Falling Down the Dotfiles + Devcontainer Rabbit Hole

September 30, 2025

I didn’t plan on spending my evening building a complete cross-platform dev environment — but here we are.

It started with a simple frustration: switching between macOS and Windows (via WSL) for development. Both work fine individually, but the little differences — path quirks, shell defaults, git configs, VS Code behaving slightly differently — were creating a steady drip of friction. Every switch meant more mental overhead.

First Attempts

My first thought was: “Can I just standardize around WSL on Windows?” That got me halfway there — a Linux environment on Windows smooths over some platform-specific rough edges. But I still had macOS in the mix, and I didn’t want to keep remembering what worked where.

I wanted one setup, one mental model.

That’s when the rabbit hole really opened.

The Solution: Dotfiles + Devcontainers

The answer turned out to be a combination of two tools:

Dotfiles repo → central home for .zshrc, .bashrc, .gitconfig, aliases, Starship prompt config, etc.
Devcontainers → reproducible development environments defined in devcontainer.json, fully supported by VS Code.

By combining these, I now have:

Consistent shells on both platforms (zsh on macOS, bash/zsh in WSL).
Shared git config & aliases so I don’t forget shortcuts.
Starship prompt for consistency and style (with optional Powerlevel10k if I want to go fancier).
Bootstrap script to set up Homebrew (macOS) or apt (WSL), Starship, NVM, Python, etc.
Setup script to symlink dotfiles in place.

And the cherry on top: a VS Code devcontainer that automatically applies the same environment (Python 3.11 + Node.js 20) with synced settings and recommended extensions.

Repo Structure

dotfiles-devcontainer/
├── .gitignore
├── LICENSE
├── README.md
├── FIRST_RUN.md
├── dotfiles/
│   ├── .aliases
│   ├── .zshrc
│   ├── .bashrc
│   ├── .gitconfig
│   ├── bootstrap.sh
│   ├── setup.sh
│   └── .config/starship.toml
├── .devcontainer/
│   └── devcontainer.json
└── .vscode/
    ├── settings.json
    └── extensions.json

First Run

To bootstrap a new machine:

./dotfiles/bootstrap.sh
./dotfiles/setup.sh

Then open the repo in VS Code — it applies the settings, suggests extensions, and asks if I want to reopen in the devcontainer. From there, I’m coding with the same environment everywhere.

Reflections

What started as “I just want fewer workarounds between macOS and Windows” turned into a polished setup:

Dotfiles that are clean, modular, and portable.
Devcontainers that lock in my stack.
A README + First Run guide so future-me doesn’t forget the steps.

This evening’s rabbit hole paid off. Next time I spin up a new machine, it won’t take me hours to remember how to configure things. It’ll be one git clone and a couple shell scripts.

And honestly? That feels like a win.