Operations | Monitoring | ITSM | DevOps | Cloud

The post-mortem problem

Post-mortems are one of the most consistently underperforming rituals in software engineering. Most teams do them. Most teams know theirs aren't working. And most teams reach for the same diagnosis: the templates are too long, nobody has time, and nobody reads them anyway. These aren't wrong observations. But they're symptoms, not causes. The actual problem is that somewhere along the way, the post-mortem stopped being a piece of communication and became a compliance artifact.

We Turned Our WireShark Wizard Into a Markdown File

Rocky AI — Checkly’s AI agent — is now Generally Available. We developed Rocky AI over the last ~6 to 8 months. This is an aeon in AI-years. During this period, we learned a ton. About AI, but mostly about how to fit them into an existing SaaS product, not just another chat widget. This is my ramble…

Introducing Rocky AI to General Availability

After months of being available in Beta for our app users, Rocky AI is now generally available to all users and plans. Rocky AI is Checkly’s AI agent that works around the clock, 24/7, to make sure your application’s reliability is optimal. In this first release, Rocky AI ships with the ability to run continual Analysis on test and check failures, giving your teams AI-powered root cause analysis, impact analysis, and more.

Beyond "Reactive" Accessibility: Meeting the 2026 ADA Title II Mandate in Higher Ed

For decades, digital accessibility in state-funded higher education has largely been a "reactive" game. If a student with a visual impairment reported an issue with a tuition portal, the university would scramble to provide an accommodation. As long as the institution could show "meaningful progress" toward compliance, it was generally shielded from significant legal repercussions. That era is officially ending. The U.S.

Buy vs Build in the Age of AI (Part 1)

A few months ago, I spoke to an engineering manager who proudly told me they had rebuilt their monitoring stack over a long weekend. They’d used AI to scaffold synthetic checks. They’d generated alert logic with dynamic thresholds. They’d then wired everything into Slack and PagerDuty, and built a clean internal dashboard. “It used to take us weeks to prototype something like this,” they said. “Now it’s basically instant.” They weren’t wrong.

Why Planning Your Estate Early Can Protect Your Family's Future

Many people think estate planning is something to handle later in life. But waiting can leave your family unprepared and stressed during difficult times. Creating your estate plan early helps you decide how your assets will be managed, who will care for your loved ones, and how your wishes will be followed. It also helps avoid legal delays, family conflicts, and unnecessary costs.

Claude Code Security Launch Triggers Cybersecurity Industry Reassessment

On February 20, 2026, Anthropic launched Claude Code Security, an AI-based tool to scan codebases, identify security weaknesses, and provide patching solutions. The Claude Code preview caused a panic that resulted in billions in lost market capitalization among cybersecurity stocks. CrowdStrike shares decreased by 8%, reaching approximately $388.87, while Okta experienced a 9.2% decline and Zscaler saw a 5.5% drop in its stock price. That demonstrates the increasing investor anxiety about AI technology developments that threaten to disrupt established cybersecurity frameworks.