Jeffrey Bergier

ENIL: LINE Messenger for Retro Devices

2026-06-22T00:00:00+00:00

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What is ENIL

ENIL is my custom-built LINE companion client for retro Apple devices. It brings the core messaging experience to systems that the official LINE apps no longer support. The Mac app targets Mac OS X 10.4 Tiger and later, with PowerPC, 32-bit Intel, 64-bit Intel, and Apple silicon slices in one universal binary. The iOS app targets iOS 4.3 and later and includes armv7 and arm64 slices.

Not having a working LINE application was a real hurdle to using my iPhone 5 running iOS 6 as my primary iPhone. While the old LINE app still exists for iOS 6, it no longer does anything, not even present an error. I live in Japan, where LINE Messenger is a huge part of daily life. And it was not only my iPhone: I also have a 12-inch Retina MacBook Adorable that I use every day. This computer runs Mojave because it is extremely fast, but the official LINE Mac application no longer works there either. The official clients no longer support either system, which left a significant gap in my daily setup.

So I built ENIL so I can use LINE to stay in touch with my friends on my Retro Devices that LINE no longer supports. I have been using it daily for a few months now and I am extremely happy with how it has turned out.

What is LINE Messenger

If you have lived in Japan, Taiwan, or Thailand, then you probably know LINE Messenger. It is a standard way for people, restaurants, and other businesses to communicate. It works similarly to WhatsApp or iMessage, and contacts can be added via QR code. It has the usual features of a modern messaging app, including groups, voice calls, and video calls. Most importantly for this project, it uses Letter Sealing, LINE’s branding for end-to-end encryption. Supporting Letter Sealing was therefore essential for ENIL.

ENIL Features

QR code login
History sync
Purchased Sticker and Emoji sync
One-to-one and group chats
Sending and receiving stickers, emoji, and photos
Separate ‘Seen’ and ‘Read’ states
A Mark as Seen button, rather than automatically marking a chat when I open it
Multiple accounts

Caveats

ENIL depends on a Cloudflare Worker for cryptographic operations.
It does not include every LINE feature. Major omissions include voice and video calling and interactive features used by LINE Official Accounts.
ENIL is an independent personal project and is not affiliated with, endorsed by, or supported by LINE. Because it depends on an online service that changes over time, future LINE updates may require corresponding ENIL updates.
This is a niche app, mainly useful to LINE users who also enjoy retro devices.
ENIL is a companion client, not a replacement for LINE’s main mobile app. You still need a working modern LINE device to scan and approve the login QR code and to manage the account.
I do not have an iPhone running iOS 4.3. ENIL should work on iOS 4.3, but I have not tested it.

How Can You Get It

ENIL is still a personal project, so its repositories remain private for now, but I hope to share more in the future. In the meantime, if you are interested in testing ENIL, please contact me on Mastodon:

@jeff@jeffburg.social

How Does ENIL Work

After you log in by scanning a QR code with LINE’s main mobile app, ENIL syncs the available history, purchased stickers, and emoji. Each account keeps its own session state and SQLite database. ENIL then opens a Server-Sent Events (SSE) connection through which LINE delivers new messages, read state, and other metadata. The client records the last operation revision so it can reconnect from that point after a timeout or sleep; if LINE requests a full sync, ENIL performs one again.

Account metadata, chat state, original message data, and downloaded asset paths are stored in SQLite. When you open a chat, ENIL generates an HTML page in C and loads it into a WebView. These WebViews do no networking because retro devices have old TLS stacks that do not support TLS 1.1/1.2. Instead ENIL links a custom build of libcurl provided by Altivec Intelligence. The C code in ENIL does all the networking, JSON parsing, and database storage directly before handing anything off to Objective-C for showing in the UI. Avatars, stickers, emoji, and other assets are first downloaded to disk and then the Webviews render them from there.

When an SSE event arrives, ENIL writes it to the database and posts a notification through NSNotificationCenter. An open view controller can then append the new message to its WebView with JavaScript. On systems that support local notifications, ENIL posts one for a new message only while the app is in the background. On iOS, ENIL declares the VoIP background mode and embeds the private unlimited-assertions entitlement, so it can remain connected to LINE’s SSE stream while running in the background.

Encryption and Letter Sealing

Messages protected by Letter Sealing arrive encrypted, whether fetched during sync or received over SSE. Before displaying the message, ENIL sends the ciphertext to the Cloudflare Worker and receives the decrypted content. When sending a message, the Worker performs the reverse operation and ENIL sends the resulting ciphertext directly to LINE. The need for the Cloudflare worker is described later but I think it is unavoidable on retro devices for now. That said, Cloudflare workers have no state and no storage, or at least I do not use those features for this worker, so I think we can consider this to be secure. But use at your own risk.

UI Structure

The iOS and Mac apps share the same basic structure. The chat and friends lists are native table views. This was a bit tricky because Mac OS X did not get view-based table views until 10.7, and I support 10.4. On Tiger, ENIL therefore uses a custom NSCell which draws its contents manually with AppKit. This is inconvenient, but it works.

Each individual chat is a WebView. When you receive a new message, JavaScript appends it to the open WebView. Sticker and emoji pickers are also WebViews. Some of the stickers and emojis use animated PNG files. If you are running iOS 8 or OS X 10.10 Yosemite or later, then the WebView will animate these automatically. On earlier systems they appear as static images.

One main Mac and iOS feature difference is that Mac OS X has supported NSAttributedString and NSTextAttachment since before Mac OS X even existed. Yes, even OpenStep 4.2 had these features. AND YET, iOS lacked them until around iOS 7. On the Mac, a custom emoji therefore appears inline in the message text as you type. On iOS, I use a simple Unicode placeholder; the custom emoji appears only after you send the message, when the WebView can properly render the text and images inline on any platform.

The Game

LINE has the concept of a “companion app.” I have used the Mac version of this for a long time. For a while I was thinking I would not even need to talk directly to LINE because I could just read the data out of the Mac app’s database. But it turned out there was also a Chrome extension companion app.

I was super excited when I learned this because browser extensions are just a bunch of JavaScript. So yes, it will be minified and obfuscated, but all the code is there! No need to decompile or sniff the network traffic. All of the code is just sitting there!

WebAssembly: The Final Boss

So I downloaded the Chrome extension and asked the AI to format the minified JavaScript and find the app’s key functionality. When its summary came back, my heart sank a bit. These LINE companion apps rely on a large 3 MB WebAssembly (Wasm) binary blob to do much of their work. When I first heard of WebAssembly, I was excited that people could ship performant compiled code to the browser. What I had not considered was that now vendors could ship “closed source” code to the browser. In other words, it is no longer just JavaScript that can be easily read and evaluated.

At this point, I thought my journey was dead. There was no practical way to make these retro systems run WebAssembly code. My iMac G4 shipped in 2003 and my iPhone 5 in 2012, years before WebAssembly even existed. Getting the binary to run on these devices would easily exceed any amount of time I could commit to this project, with or without AI.

Cloudflare: It’s Highly Effective

At some point, in the shower probably, I realized “Wait! I don’t need to run WebAssembly on the device! I only need to run it in Cloudflare!” The Wasm blob only did basic cryptographic operations, which meant I could put a simple JSON interface in front of it and just use normal HTTPS requests to interact with it.

So I asked the AI to make me a simple Cloudflare Worker that “booted up” the Wasm blob and exposed its critical functions. The worker and the Wasm binary handle a lot of misc cryptographic functionality such as HMAC operations, key generation, keychain unwrapping, and group-key operations. This enables ENIL to interact with LINE’s very secure API with full Letter Sealing (E2E Encryption) functionality maintained.

From there, I had the AI cook up a little CLI-based JavaScript app that used the LINE API as presented by the Chrome extension and the Cloudflare Worker to successfully:

Log in to the “Chrome extension” by scanning a QR code with the LINE app on my phone
Download a list of recent chats
View a message conversation
Send a message

This PoC was extremely important because it proved that I could implement a compatible companion client and interact with the LINE API directly. My client still needed the Cloudflare Worker for cryptographic operations, but it made every LINE request itself. From LINE’s perspective, the requests were coming from a client device running Chrome from a normal client IP address.

