Building Agent-Friendly CLIs - What we learned at Checkly

Building Agent-Friendly CLIs: Why Your AI Agent Already Loves the Checkly CLI

Stefan explains why products, docs, and CLIs must be AI-ready as coding agents rapidly become primary users of the Checkly CLI. He outlines key CLI features for agent workflows:

• built-in documentation
• progressive disclosure
• agent detection and guardrails
• structured output
• plan awareness

Stefan demos how an agent initializes project-tailored Checkly setup from scratch without any human intervention and also shows how agents can entirely automate the incident life cylce from resolution to status page communication.

00:00 Welcome and agenda

00:40 Meet Stefan and Checkly

02:18 Why agents need CLIs

03:52 Monitoring as code basics

05:57 New CLI features shipped

06:51 Demo project overview

08:54 CLI skills and docs

11:23 State and incidents via CLI

14:47 Agent friendly init flow

15:24 Skill files and detection

19:21 Claude sets up monitors

22:06 Generated Playwright check

22:57 Accepting Generated Checks

24:23 Testing and Fixing Redirects

27:17 Reviewing Check Config

28:05 Reverting Setup for Demo

29:56 Breaking Login on Purpose

31:45 Investigating Failed Playwright Run

32:34 Captcha Monitoring Q&A

33:41 Agent Triage and Root Cause

35:17 Opening Incident with Guardrails

37:04 Deploying Fix and Verifying

41:08 Why CLI Skills Matter

43:10 Wrap Up and Next Steps

#checkly #monitoring