needing broader visibility into internet-facing risks. Beyond SSL expiry, factor monitoring phishing alerts, brand impersonation notices, data leaks detection and cyber threat intelligence keyed to domains.

Lots more ground we have only touched the tip of when it comes to fortifying website security and trust. But consistent rigorous tracking of SSL health marks a solid starting point to build upon. One less distraction so the focus stays on delighting customers.

Did you find this guide useful? Has it convinced you to finally tackle certificate monitoring? What other website protection areas would you like practical advice around? Look forward to your thoughts and feedback to cover in future writeups!