Cocoa Level-Up

So a stupid little JavaScript PoC was fine and all, but it was time to 1-Up this bitch and get a real Mac and iPhone app working… for Mac OS X Tiger and iOS 4.3 . No but really, but this kind of app is conceptually simple and should not require any modern APIs. Chat apps have existed for Mac OS X and iOS for as long as both platforms have existed. The only thing I would need is modern networking which is thankfully provided by my bedrock development environment Altivec Intelligence. This includes all the basics like modern OpenSSH, libcurl, and cJSON for modern networking. It also provides a modern build of SQLite. With this basic bedrock I can build apps that interact with Modern Web APIs, save the info to the database and display it in the UI.

AI Power-Up

When I was originally thinking about Altivec Intelligence and how I would write code for retro devices, I thought, “No big deal. I need to use libcurl, cJSON, and SQLite, but I can wrap them in little Objective-C wrappers and then do normal Cocoa programming.” However, after I thought longer about it, I realized that these wrappers provided by Apple are actually quite huge and complex. They are nice but would I really want to rebuild them myself? Also, since old Apple platforms do not have NSJSONSerialization, it means I need a C-based JSON parser. So that means that libcurl is in C, cJSON is in C, and SQLite is in C… so I just couldn’t help but think “Why would I bridge back and forth between C and Objective-C if all of these libraries are in C anyway?”

So I asked this question to the AI and it said it had no issues writing everything in C… so that’s what we did. And it worked… like super well. AI plus the combo of LLVM/GCC -wAll and LLVM static analysis meant that there was plenty to reason about in terms of the stability and correctness of the code. In fact, it’s extremely stable and EXTREMELY fast. Yes it’s also insanely verbose… but that’s ok, it’s being generated by a computer.

Basically, I came to the realization that just because my comfort zone is Objective-C and Swift, it does not mean I need to do every task in those languages. Instead, I could accept the AI’s help and start writing code outside my comfort zone. I decided to use AI to help me write the C engine while keeping the UI in Objective-C. I ended up with a shared iOS and Mac codebase that is about 75% C and 25% Objective-C.

I will post more about this so stay tuned. But this is one of the great powers of AI-assisted programming. Instead of trying to do everything in the language you personally prefer, use the right language at the right time for the right job. AI makes that jump less intimidating, but generated code still requires planning, validation, and testing on real devices. Also, producing and validating thousands of lines of C also took far more tokens than producing something similar in JavaScript. At this point, I had to move from my $20 plan to the $100 plan to support this use case without constantly hitting limits.

ENIL is Right for Me

ENIL is my own personal app. It’s made by me, for me, and I use it every day and I love it. It means I can use the devices I want to use when I want to use them and still stay in touch with my friends. It ~~proves~~ shows that you don’t need an Apple silicon powerhouse chip with gobs of RAM and a 300 MB binary to do simple things like chat apps do. It’s simple, it’s fast, and it works, for me.

Unenshittification Manifesto

2026-05-22T00:00:00+00:00

What I have learned

This manifesto grew out of about five months of “spare time” spent trying to unenshittify my life. I now have everyday apps running on ancient computers like my iPhone 5 and iMac G4. That success has convinced me that, without enshittification, everyday apps could offer better user experiences and run on nearly any computer built since 2010.

What is an everyday app? A basic native application that fetches user data from a web API, stores it locally, displays it in a UI, and lets the user change and synchronize it. That describes every chat app, every doomscrolling social media app, every “AI” app, and pretty much any other app except games and apps for producing audio or video. I am pretty confident these apps account for 99% of the time you spend on your phone.

What I refuse

I refuse to accept that everyday apps require modern hardware
I refuse to accept that everyday apps require 300 MB of human-made slop
I refuse to accept being denied access to my own data
I refuse to accept digital experiences that are actively hostile to my goals
I refuse to carry a 7-inch supercomputer merely to chat and doomscroll

What I believe

I believe that users should decide what code runs on their computers
I believe that everyday apps can run GREAT on retro hardware
I believe that a GREAT everyday app can fit in a 5 MB binary
I believe that my data is my data and I can use it where and how I want
I believe that GREAT experiences help me achieve my goals
I believe that I can create my own GREAT experiences

What I accept

I accept that I cannot fix the modern app and web ecosystems
I accept that I cannot force Apple to give users control of their own data
I accept that the apps I create are not 100% feature-complete
I accept that the apps I create are not 100% bug-free
I accept that AI slop is neither beautiful nor pleasant for humans to read
I accept that AI slop is not free

What I will do

I will build my own apps for my own devices
I will make my data accessible to my own apps
I will use the devices I want to use
I will make AI slop apps outperform human slop apps in speed, stability, and focus
I will use AI to write MOST of my code
I will compile ALL of my code

I Will Unenshittify My Life

Altivec Intelligence

2026-04-22T00:00:00+00:00

Lessons Learned

In 2024 I developed MathEdit for OpenStep. This app was a proof of concept to see if I could develop a Cocoa application for OpenStep and then upgrade it to work on every version of Mac OS X. The application was a success, but even though it was a simple app, it took me exactly one year of spare-time programming to develop and then to upgrade through 20 years of Mac OS X history. The primary reasons for this were that Objective-C from 1996 was pretty painful to write, and I was writing it all in real OpenStep and vintage Mac OS X virtual machines with ancient tooling.

In the age of AI, this solution was not going to suit me anymore. I needed a modern environment that could run on any computer and still create apps for my favorite retro platforms. I needed this platform to support AI because it reduces the pain of writing Objective-C 1.0 code that lacks:

Automatic Reference Counting
Fucking Block Syntax
Property Syntax
Dot Syntax
Grand Central Dispatch
Collection Literals

Altivec Intelligence

Altivec Intelligence is an all-in-one integrated development Docker container that has everything I need to develop Cocoa and Cocoa Touch applications that run on PowerPC Macs with Mac OS X Tiger or later and iPhones running iOS 4.3 and later. And before you ask, yes, the Mac apps are universal binaries with four slices: PowerPC, x86, x64, and arm64 .

On top of that, Altivec Intelligence includes tooling for web development, image manipulation, and FFmpeg. Most importantly, all of the AI agent CLIs are baked into the container.

Why is this important? Well, these agents are incredibly powerful and help me to unenshittify my life. But they cannot be sandboxed and cannot be trusted as long as they have Bash access. By running them in a Docker container, I can safely run them in YOLO mode with no risk to my own Mac. They have all the tools they need to create great apps, all without ever changing my development environment or editing files outside of my repositories.

Libraries

A modern retro toolchain wouldn’t be complete without modern libraries to help these retro systems do modern tasks. Altivec Intelligence includes critical libraries bundled into dynamic frameworks and static libraries.

AltivecCocoa: Includes Font Awesome and other helper classes that make it easy to build applications that run across 20+ years of Apple history
AltivecCore: Includes modern networking and database tooling to interact with modern web APIs
- SQLite 3.43.2
- libcurl 7.88.1
- OpenSSL 1.1.1w
- zlib 1.2.13
- cJSON 1.7.19

Tooling

I will not go into all the details because you can view them on GitHub. But Altivec Intelligence includes a lot of basic tooling to make it easy to build, deploy, and debug apps to retro devices. This all relies on SSH key authentication, which can also be customized because the container mounts the home folder in ~/.altivec. This way you can always control which keys the container (and the agents) have access to. altivec-deploy is an included script that can deploy your apps to Macs and to jailbroken iPhones to start debugging sessions with GDB or LLDB. altivec-release automatically bumps the versions of the apps in the Info.plist files.

Caveats

Altivec Intelligence is offered as a prebuilt Docker container for arm64 and x64 devices. It supports arm64 and x86-64 computers capable of running Docker.

It does not include Apple-proprietary tooling, so there is no support for NIBs, for example. Deploying to an iPhone requires a jailbroken iPhone with SSH installed. Supporting Mac OS X Tiger requires using a lowest common denominator of Mac OS X APIs. The AI will help you do the runtime introspection, but it can be a pain.

