IT OPS

Live TLS Handshake Probe with Slack Expiry Alerts

Probes a list of public endpoints over the wire, reads the leaf certificate served during the TLS handshake, and alerts Slack when the live cert is expiring or mismatched.

CategoryIT Ops
Enginesim
Difficultyadvanced
Triggerschedule
Steps5
Setup~25 min

How it runs

The automated pipeline, trigger to output.

  • TriggerSchedule fires the live probe
  • ActionRun openssl handshake per endpointShell
  • LogicParse served cert expiry and hostname match
  • LogicFlag certs under 21 days or mismatched
  • OutputAlert failing endpoints to SlackSlack

What it does

Opens a real TLS connection to each endpoint you list and inspects the certificate the server actually presents, then checks its expiry and hostname match. This catches cases where the deployed cert differs from the issuer's records — a stale cert pinned on a load balancer, or a renewal that never got installed.

When to use it

Use it when your renewal pipeline issues certs correctly but you've been bitten by the new cert never reaching the edge. An inventory check trusts the registrar; this trusts only what the server serves right now.

How it works

  1. 1A schedule fires the probe a few times a day.
  2. 2A shell step runs an openssl handshake per endpoint and captures the served leaf cert.
  3. 3A logic step parses notAfter and the subject/SAN, computing days left and a hostname match flag.
  4. 4A branch flags any cert under 21 days or with a mismatched hostname.
  5. 5Slack receives a threaded alert listing the failing endpoints, served expiry, and mismatch reason.

Set it up

What you configure once, before turning it on.

  1. 1
    Connect ShellRun sandboxed commands inside the workspace.
  2. 2
    Connect SlackChannels, DMs, threads, mentions.
  3. 3
    Set each agent's modelWe leave models unset so you pick the tier — fast + cheap, or top-quality.
  4. 4
    Tune it to your dataEdit the prompts, filters, and field mappings so it matches how your team works.
  5. 5
    Test, then turn it onRun once against a sample, confirm the output, then enable the trigger.

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