Founder & Developer · Aug 2026 - Present

Clickwill.

Clickwill edits the music library directly on an iPod classic: covers, titles, track order, CD import and duplicate cleanup. No sync folder, no custom firmware, and a backup before every write.

Visit clickwilldev.comSource on GitHub
Clickwill on an iMac, showing Cover Flow for the albums on a connected iPod classic
A silver iPod classic showing the same album in Cover Flow
Mac: Clickwill in demo mode with a real iPod connected. iPod: illustration based on iPod.js by Tanner Villarete (MIT License).

About 40,000 lines of Swift and SwiftUI

568 automated tests before anything touches a real iPod

6 public releases in six days

What it does.

Screen recordings of the real app.

Cover Flow, mirrored on the Mac.

Albums appear the way the iPod shows them, and every song plays straight from the iPod.

Try anything. Nothing is final.

Each backup says what the write changed and what a restore would bring back.

Artwork for every screen.

Change a cover once and Clickwill writes it in every size the iPod needs.

CDs without Apple Music.

Look Up Online fills in names, cover, year and genre from MusicBrainz, then Import CD saves every song.

Why I built it.

It started with my own iPod classic. Every sync with Apple Music added songs and samples I never asked for, and I could not change covers, track order or remove a single song the way I wanted.

So I wrote an app that opens the database on the iPod and changes only what I ask for, with no sync and no library on the Mac. Once it worked on my iPod, I released it for free, so anyone can put music on an iPod without iTunes or Apple Music.

What I used.

One person and a set of tools, each with one job.

Build

Swift and SwiftUI
The Mac app and its core library
Xcode
Builds, tests and signing
Claude Code
The AI agent that writes the code
Codex with Astra
A second AI model that audits it

Ship

Apple Developer ID
Signed by me, notarized by Apple
Sparkle
Updates inside the app
Cloudflare
Website, downloads and feedback on Workers, D1 and R2
GitHub
The open source code

Run

Proxmox homelab
Staging site and my own dashboard
Google Analytics
Site traffic, only with consent
Search Console
How people find the site
MusicBrainz
Album details when importing a CD

How I organised the AI agents.

I am the product owner and the tester. The engineering is split between AI agents, each with one job and clear limits.

What the agents do.

  • Main developer

    Writes the app, its modules and their tests, inside my rules. 568 tests and a full build run before anything goes further.

  • Code health

    Checks every new module from the main developer: tests it, verifies it works and holds the layers apart, so each layer and module does only its own job.

  • Website and SEO

    Builds clickwilldev.com and optimises it for search, with data from Google Search Console.

  • Cloudflare

    Organises and configures every domain I own, and the database Clickwill is downloaded from.

  • Security audit

    Astra in Codex, from another AI company, reviews changes to the write path, read-only.

What I do.

  • Decisions

    What to build, how it looks and which rules the code follows.

  • Testing

    Every change on a real iPod, by hand, to feel the friction.

  • Releases

    Only after my yes.

The rules the agents work by.

  • Nothing without my yes.

    Code, commits, builds and releases start only after I approve them.

  • Tested by hand, or it does not ship.

    Nothing goes further until I have tested it by hand and confirmed it works. Passing automated tests is not enough.

  • A memory that carries over.

    48 written notes on the device, my rules and past mistakes, read at the start of every session.

  • The iPod stays in my hands.

    Agents never write to my iPod. Every real write is mine.

From first byte to public release.

  1. 21 Aug 2026

    First read of my iPod.

    And the database signature matched on the first day.

  2. 21 Sep

    The first app window.

    Cover Flow loaded from the iPod, an album view and a list of pending changes.

  3. 3 Oct

    Public alpha.

    Version 0.1, signed, notarized and free to download from clickwilldev.com.

  4. 5 Oct

    Security audit.

    Astra found five issues in 0.1.3. The three most serious were fixed the same day, the rest three days later.

  5. 8-13 Oct

    Six releases in six days.

    Native macOS screens, choosing an iPod, a drawing of your iPod, Cover Flow and Albums.

  6. 18 Oct

    More Macs.

    Version 0.3.0 runs on macOS 14 Sonoma or later, not only macOS 26.

  7. 29 Oct

    Public beta.

    Version 0.4.0 edits the iPod nano 2nd generation, tested on the real thing.

  8. 30 Oct

    Open source.

    The code is public on GitHub under GPLv3.

After launch.

Releasing was the start. Since then I run Clickwill like a product.

200+ downloads in the first month

17 releases in the first month

40,000+ views of my posts on Reddit

  • Feedback from the app

    Send Feedback goes straight to my server, with no Mail and no e-mail address needed.

  • Updates on every launch

    Clickwill checks for a new version each time it opens and installs signed updates through Sparkle.

  • My own dashboard

    A panel in my homelab shows downloads, site traffic and search terms, refreshed through the day.

  • A public roadmap

    Every version, released or planned, is on the roadmap, and every release gets its own post.

Runs on
macOS 14 Sonoma or later, Apple silicon and Intel
Status
Free public beta
License
Open source, GPLv3
Built
After hours, on my own, with AI agents