For usage instructions and example apps, see the project on GitHub.

https://github.com/jeffreybergier/AltivecIntelligence

RSS-THE-PLANET

2026-03-22T00:00:00+00:00

The Primary Feature: Doomscrolling

The dark secret of the vast majority of mobile apps we use, on iOS and Android, is that they are basically doomscrolling apps. Now that does not mean that they are serving you malicious content necessarily. But they all have the same basic UX and use the same basic implementation details. Whether the app is:

These apps all use the same basic technologies and features which are all really simple in principle.

Fetch a list of content via JSON
Save or cache that data in an SQLite database
Convert that JSON into a model that is useful for the view (ViewModel)
Display the list of ViewModels as a list in the UI (UITableView)
Asynchronously download related assets such as images and video

It is important to point out that all of these capabilities have been built into iOS since iOS 5. This is super simple and obvious behavior that all mobile apps share.

Really Simple Syndication

You may not know this, but there is a really old technology that enables all of this functionality that is used by almost every website AND almost every podcast on the internet called RSS. RSS uses XML instead of JSON, but it enables the same basic functionality using a category of apps called RSS readers. Common examples are:

RSS-THE-PLANET

RSS-THE-PLANET is a very simple Cloudflare Worker application that can encrypt and store your credentials for your doomscrolling apps and then fetch their JSON APIs and convert them into normal RSS. Combine this with an RSS reader and now you can enjoy your favorite doomscrolling content on a retro device. For me, that retro device is an iPhone 5 running Reeder on iOS 6.

In fact, this improves the experience because these RSS reader apps often support offline viewing. So yeah, now I have easy access to all of my doomscrolling content even when totally offline:

RSS-THE-PLANET also includes basic features to proxy websites and images through Cloudflare to downgrade their TLS restrictions to 1.0 or none at all for older devices that do not support TLS 1.2 natively.

Caveats

RSS-THE-PLANET is not a hosted service. But the code is MIT licensed and so you can run it yourself for free in your Cloudflare account.

https://github.com/jeffreybergier/RSS-THE-PLANET

Note that this approach is inherently insecure. While your credentials are encrypted in Cloudflare, the generated RSS URLs allow unauthenticated access to your feeds. So please use with caution and keep your RSS feed links secret.

2026: The Year of Unenshittification

2026-02-22T00:00:00+00:00

Enshittification

In 2026, I set a goal to unenshittify my digital life. I am old enough at this point that I came of age when the internet was new and exciting and was built with good intentions. But for the past 10 years or so, it really has all changed for the worse. I won’t list all of my grievances, but I think I can easily argue that the web is mostly dead, apps have turned into cesspools of addictive nonsense, Mac apps are all now Electron apps, and the reality is that what we have done with all of the amazing power of our modern computing devices is waste it all on heavyweight frameworks, RAM-sucking JavaScript apps, and totally unwanted features. I am done with this computing contract. This is not what I signed up for.

I am starting to sound like an old man, and that is OK because at least I still have my Mac. Despite Apple’s best attempts, they have not been able to suffocate the Mac like they have all of their other platforms. On my Mac, I am in full control of my data, full control of the apps I use, and in full control of the services my Mac runs. The iPhone, on the other hand, has turned into a platform I absolutely despise. The App Store restrictions have turned one of the most exciting and powerful computing platforms into an addictive doomscrolling appliance with little other purpose.

Complaints

The thing is that every app for the iPhone has never actually really changed. Whether it’s 2012 or 2026, every app is fundamentally the same:

Download JSON
Store JSON in a SQLite database
Parse JSON into a list
Fetch media while the list scrolls
If I am being generous, on some chat apps there is some cryptography

All of these capabilities are provided by Apple and built into the OS. So all of these apps should be simple, small, and efficient. Yet they are not. You can pick your favorite doomscrolling app from the App Store and they are all 300 MB+. Why is this? Well, it is different for every app. But usually it comes down to:

Tracking frameworks
Advertising frameworks
Cross-platform UI frameworks
Unwanted features
etc., etc., etc.

This combined with the fact that Apple keeps making the iPhone bigger, more powerful, and more power-hungry, leaves me in such an awkward position. Since the apps are nigh useless for anything except doomscrolling, please tell me again why I need an 8” supercomputer with 12 GB of RAM in my pocket? All of this stuff could be done with an iPhone 5 in 2012 if it wasn’t all enshittified.

Reaction

That’s what I am doing. I am switching to using an iPhone 5 as my main iPhone. Why the iPhone 5? Well, it’s the newest iPhone that can run iOS 6 and it has a widescreen and a Lightning connector, unlike the iPhone 4s. So I could do a 5s or an SE and get the same size, but I thought it would be fun to have that retro design for the OS as well. Of course, I also have my lovely iMac G4 which would also benefit from the enhancements I made to the iPhone 5. This would later turn out to be a bigger challenge than I thought, but I will save that for later.

But long story short, my iPhone 5 is my day-to-day iPhone. I did also downgrade my gigantic iPhone 14 Pro to an iPhone 13 mini which serves as my backup iPhone when I need to do things the iPhone 5 can’t… like make calls, enable my Apple Watch (with Apple Pay), and use the enshittified apps that I have no choice but to use.

AI Slop

I will just say it up front. It is not possible for a single person working in their spare time to recreate their digital life without AI. I will be posting a lot about AI because it has honestly changed my life when it comes to programming. But for the doubters out there, I have 2 primary arguments.

All of our favorite apps and services were all fully enshittified well before AI was a thing. These apps became bloated 300 MB behemoths well before AI. AI is not going to ruin software; it was already ruined. The software we have to use daily is 100% human-made slop.
So much code we write basically does data conversions and data storage and retrieval; basically, taking JSON and storing it in a database or reading from a database and converting data to JSON. This kind of code is not interesting, not fun to write, and we should not waste human time to write this kind of boilerplate code (or crazy abstractions that attempt to make this task tolerable).

But AI will help me fix that, and for that reason, I love it.

Invitation

Follow along with me while I unenshittify my life. At the very least you can have a good laugh at how much personal time I am ~~wasting~~ spending to recreate experiences that are already free. But don’t doubt too hard. For one, they are my experiences created only for me. And two, I think you will be actually shocked at what is possible on these retro devices in 2026 when you have the right build environments, toolchains, and a little creativity.

How to Sync iPhone 5 with PowerPC Macs

2026-02-16T00:00:00+00:00

iMac G4 and iPhone 5	iTunes Screenshots

Table of Contents
Overview
TL;DR
- Tutorial
- Caveats
Background
- But Why
Approach

Overview

In this article, I will briefly show you how to get an iPhone 5 to sync with any Mac running Mac OS X 10.5.8, and yes, this includes PowerPC Macs. Syncing the iPhone 5 with PowerPC Macs was never possible because Apple restricted the iPhone 5 to Mac OS X 10.6.8 or higher.

TL;DR

When the iPhone and iTunes communicate with each other, they do a handshake involving a lot of property list (PLIST) XML passing. iTunes will start key exchanges and then the iPhone will send a large PLIST payload that explains the capabilities of the device such as the supported languages/regions, sync features, and, most importantly, the minimum version of iTunes required by this iPhone. This part of the PLIST is stored in the key “MinITunesVersion.” iTunes then checks this key and if the value is larger than the current version, iTunes will display an error saying which version of iTunes is required. Most importantly, this key is not present when the iPhone 4s and iTunes do their handshake.

So to bypass this check, all we need to do is change the “MinITunesVersion” string hard-coded into the iTunes binary to anything else and iTunes will then check for a key that does not exist in the PLIST XML provided by the iPhone and then iTunes will happily not display an error and bring you straight to the normal syncing screen in iTunes.

Tutorial

Download your favorite binary hex editor for your PowerPC Mac, such as Hex Fiend (Macintosh Repository, Macintosh Garden)
In Finder, click Go→Go to Folder and type in /Applications/iTunes.app/Contents/MacOS
Back up the iTunes binary by right-clicking on it and choosing “Compress”
Open the iTunes binary in the hex editor
Search for the string “MinITunesVersion” (there should only be 1)
Change it to literally anything else
1. I changed mine to “MinITuMesVersion”
Save the changes
Relaunch iTunes; you’re good to go

With this approach, I have been able to sync Apps, Music, Podcasts, iPhoto, and Videos. Even the feature that allows you to rearrange your home screen from iTunes works fine.

