This is a guest conversation episode of Ship It Weekly, separate from the weekly news recaps.

In this Ship It: Conversations episode, I talk with Evan Phoenix of Miren about why deployment is still painful, what teams keep getting wrong when they try to simplify it, and why small teams may need better defaults more than more platform knobs.

Evan is the CEO of Miren. He previously worked on Terraform Enterprise and Waypoint at HashiCorp, and he also built Puma and Rubinius.

We talk about deployment as the “final boss” of software delivery. Not because teams do not know how to ship code, but because deployment is where everything collides: runtimes, registries, secrets, networking, cloud services, databases, rollbacks, and the internal platform nobody wants to touch anymore.

A big theme is opinionated tooling. Engineers often say they want flexibility, but many teams are really asking for good defaults, a clear happy path, and fewer decisions to own.

We also get into Terraform Enterprise, Terraform Cloud, Terragrunt, OpenTofu, Waypoint, Kubernetes, Heroku, ECS, container registries, and how AI changes the deployment conversation. AI can generate infrastructure code, but when that setup breaks, someone still has to understand it and be on call for it.