The stack · updated

Every tool
replaced one.

What I use, what I used before, and why I moved each time. A new tool usually won because the way I worked had changed, not because the old one got worse.

  1. 01 Terminal Terminal.app → iTerm2 → Warp → iTerm2, again → cmux → Orca · trying herdr
  2. 02 Operating system Windows → Ubuntu → Windows + WSL → macOS · trying Omarchy
01 / Terminal

Six stops,
five terminals.

Counting from when I moved to the Mac. Each switch happened because the way I worked changed and the terminal I had stopped fitting it, most of all once I was running a dozen agents at a time.

  1. Terminal.app Dec 2022, briefly
  2. iTerm2 Dec 2022 – Jul 2024
  3. Warp Jul 2024 – Oct 2025
  4. iTerm2, again Nov 2025 – Jul 2026
  5. cmux Jul 2026 – Oct 2026
  6. Orca Oct 2026 – now
  7. herdr trying · lightweight alt
01

Terminal.app

Dec 2022, briefly

The one that ships with macOS.

In
It was already there, like it is for everyone on their first day with a Mac.
Out
No split panes, weak search, and no true color until 2025. It lasted two days.
02

iTerm2

Dec 2022 – Jul 2024

The long-time power-user terminal for macOS.

In
The standard upgrade: split panes, a hotkey window, search across scrollback, profiles, full color. It arrived the same week I started my own zsh plugin.
Out
Warp was the terminal everyone was talking about, and it was built around AI. I wanted to know what that felt like day to day.
03

Warp

Jul 2024 – Oct 2025

A terminal that also takes over parts of the shell: its own input editor and its own completions replace zsh’s.

In
AI built into the terminal, and an input box that edits like a text editor instead of a command line.
Out
That take-over was the problem. In September 2025 I built my own command-line tool with its own tab completion, and Warp’s completions kept winning over mine. I needed a terminal that runs the shell and stays out of its way.
04

iTerm2, again

Nov 2025 – Jul 2026

Back to a plain terminal emulator.

In
zsh handles typing and completion again, so everything I had built for it worked.
Out
Then the number of agents went up. I scripted a grid of fifteen Claude Code sessions, lost sessions when a window closed by accident, and could not tell which pane needed me.
“I want a grid that is 5 x 5 (25 sessions).”Prompt to Claude Code, Jan 14, 2026
05

cmux

Jul 2026 – Oct 2026

A native macOS terminal built on Ghostty, made for running many coding agents at once.

In
It is built for exactly that: a sidebar of workspaces, a ring when an agent is waiting on me, a browser inside the terminal, and a command line that agents can use to drive the terminal themselves.
Out
It only runs on the Mac, and its phone app was slow. I had started handing work to a Linux server and wanted the same setup everywhere.
“The difference with cmux versus any other terminal: you could control it agentically. That opens up all kinds of possibilities.”On a call, Jul 29, 2026
06 now

Orca

Oct 2026 – now

An “agent development environment”: each task gets its own agent in its own copy of the code.

Phone appUI / UXRemote sessionsMac, Linux, Windows
In
The killer feature is the phone app: I check on and steer every agent from my phone, and it is really good. The interface is the most polished of any terminal I have used, and sessions can run on a remote machine as easily as on my laptop.
Gaps
It is not as geared to power users as I would like, so I have sent it six pull requests so far.
“Orca has pros and cons. For most people it would purely be pros.”On a call, Oct 11, 2026
↳ trying

herdr

Oct 2026

An agent multiplexer: one small program that runs inside whatever terminal you already have and tracks what each agent is doing.

In
Not a replacement. I am customizing it to see if it can be an occasional lightweight alternative to Orca, for a quick session on a bare server or a machine where a full app is too much.
Not yet
Out of the box it needs a lot of setup, and it does not have Orca’s phone app, interface or small conveniences. Orca is winning, clearly.
Orca herdr
Phone app Really good None
Interface Polished app Text in a terminal
Remote sessions Built in Run it over SSH
Setup Works on day one Lots of customizing
Weight Full desktop app One small binary
Orca 4 – 1 herdr
02 / Operating system

Four operating systems,
and one on the side.

The longer arc, back to my first websites in 1998. Roughly dated: most of it happened before I kept records.

  1. Windows From 1998
  2. Ubuntu In between
  3. Windows + WSL Before the Mac
  4. macOS Dec 2022 – now
  5. Omarchy trying
01

Windows

From 1998
In
The computer I grew up on. My first websites were built on it, with ASP, Access and FrontPage.
Out
Windows is the least terminal-based of them all, and the servers I was building for ran Linux.
02

Ubuntu

In between

Linux on the desktop.

In
The terminal comes first, and it is the same kind of system the servers run.
Out
Hardware support and everyday apps were a constant fight.
03

Windows + WSL

Before the Mac

Windows with a Linux system running inside it.

In
A way to keep Windows’ hardware support and apps and still have a real Linux shell.
Out
Two systems glued together, with Windows still underneath.
“Windows is not really for the power users.”On a call, Apr 29, 2026
04 now

macOS

Dec 2022 – now

A MacBook Pro, M1 Max, maxed out when I bought it and still my main machine almost four years later.

Terminal-firstHardware that just worksRaycastNative apps in minutes
In
I spent my whole life on Windows or Ubuntu before this. The Mac is the first one that is good at both halves: a real Unix terminal underneath, on hardware and apps that just work. Now that AI work happens in the terminal, that combination matters more every year.
Gaps
Price, and one laptop runs out of room when two dozen agents are running. The next step is probably a Mac Studio.
Why it works for me
  • Best of both worlds Windows has the hardware support but not the terminal. Linux has the terminal but not the polish. The Mac has both.
  • The client, not the server I work from the MacBook and send heavy jobs to Linux machines, which cost a third of what the same power would on a Mac. Mac for the client, Linux for the servers.
  • Raycast Anything on the computer is a few keystrokes away. More on it below.
  • Native apps in minutes With Swift and an agent, a small menu-bar app for my own workflow takes about ten minutes to build.
  • Muscle memory Three years in, going back to a PC is hard. That is the real test of a switch.
“macOS as a client is by far the most productive machine.”On a call, Jul 22, 2026
↳ trying

Omarchy

Sep 2026

An opinionated Arch Linux setup with the Hyprland window manager.

In
It runs on my old ThinkPad X1 Extreme, which is now a backup machine and a second screen. Everything in it is configured from text files, so agents can customize it. I am working out which apps to write for it.
“A Linux distribution that’s very popular right now, and it’s very AI friendly.”On a call, Oct 11, 2026

Last updated . More categories are coming: editor, launcher, browser. Dates come from install records, my prompt logs and recorded calls where those exist; older eras are from memory and approximate.

· made with AI (Lyria)click to resume