Caveats

This is a hack and may not work properly: hacker beware
After performing this hack, iTunes forcefully exits when trying to play any video. VLC has way better video playback performance so this is not a problem for me.
- I assume there is some sort of checksum iTunes checks before it tries to play video to protect DRM-protected content, but I have not tried to troubleshoot this yet.
This might work for iPhone 5s and others but I have not tried
This may not work on newer versions of iOS. I was using iOS 6.1.3 but if your iPhone 5 is running a newer version, this may not work.
- I confirmed this does not work if the iPhone is running iOS 10. I have not yet tested on iOS 8.

Background

You may or may not remember, but when the iPhone 5 was released, its official minimum system requirement was Mac OS X 10.6.8 Snow Leopard or newer. This of course ruled out the ability to sync your iPhone 5 with a PowerPC Mac as those only ran Mac OS X 10.5.8 Leopard at most. Given that Mac OS X 10.6 Snow Leopard was released in August 2009 and the iPhone 5 was released in 2012, this seems like a reasonable cutoff, especially in the fast-moving world of technology back then.

If you Google this problem, you will find that there are many people online (well, online back in 2012) complaining about this limitation and others confidently making the wrong assertion that this is because of the switch from the 30-pin dock connector to the Lightning connector. However, I was extremely suspicious of this because when I open iTunes 10.6.3 and plug in the iPhone 5, iTunes immediately shows a very nice error that says iTunes 10.7 is required. Furthermore, the iPhone 5 shows up in Xcode! Xcode won’t deploy to the device because iOS is too new, but it shows up and it can see it’s an iPhone 5 and which iOS version it’s running. So I knew that this Lightning issue was not true; clearly, the iPhone was communicating with the Mac even over Lightning.

Given that my iPhone 5 and my iPhone 4s were both running iOS 6.1.3 and one of them would happily sync with iTunes 10.6.3 while one would not, I knew this limitation was artificial. And so began my first reverse-engineering project: Figure out this artificial limitation and eliminate it.

But Why

Why did I spend so much time getting my iMac G4 to sync with an iPhone 5? The answer is that I want to try to use an iOS 6 iPhone as my main iPhone in

What does that mean? Does that mean I won’t have a backup modern iPhone? No, of course I will. It’s not possible to survive in the world without a semi-modern mobile phone. But it will be my backup. I only have a few apps I use on my iPhone and I think I can recreate them for iOS 6 without much issue. But more on that later.

But why not use my iPhone 4s; it’s running iOS 6 as well. Well, the iPhone 5 is the newest iPhone that can run iOS 6, so the performance is much better, and it has 1 GB of RAM which seems insane to me. But more importantly, the iPhone 5 has a widescreen display. Given so much of what I do on the iPhone is YouTube, the lack of widescreen is kind of killer. Also, the iPhone 5 can join 5 GHz Wi-Fi networks, and it has a Lightning connector. Lightning cables are so important because they are plentiful, and I can charge anywhere, even in 2026.

For these reasons I wanted to get my iPhone 5 working on my iMac G4 so I have a full retro sync solution for all of my music, photos, podcasts, etc.

Approach

At first, I thought the mechanism that prevented syncing with the iPhone 5 was a whitelist in iTunes or in MobileDevice.framework. However, after many hours searching both the disk and the iTunes and MobileDevice binaries in Hopper, I was totally failing to find a whitelist of supported devices (Spoiler Alert: There isn’t one). So I had to change techniques. I had to try to debug iTunes live in GDB.

I had never done disassembly or GDB on an app I didn’t make before. It’s definitely an interesting process. I used a ton of Gemini to get this done (But I assume any AI will work). Gemini can’t think for you. But it can help you with syntax and with knowing which functions in Core Foundation to set breakpoints on. But yeah, it can also totally lead you astray. There were times when I was outright scolding it to try to get it back on the right path.

In the following few sections, I will walk you through how I defeated the iTunes version restriction for the iPhone 5. Considering how simple the fix ended up being, there are probably a lot of people out there wondering why no one did this 12 years ago when the iPhone 5 was new (me included).

0. Run iTunes with GDB

I used GDB to launch and debug iTunes. I used custom GDB files to set breakpoints and inspect the data flow between the iPhone and iTunes.

In every section below, I will include the GDB file so you get an idea of how it works. To use the file, use the -x command in GDB.

gdb -x ~/Desktop/myfile.gdb /Applications/iTunes.app/Contents/MacOS/iTunes

1. Defeat PTRACE

iTunes operates in a very defensive way. It’s not surprising given this is one massively complex codebase and it deals with a lot of DRM content, purchasing, etc. For this reason, iTunes does frequently use ptrace to check if it’s connected to a debugger, and if so, it just quits. So the first thing I had to figure out how to do was bypass this check.

It turns out it’s pretty easy. I set a breakpoint on the ptrace function and then forcefully return 0. With that simple trick, it worked. With this in place, iTunes happily runs while connected to the debugger

# Set a breakpoint on ptrace
break ptrace
commands
  # Optional, tells GDB to not print that the breakpoint was hit
  silent
  # Trick iTunes by forcing ptrace to return 0, no debugger attached
  return 0
  # Automatically continue so that the debugger doesn't pause
  continue
end

# Tells GDB to run the executable after it reads the file
run

2. Inspect Every String Created

I had very little to go on at this point. I had already searched the binaries in Hopper thoroughly and I could not find any hard-coded references to any iPhone identifiers. I had also exhaustively searched the whole filesystem for references to iPhone identifiers. I was trying to find the whitelist for supported devices somewhere, but I just couldn’t find it.

So I dropped down to the lowest common denominator in GDB. “What if I just print every string that iTunes makes and see if I can find the whitelist in there?” The short answer is I did not find the whitelist, but when observing the strings flowing through the system, I noticed a lot of XML, especially after I plugged in my phone. Perhaps this XML contained something interesting; perhaps indeed

break ptrace
commands
  silent
  return 0
  continue
end

# Set a breakpoint on Core Foundation function that creates strings
fb CFStringCreateWithBytes
commands
  # Print register 4 which contains the raw data bytes
  x/s $r4
  continue
end

run

3. Inspect Every Dictionary Created

Now that I was seeing XML get passed around, I thought this could be the key. What is in all of this XML? I decided I would inspect it and see if there was anything interesting. It turned out to be insanely interesting because once I plugged in any iPhone, iTunes and the iPhone would immediately start an elaborate handshake via property lists. A ton of information was exchanged between them. This included the most critical piece!

It turns out that the iPhone was the one telling iTunes which version of iTunes was required. THERE WAS NO WHITELIST!

Note that this file introduces a new GDB technique that Gemini showed me. When you start printing all of these strings to the console, the app slows down significantly. So at the beginning of the file, we set all the breakpoints we need. Then at the end, we disable the one we don’t want (Breakpoint 2). Then in a different breakpoint we re-enable that breakpoint.

With this technique we don’t need to print every XML iTunes creates when it boots up. Rather, we wait until the iPhone is plugged in AMDeviceConnect and then enable the XML printing breakpoint.


break ptrace
commands
  silent
  return 0
  continue
end

# Set a breakpoint on Core Foundation function that 
# creates a dictionary from property list data
fb CFPropertyListCreateFromXMLData
commands
  # Get a pointer to the data (TODO: Is this needed???)
  set $bytes = (char*)CFDataGetBytePtr($r4)
  printf "%s\n", $bytes
  continue
end

# Set a breakpoint on the MobileDevice.framework function that 
# starts the iTunes <-> iPhone Handshake to enable the 
# CFPropertyListCreateFromXMLData breakpoint
fb AMDeviceConnect
commands
  # Re-enable breakpoint on CFPropertyListCreateFromXMLData
  enable 2
  continue
end

# Disable breakpoint on CFPropertyListCreateFromXMLData to improve performance. 
# Once AMDeviceConnect is hit, the breakpoint will be re-enabled
disable 2

run

The XML is huge, so I won’t put it all in here. But below is a sample, including the key we are interested in MinITunesVersion. Also, if you notice, it says MinMacOSVersion is 10.5.8 which means if Apple had released iTunes 10.7 for 10.5.8, it would have worked without hacking. But I suppose what this means is you might be able to sync with iTunes running on 10.4 if you also changed the MinMacOSVersion key in the iTunes binary. Of course, I have not tried this so it might not work.

