Slack Certificate Expiration Notifications Prompt
Detect and notify on TLS / SSH / code-signing certificate expirations in Slack — discovery, multi-window alerts, renewal automation hooks, owner routing, and post-renewal validation.
- Target user
- Platform / security engineers preventing the next 'certificate expired' SEV1
- Difficulty
- Intermediate
- Tools
- Claude, ChatGPT
The prompt
You are a senior platform engineer who has wired certificate-expiration alerts in Slack across thousands of certs (public TLS, internal CA, code-signing, SSH host keys) with zero outages from missed expirations. I will provide: - Certificate types in scope (public TLS via Let's Encrypt / DigiCert / AWS ACM / internal CA / SSH / code-signing) - Discovery methods you have (DNS scan, CT logs, AWS API, K8s cert-manager, manual list) - Ownership model (which team owns which cert) - Existing automation (cert-manager, certbot, Vault PKI, manual) - Pain points (expired cert outages, surprise renewals) Your job: 1. **Certificate discovery** — cover the surface area: - **Public TLS** — Certificate Transparency log search for your domains - **Internal TLS** — your internal CA's issued cert log + scan internal endpoints - **AWS ACM** — `aws acm list-certificates` per region per account - **Kubernetes cert-manager** — query CertificateRequests + Certificates - **SSH host keys** — ssh-keyscan + check for expiry where applicable - **Code signing** — registry of issued certs - **VPN certs** — vendor portal - **mTLS service mesh** — Istio/Linkerd's internal cert rotation 2. **Discovery cadence + inventory**: - Daily scan; store in inventory table - Diff against yesterday — alert on newly-found OR newly-missing certs - Manual entry for certs not auto-discoverable 3. **Multi-window alerts** — escalating urgency: - **90d before expiry** — info, weekly digest to team channel - **30d before** — warning to team channel - **14d before** — escalated, DM to cert owner - **7d before** — high severity, owner DM + service team channel - **3d before** — critical, page on-call - **1d before** — emergency, all hands - **Expired** — SEV1 + auto-create incident 4. **Owner routing**: - Each cert has an owner team + service in the inventory - Alerts go to: team channel + DM to current rotation owner - For ownerless certs (newly discovered): route to platform team for owner assignment 5. **Renewal automation hooks**: - For cert-manager-managed: auto-renew should be working; alert is a fallback - For ACM: auto-renewal for ACM-managed; only DNS-validated needed - For Let's Encrypt: certbot/cert-manager; alert if last renewal > 60d ago - For manual certs: provide renewal runbook link in the alert 6. **Bot integration for renewal**: - `/cert info <fqdn>` — show cert details: issuer, dates, owner, last validation - `/cert renew <fqdn>` — trigger renewal for auto-renewable certs (cert-manager / ACM) - `/cert validate <fqdn>` — fetch the live cert and verify dates match inventory - `/cert claim <fqdn>` — claim ownership (for unowned certs) 7. **Post-renewal validation**: - On renewal completion, bot verifies the new cert is serving live - Check expiry date moved forward - For load-balanced / multi-region: check all endpoints have the new cert - Post confirmation to team channel 8. **Anti-patterns to avoid**: - Single-channel firehose (every cert from every team) - Alerts to a generic ops channel (no one feels owner) - Inventory updated by humans (drift inevitable) - Missing certs (CT logs catch what you self-host doesn't) - No post-renewal verification (cert renewed in cert-manager but not deployed) 9. **Edge cases**: - Cert pinning (HPKP, mobile apps) — renewal still required; pinned hashes need update - Long-lived enterprise CA root certs — track separately, plan renewal cycles - Wildcard certs — single renewal covers many endpoints; mark in inventory - Backup certs / standby — track even if not currently active 10. **Compliance overlay**: - Audit log of every renewal - For regulated environments (PCI, FedRAMP): cert lifecycle is required evidence - Retention of expired certs for 1 year for audit - HSM-backed code-signing: extra-careful audit Output as: (a) discovery sources + cadence, (b) inventory schema, (c) multi-window alert policy, (d) owner routing rules, (e) renewal automation integration, (f) bot command catalog, (g) post-renewal validation, (h) edge case handling. Bias toward: discover broadly, route to a single accountable owner, multi-window escalation, validate after renewal, audit for compliance.