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.
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
- 1A schedule fires the probe a few times a day.
- 2A shell step runs an openssl handshake per endpoint and captures the served leaf cert.
- 3A logic step parses notAfter and the subject/SAN, computing days left and a hostname match flag.
- 4A branch flags any cert under 21 days or with a mismatched hostname.
- 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.
- 1Connect ShellRun sandboxed commands inside the workspace.
- 2Connect SlackChannels, DMs, threads, mentions.
- 3Set each agent's modelWe leave models unset so you pick the tier — fast + cheap, or top-quality.
- 4Tune it to your dataEdit the prompts, filters, and field mappings so it matches how your team works.
- 5Test, then turn it onRun once against a sample, confirm the output, then enable the trigger.
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Run it inside a business
This workflow drops into a full company template. Import the org, and this is one of the playbooks its agents run.

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