  GeniusConfigMaxVersion
  20
  GeniusConfigMinVersion
  1
  GeniusMetadataMaxVersion
  20
  GeniusMetadataMinVersion
  1
  GeniusSimilaritiesMaxVersion
  20
  GeniusSimilaritiesMinVersion
  1
  HomeScreenIconColumns
  4
  HomeScreenIconDockMaxCount
  4
  HomeScreenIconHeight
  57
  HomeScreenIconRows
  5
  HomeScreenIconWidth
  57
  HomeScreenNewsstand
  
  IconFolderColumns
  4
  IconFolderMaxPages
  1
  IconFolderRows
  4
  IconStateSaves
  
  KeyTypeSupportVersion
  492
  MinITunesVersion
  10.7.0
  MinMacOSVersion
  10.5.8
  NeedsAntiPhishingDB
  
  OEMA
  1
  OEMID
  0
  PhotoEventsSupported
  
  PhotoFacesSupported
  
  PhotoVideosSupported
  
  PlaylistFoldersSupported
  
  PodcastsSupported
  
  RentalsSupported
  
  Ringtones
  
  ScreenHeight
  1136
  ScreenScaleFactor
  2
  ScreenWidth
  640
  SupportedKeyboards
  
    ar
    bg_BG
    bo
    ca_ES
    chr

4. [Failed] Use GDB to Replace the MinITunesVersion

Now that I knew exactly where the XML data was flowing through the system, I thought I would try to change it in-flight with GDB and iTunes would be none the wiser. However, this proved to be extremely difficult. Gemini walked me through all sorts of possibilities. The one I thought would be the most straightforward was setting a breakpoint on CFDictionaryGetValue and CFDictionaryGetValueIfPresent. I could then check if the key was MinITunesVersion and either return 10.6.3 or null. However, this turned out to be very complex because CFString/NSString are a class cluster and have many underlying data types. From a developer’s perspective, there is no difference, but when you are in GDB, you need to account for every possibility in order to compare the string data. Also, if you use a high-level compare or print function like CFShow or CFStringCompare, that allocates new memory and that would cause iTunes to crash randomly as it’s not really safe to do that in the debugger.

Note that even though the code snippet below is small, at this stage I spent so many hours with Gemini trying to get a working solution that would patch the MinITunesVersion in flight using GDB.


break ptrace
commands
  silent
  return 0
  continue
end

# Set a breakpoint on Core Foundation function that 
# fetches the values from a dictionary using a key
fb CFDictionaryGetValue
commands
  # Even this simple command to print the key would eventually crash iTunes
  call (void)CFShow($r4)
  continue
end

fb AMDeviceConnect
commands
  enable 2
  continue
end

disable 2

run

5. Replace the Key Directly in the iTunes Binary

It was only when this solution was not working that I started to use plain old-fashioned grep to search not only the entire filesystem on my iMac G4 but also on my iPhone 5 for the key MinITunesVersion. I actually found several interesting binaries on the iPhone 5 this way, but I have yet to look into them.

But on the iMac G4, it of course showed the plain-old iTunes binary contained this key. That is when I thought, perhaps I can just change the key in the binary and call it a day. Then iTunes would just use the wrong key when querying the Property List provided by the iPhone. This could of course cause a crash if the key was required and expected by iTunes. However, I found that when I watched the XML handshake between iTunes and my iPhone 4s, MinITunesVersion was not present. This meant that iTunes was probably considering this key optional, so it was safe to change it

And that’s exactly what happened. I opened the iTunes binary in a hex editor, searched for MinITunesVersion, changed it to MinITuMesVersion, and clicked “Save.” After relaunching iTunes, I plugged in my iPhone 5 and it just showed up in iTunes with no fuss at all. Everything syncs just fine. I couldn’t believe it!

6. [Future Work] iPhone Artwork

I want to get the correct artwork showing for the iPhone model in iTunes but right now it shows a blank. I tried manually installing the artwork files from iTunes 10.7 but that did not work (it also did not break anything). After doing some digging in Hopper, it looks like iTunes has a huge function that was probably code-generated where it selects the images. I tried for a bit to get it working, but I had to stop as it’s a low priority.

But maybe one of these days…

How to Develop Original iPhone Apps in 2025

2025-12-09T00:00:00+00:00

PowerPC Setup	Xcode Screenshots

Table of Contents
Overview
Tutorial: Prepare the Computer to Sign iPhone Apps (Apple Developer Portal)
Tutorial: Prepare the iPhone to Ignore the Signature (Jailbreak)
Congratulations!

Overview

In this article we will cover how to deploy apps from Xcode to an original iPhone running iPhone OS 2 or 3 in 2025. This will also work with iPhone 3G, iPod Touch (1st Generation), and iPod Touch (2nd Generation). This is the second article in the "Enabling iPhone Development for PowerPC Macs" series but this no longer requires a PowerPC Mac. You can use any Mac running 10.7, 10.6, or 10.5 that has Xcode 3 or 4 with the iPhone SDK installed, including a virtual machine (if you still have an Intel Mac).

There are a lot of fiddly steps, but I think it’s important to remember that this is no different than what every iPhone developer had to do back in 2008. Now Xcode has been enhanced so much that it’s all done for you. But back then, these were totally normal steps.

Caveats

This requires an Apple Developer account (I am unsure if a free one will work or not)
This requires a jailbroken iPhone or iPod Touch

I think it is possible to do this without a developer account. I found a Stack Overflow post covering how to do it. However, they all require the use of a jailbreak tool called ldid. I have not been able to find a copy of ldid compiled for PowerPC Macs. It might be possible to build from source, but I have not tried.

Approach

We are going to prepare Xcode to sign iPhone apps using the Apple Developer Portal. Then we are going to prepare the iPhone to ignore the signature via a jailbreak. This approach seems strange, but there are two sides of the equation. Xcode will not complete the build process for iPhone apps that are intended for the device without proper signatures. But then, these old iPhone OSes are so out of date that they no longer contain valid certificate authorities to trust those signatures, resulting in them refusing to launch the signed apps, thus requiring the jailbreak.

In this tutorial we are going to be basically living in the “Organizer” in Xcode

Modern Xcode also has a window called Organizer, but it is significantly different now. So you may want to check out "Professional Xcode: Chapter 22 Using the Organizer" on Archive.org to read more about Organizer. It actually has many capabilities you would not expect such as capturing screenshots from the device. The book also covers provisioning your iPhone, admittedly in less detail than this tutorial.

Prepare the Computer to Sign iPhone Apps (Apple Developer Portal)

Authority: Install the latest Certificate Authorities into your Mac
Certificate: Create iPhone Development Signing Certificate
Identity: Create Wildcard iPhone App Identity
Device: Add iPhone Device to Portal
Provision: Create Provisioning Profile (Combines Steps 2, 3, and 4)
Info Plist: Edit the Info.plist and Build Settings of Your App

Prepare the iPhone to Ignore the Signature (Jailbreak)

Jailbreak: Restore and jailbreak iPhone using Legacy iOS Kit
Cydia: Install the AppSync Tweak in Cydia
Provision: Install the Provisioning Profile on Device
Run: Run App on Device

If anyone has advice on how to either not require the developer account to get Xcode to deploy without a proper signing certificate OR anyone knows how to get the iPhone to launch the properly signed app without a jailbreak, please let me know, so I can enhance the tutorial. I think it is frustrating to BOTH need a developer account AND need a jailbreak. It should be one or the other, not both.

System Requirements

A Mac or Virtual Machine that is running Mac OS X 10.7, 10.6, or 10.5
A Mac with USB 2.0 (it might work with USB 1.1 but no promises)
Xcode 4.x.x, 3.2.x, or 3.1.4 (The screenshots in this article are for Xcode 3)
Original iPhone, iPhone 3G, iPod Touch (1st Generation), iPod Touch (2nd Generation)
Device running iPhone OS software 3.1.3 or lower
- These devices can easily be downgraded using Legacy iOS Kit
- Legacy iOS Kit requires an Intel or Apple Silicon Mac or a Linux computer

Tutorial: Prepare the Computer to Sign iPhone Apps (Apple Developer Portal)

1. Authority: Install the Latest Certificate Authorities on Your Mac

Before any of this will work, we need to make sure your ancient version of Mac OS X is loaded with the latest Apple Certificate Authorities and Intermediate Certificates that Apple uses for signing its development certificates.

Apple PKI	Open Panel

Open Apple’s PKI page
Download the following certificate files. Depending on your browser you may need to hold the Option key while clicking on them to download the certificate files.
1. “Apple Inc. Root”
2. “Apple Root CA - G2 Root”
3. “Apple Root CA - G3 Root”
Double-click them one by one. In the Keychain Access open panel, it will give you a choice of which keychain to add them to. Choose the System keychain, not the Login keychain.
Now do the same for the Worldwide Developer Relations intermediate certificates.
1. Worldwide Developer Relations - G2
2. Worldwide Developer Relations - G3
3. Worldwide Developer Relations - G4
4. Worldwide Developer Relations - G5
5. Worldwide Developer Relations - G6

Now your Mac should trust the certificates issued by Apple.

2. Certificate: Create iPhone Development Signing Certificate

This is the most tedious part. You should probably make a folder on your system for storing all the output of this step, so you can zip it all up at the end as a backup. This should all be possible on your vintage Mac via AquaFox (PowerPC) or ArcticFox (Intel), but I chose to use my modern Mac to do all of the Apple Portal stuff. This means I needed to transfer files back and forth between the old system and the new system.

A. Make Your Certificate Signing Request

Select Apple CA	Certificate Signing Request

Follow the instructions on this page to make a Certificate Signing Request. Note that these instructions did not work for me at first. The Assistant said it had made my request and saved it to the Desktop, but it had not. To resolve this, I went into the System keychain and selected the Apple Root CA before starting the Assistant. I am not sure if it matters which certificate you select, but it seems like you need to select something first.

The way I could tell that it was going to work was that the assistant displayed the checkbox in the UI that says “Let me specify key pair information.” When that checkbox was present, then the assistant would actually make the Certificate Signing Request file.

B. Make a Signing Certificate

Prompt 1	Prompt 2	Certificate Download

Open Apple Developer Portal - Certificates and click the + button next to Certificates
Follow the prompts, all the default options are fine
Download the certificate when you get to the end

C. Add the Signing Certificate to the Keychain

All Items	My Certificates

Double-click to add the Signing Certificate to the Login keychain. Note that the Signing Certificate MUST appear in the “My Certificates” section of Keychain Access. If you see it in the “All Items” section but not in the “My Certificates” section, then Xcode will not properly see it.

This happened to me and I used Gemini to help me fix it. You can see the full conversation here, but the summary is that you need to export the private key as a P12 file, then delete all three certificates from Keychain, then re-add the P12 file and then re-add the Signing Certificate. That did it for me. I have no idea why.

3. Identity: Create Wildcard iPhone App Identity

Prompt 1	Prompt 2	Prompt 3	Prompt 4

Now you are going to create a “wildcard” App Identity. Wildcard means we just need to specify the base part of the bundle identifier and the part where the app name goes is just an *. If you are an iOS developer, you may already have an established base name. But if not, you can just use the Bonjour name of the Mac you are running Xcode on. I will do that and so it will be local.IchigoDaifuku.*. You will need to type this name into the Info.plist of every app you make, so make it something easy to remember.

Open Apple Developer Portal - Identifiers and click the + button next to Identifiers
Follow the prompts, all the default options are fine
When it asks you for the bundle identifier, click the “Wildcard” radio button and type in your identifier
Click “Register”
There is nothing to download in this step, so you can move to the next step

4. Device: Add iPhone Device to Portal

Device Error	Copy Device ID	Developer Portal

Now you are going to add your device to the Apple Developer Portal so that we can generate a provisioning profile in the next step.

In Xcode, choose Window→Organizer and then plug in your device
If you see the Device Error above, then this version of Xcode is not compatible with your device or the OS that’s installed on it.
Right-click the device name in the sidebar and choose “Copy Device Identifier”
Open Apple Developer Portal - Devices and click the + button next to Devices
Go through the prompts and paste in the Device ID when requested
There is nothing to download after this step, so you can move on to provisioning

If you got the error above that your device is not compatible, please verify your device version, the software version, and the Xcode version. These all need to be compatible to move on. If it’s an iPhone 4 or lower, then the device software can easily be downgraded via Legacy iOS Kit.

5. Provision: Create Provisioning Profile (Combines Steps 2, 3, and 4)

Prompt 1	Prompt 2	Prompt 3	Prompt 4	Prompt 5	Prompt 6	Organizer

Now you are going to create the provisioning profile. This step combines the signing certificate (Step 2), the app identifier (Step 3), and the device identifier (Step 4) into the final step. Please be very careful when going through the prompts on the Apple Developer Portal as any mistake will make the provisioning profile invalid.

Open Apple Developer Portal - Profiles and click the + button next to Profiles
Prompt 1: Choose “iOS App Development”
Prompt 2: Choose the App Identifier you made in Step 3
Prompt 3: Choose the Certificate you made in Step 2. The names can be pretty vague but I think the bottom one is the newest
Prompt 4: Choose the Device you added in Step 4
Prompt 5: Give the Profile a name
Prompt 6: Download the provisioning profile
Organizer: In Xcode, choose Window→Organizer. In the sidebar, select Provisioning Profiles and then drag the profile from the Finder into the Organizer
Now you can ZIP up all the uploads and downloads created during this part of the tutorial for safekeeping, in case they are ever needed again

6. Info.plist: Edit the Info.plist and Build Settings of Your App

Info.plist	Build Settings 1	Build Settings 2	Build and Go	No Device Error

Now you are going to edit the Info.plist and the build settings of your application. If you don’t have an application, you can just create one from the templates under File→New Project. And yes, you will need to do this any time you create a new application project.

In Xcode, open Info.plist and change the bundle identifier to match Step 3. Type Command + S to save the file
Open the Build Settings by selecting the project file at the top of the Groups & Files pane and then click on Info in the toolbar
In the info panel, click on the Build tab and then make sure the Configuration and Show dropdowns say “All”
In the Build Settings panel, look for Code Signing Identity, and choose the provisioning profile you created in Step 5 and then close the info panel
Make sure there is no device connected, then choose Device from the Overview dropdown and then click Build and Go
At this point, you might see a Keychain access permission prompt; choose “Always Allow”
Lastly you should see an error appear that says “No provisioned iPhone OS device is connected”

If you receive the “No provisioned iPhone OS device is connected” error, you have succeeded, congratulations! You have just gone through the really tedious task that Apple created for all iPhone developers back in 2008. Now Xcode is 100% ready to deploy your custom apps to a real iPhone!

If you see a different error, like a build or signing error, then you have a different problem that you need to troubleshoot before you can move on.

Tutorial: Prepare the iPhone to Ignore the Signature (Jailbreak)

This is the part of the tutorial that an iPhone developer would not have had to do in 2008. I am not quite sure the reason, but iPhone OS 3.1.3 no longer trusts the signature we just worked so hard to enable in Xcode. Yes, we had to do it because Xcode will not deploy apps to a device without a valid signature. But if you try to plug in your device and deploy to it right now, you will get an error telling you that the app could not be installed because there were certificate issues and it suggests checking the date and time on the phone. I think what has happened is the Certificate Authorities that Apple used in 2008 have expired since then and are no longer valid. I tried installing the CAs from Step 1 of this tutorial on the phone, but I still got the same error.

It’s OK though, because honestly, these old devices are pretty much bricks without a jailbreak. Also, jailbreaking is so incredibly easy now thanks to Legacy iOS Kit by LukeZGD. If you use this tool successfully, you should definitely buy him a coffee because the script is amazing! It even helps you enter DFU mode with exactly timed instructions.

1. Jailbreak: Restore and Jailbreak iPhone using Legacy iOS Kit

Main Menu	Select OS	Download IPSW	Start Restore	Restore

I will provide the instructions for performing a restore and jailbreak, which will erase everything on the device. However, if your device is a time capsule, and you do not want to erase it, I totally understand. Legacy iOS Kit can also just jailbreak it for you. Please see the documentation.

On a modern-ish Intel or Apple Silicon Mac, open Terminal: cd Downloads
Clone Legacy iOS Kit: git clone https://github.com/LukeZGD/Legacy-iOS-Kit.git
cd into the directory: cd Legacy-iOS-Kit
Run the setup script: ./restore.sh
Plug in your device and then run the script again: ./restore.sh
Follow the onscreen prompts to restore
1. Please read the prompts carefully and see the screenshots above for a full visual walkthrough
2. Note that the script will offer to download the latest version of the OS for you, but if you want to select your own version you can download it from IPSW.me

The device should now be restored and jailbroken. If you can’t unlock it (meaning it is stuck at the slider that says Slide for Emergency), then run the script again and it will have an option to attempt activation. If there is a SIM card in the device, this should work without the Hacktivate option. But sometimes you have to try the “lighter” activation thing two or three times.

2. Cydia: Install the AppSync Tweak in Cydia

Add Source	Install 1	Install 2	Install 3	Install 4	Install 5

Now you will be installing a special tweak for the iPhone called AppSync. This tweak will prevent the process called installd from checking for signatures when apps are installed. This is critical to installing apps from iTunes, Xcode, or even Legacy iOS Kit as this one process checks all of them for a valid signature before installing.

There is a different version of AppSync for different iOS versions, so see the Legacy iOS Kit Documentation for full details. In this tutorial, I will be showing this for iPhone OS 3.1.3.

Open Cydia: On first launch, Cydia may need to do a one-time setup and then restart
Show Sources: Tap on the Sources tab and wait for it to refresh (it could take a while)
(Optional) Delete Bad Sources: For sources that failed to refresh, delete them. They will have no icon and if you tap on them, they will have no packages
Add Source: Tap the “Edit” button at the top right and then tap “Add” at the top left and type http://ios3.party
Install AppSync: Tap “iPhone OS 3 Party,” tap “All Packages,” tap “AppSync for OS 3.1,” tap “Modify,” then tap “Install,” and lastly tap “Confirm”
Restart: After you see the button that says “Return to Cydia”, you can tap it and then restart the device

3. Provision: Install the Provisioning Profile on Device

Add Profile	Profile Installed	Device Verify

The last step before running an app is to connect it to your vintage Mac and ask the Mac to use it for development.

Organizer: In Xcode, choose Window→Organizer and then plug in your device
Use for Development: Select your device in the sidebar and then click “Use for Development” (sorry, no screenshot because this is a one-time action)
Add Profile: Under the Provisioning section, click the + button to add your provisioning profile
Device Verify: On your device, open Settings, then tap General, then tap Profiles to verify your provisioning profile was installed

4. Run: Run App on Device

Xcode Breakpoint	iPhone Paused	Xcode Paused	iPhone Running	Xcode Error

You’re probably pretty tired by now, but hang in there, we are about to finally achieve our goal! Running your custom app on your vintage iPhone with the full debugger and all the goodies.

Open your app project in Xcode, then follow numbers 1 through 5 in the Xcode Breakpoint screenshot above:
1. ① Open main.m
2. ② Set a breakpoint on or before UIApplicationMain (click in that little gutter area)
3. ③ Make sure the Overview menu is set to run on Device
4. ④ Click to change to the debugging view
5. ⑤ Click Build and Go
Wait 30–60 seconds and you should see your app launch on your phone and it will pause at the launch image
In Xcode, you will see the breakpoint was hit; click the Continue button
On your phone, your app will now be running
If you see the error in the screenshot above with the selected console output, that means that AppSync from the previous step is not installed or not working properly and the iPhone is still checking signatures

Congratulations!

You now have a setup that can build and deploy apps to your vintage iPhone! Please enjoy the process of making vintage apps and working with old-school Objective-C. It’s kind of a pain in the butt, but I think you will enjoy its simplicity and flexibility.

If you want to run MameDaifuku, my sample app that lists out some build and runtime information, you can clone or download it from GitHub. https://github.com/jeffreybergier/MameDaifuku

Enabling iPhone Development for PowerPC Macs

2025-12-04T00:00:00+00:00

PowerPC Setup	Xcode Screenshots

Table of Contents
Overview
Tutorial

Overview

Apple always officially required an Intel Mac to do iPhone app development, but I figured out how to get the iPhone OS 3.1.3 SDK installed for developing Original iPhone and iPhone 3G apps on your PowerPC Mac. This builds upon the work of whoever in the community created the custom installers and scripts found on Macintosh Repository. This hack relied on the fact that even though Apple required Intel Macs for iPhone development, they actually shipped universal binaries for the iPhone SDK up until iPhone OS 2.2.1 SDK.

But the 2.2.1 SDK is quite limited and the iPhone really started to come into its own with the 3.0 and higher SDKs. These included critical improvements like Core Data, AVFoundation, MediaPlayer, and others. So I started to look into whether it was possible to get the new SDK on a PowerPC Mac as well. And to my surprise, it is possible! It will even deploy to a real iPhone running 3.1.3.

In this document I will walk you through how I did it.

Caveats

While this does work, there are some fundamental limitations:

iPhone Simulator only runs iPhone OS 2.2.1
- This cannot be overcome because Apple only shipped universal PowerPC and Intel binaries for iPhone OS 2.2.1 and lower
You must have a developer account if you want to deploy to a device
- There are probably workarounds, but I just did everything the official way
Your iPhone must be jailbroken if you want to deploy to a device
- I think this is due to expired certificate authorities on iPhone OS 3.1.3, but I am not 100% sure
This Xcode 3 is very old and is not much different than the original Project Builder
- Xcode would not get its new UI style that is still used today until Xcode 4, which only runs on Mac OS X 10.6 Snow Leopard, which is Intel-only
- The SDK does not support many basic features such as Automatic Reference Counting

Approach

Install Xcode 3.1.4
Force install the iPhone OS 3.1.3 SDK
Force install iPhone Simulator.app from the iPhone OS 2.2.1 SDK
Patch some installed files so everything runs on PowerPC

System Requirements

PowerPC Mac
Mac OS X Leopard 10.5.8 with all updates installed
To run on a real device
- USB 2.0 (it might work with USB 1.1 but no promises)
- Original iPhone, iPhone 3G, iPod Touch (1st generation), iPod Touch (2nd generation)
- Device running OS software 3.1.3 or lower
  - These devices can easily be downgraded using Legacy iOS Kit

Tutorial

0. Download Everything

Internet Archive	Macintosh Repository	All Downloaded

If you use AquaFox, you can actually do the downloads directly on your PowerPC Mac. But of course, you can also download everything on a modern computer and transfer it over to the Mac via AFP or SCP.

iphone_sdk_3.1.3_with_xcode_3.1.4__leopard__9m2809a.dmg (Internet Archive)
1. Direct Link in case you can’t find the exact right build 9m2809a
iPhone_SDK_for_iPhone_OS_2.2.1_PPC.iso (Macintosh Repository)
1. Also available on Macintosh Garden
iPhone313PPCInstaller.zip (This website)
1. Do not download iPhoneSDK.dist_.zip or iPhonePPCEnabler.dmg on Macintosh Repository as these are for the 2.2.1 SDK only
Unzip iPhone313PPCInstaller.zip

1. Install Xcode 3.1.4

Mount the iphone_sdk_3.1.3_with_xcode_3.1.4__leopard__9m2809a.dmg and open the installer file to do a normal install of Xcode. I selected all possible options, but you should only need the basic developer tools package. The installer WILL NOT let you select the iPhone SDK packages. That’s OK; we will do that in the next step. This took about 30 minutes on my 1.25 GHz iMac G4 with a 1 TB SSD, so please be patient if your system is slower and/or does not have an SSD.

Note that you must install in the default location /Developer

2. Force install the iPhone OS 3.1.3 SDK

Verify that the iPhone SDK disk image is mounted with the correct name
1. Open Terminal and type ls -al /Volumes
2. You should see iPhone SDK, not iPhone SDK 2 or some other name. If it’s not called exactly iPhone SDK then the installer will fail.
Open iPhone313PPCInstaller.mpkg and run the installer
1. This installs the entire iPhone OS 3.1.3 SDK except for simulators higher than 2.2.1. Those simulators are Intel only and therefore will never work on a PowerPC Mac.
Unmount the iPhone SDK disk image

At this point you will have a fully working Xcode install and you will even be able to create new iPhone projects. However, there are three problems that need to be fixed:

iPhone Simulator.app will not open because it is Intel only
The copy of ld for the iPhone SDK is Intel only
Interface Builder cannot open XIBs for the iPhone because its plugin is Intel only

If you want to confirm that iPhone Simulator is Intel only you can use the following terminal command:

ichigodaifuku:~ me$ lipo -archs /Developer/Platforms/iPhoneSimulator.platform/Developer/Applications/iPhone\ Simulator.app/Contents/MacOS/iPhone\ Simulator 
i386

You can use lipo -archs to check any binary on your system to see if it is universal.

3. Force install iPhone Simulator.app from the iPhone OS 2.2.1 SDK

One of the included files is iPhone221PPCInstaller.mpkg. This file was originally provided on Macintosh Repository but I customized it to only install one small part of the iPhone OS 2.2.1 SDK instead of the whole thing. It only installs the iPhoneSimulatorPlatform.pkg, which installs the universal binary version of the iPhone Simulator as well as the Interface Builder plugin for iPhone XIBs.

Unmount the iPhone SDK disk image (if you didn’t do it already as instructed in the previous step)
Mount iPhone_SDK_for_iPhone_OS_2.2.1_PPC.iso
Verify that the iPhone SDK disk image is mounted with the correct name
1. Open Terminal and type ls -al /Volumes
2. You should see iPhone SDK, not iPhone SDK 2 or some other name. If it’s not called exactly iPhone SDK then the installer will fail.
Open iPhone221PPCInstaller.mpkg and run the installer. This installs:
1. iPhone Simulator app that is a universal binary
2. Interface Builder plugin for reading iPhone XIBs that is a universal binary
3. Runs a script that patches the xcspec files
  1. There is no credit for this script on Macintosh Repository
  2. If you want to know more about what it patches, see this blog post by Chris Hardie

4. Patch ld

ichigodaifuku:~ me$ chmod +x /Users/me/Desktop/iPhoneSDKInstall/iPhone313PPCldPatch.sh 
ichigodaifuku:~ me$ sudo /Users/me/Desktop/iPhoneSDKInstall/iPhone313PPCldPatch.sh 
--- iPhone OS 3.1.3 PPC Enabler LD Patch Post-Install Script Started ---
Verifying files: SUCCESS.
Target linker (/Developer/Platforms/iPhoneOS.platform/Developer/usr/bin/ld) and source linker (/Developer/usr/bin/ld) found.
COMMAND: Backing up Intel 'ld' binary to /Developer/Platforms/iPhoneOS.platform/Developer/usr/bin/ld.backup.intel
COMMAND: Copying functional PPC 'ld' over the Intel one...
COMMAND: Setting executable permissions for /Developer/Platforms/iPhoneOS.platform/Developer/usr/bin/ld
SUCCESS: PPC 'ld' copied and permissions set.
--- iPhone OS 3.1.3 PPC Enabler LD Patch Post-Install Script Completed Successfully ---
ichigodaifuku:~ me$ 

The normal version of ld that comes with Xcode is a universal binary but the version that comes with the iPhone SDK is Intel only (for some reason). It’s the only Intel-only part of the SDK, as far as I can tell. I provided a script to patch ld to make it easy, but all it does is back up the original and then copy the version from Xcode into the iPhone SDK’s location.

I wanted to make the script run automatically at the end of Step 2 but I could not figure out how to insert the script into the installer. If you know how, please let me know and I will improve iPhone313PPCInstaller.mpkg.

Open Terminal
Change the permissions to make the script executable (this is not preserved by the ZIP file)
1. Type chmod +x ; note the space at the end
2. Drag iPhone313PPCldPatch.sh into the terminal window
3. Press the return key to set the permissions
Execute the script with admin privileges
1. Type sudo ; note the space at the end
2. Drag iPhone313PPCldPatch.sh into the terminal window
3. Press the return key to run the script
The terminal output should look like the code snippet above
Restart your computer

If you want to manually verify it worked, you can use the lipo command again:

ichigodaifuku:~ me$ lipo -archs /Developer/Platforms/iPhoneOS.platform/Developer/usr/bin/ld.backup.intel
i386
ichigodaifuku:~ me$ lipo -archs /Developer/Platforms/iPhoneOS.platform/Developer/usr/bin/ld
i386 ppc7400
ichigodaifuku:~ me$ 

5. Run an App in the Simulator

Step 2	Step 3	Step 4	Step 5

We can’t deploy to device yet as there is more work to do, but you should make a sample app and make sure it launches in the simulator.

Open Xcode and select File→New Project
Choose any iPhone project you like but I chose “Tab Bar Application”
There is a toolbar item labeled “Overview” where you can change the deployment target from Device to Simulator
Now open one of the XIBs in Interface Builder to make sure that is working. Change some text so you know that the app runs properly when changed
Click Build and Run to compile the app, launch the Simulator app, and launch your new app

6. (Coming Soon) Run an App on Device

In the next episode, we will go through the steps needed to get an app running on the device. Remember, this is before Xcode could manage signing for you, so you will need to do it the old-fashioned way

MathEdit for OpenStep

2025-10-06T00:00:00+00:00

NS is for NextStep

As Cocoa developers, we were always taught that the NS in NSString, NSDictionary, NSArray, etc., stands for NeXTSTEP. So I thought, “What is it like to build an application for NeXTSTEP?” So I decided to try it! I got an OpenStep 4.2 Virtual Machine up and running, installed Project Builder (the precursor to Xcode) and got to work. MathEdit is the result.

Lessons Learned

The Good

OpenStep’s Foundation and AppKit frameworks are remarkable in that they are extremely complete even way back in 1996 (remember Mac OS X 10.0 Cheetah was released in 2001). If you ignore NIBs, then the code from OpenStep just works in OS X even to this day. Yes, there are many deprecation warnings, but all of the APIs work without issue. And yes, it means NSApplication, NSTableView, NSWindow, NSButton, NSMenu, the responder chain, etc all work exactly the same as they do now.

The Bad

However, there is a lot of core functionality missing. Networking for example. NSData will download things for you when you give it an internet path, but this has all the pitfalls of modern NSData. It’s single-threaded, blocking, has no progress, etc. If you want anything more than that you need to drop down to BSD Sockets. AppKit is missing basics like NSToolbar and NSDocument. Foundation is missing basics like NSError and NSURL, which kind of explains why there are all those duplicate methods with NSURL and NSString and with NSError and without NSError.

The Ugly

Lastly, there is the really hard stuff. Objective-C before “2.0” as Apple called it is pretty painful. That said, Objective-C 2.0 did not come to Mac OS X until 10.7, so that’s pretty late in OS X history. But still, we are talking about the most basic features missing:

Automatic Reference Counting
Fucking Block Syntax
Property Syntax
Dot Syntax
Grand Central Dispatch
Collection Literals

The other major pain point is Nibs. While OpenStep Nibs do work in early versions of OS X, Apple had a bad habit of changing the Nib format, XIB format, and then just refusing to load older Nibs for security reasons over the years. So the only way to make an app that is compatible across history is to not use Nibs… and unlike on iOS, AppKit really does not like this. I spent a lot of time getting memory management to work properly in early versions of OS X that just ABSOLUTELY ASSUMED you were using Nibs. I did get it to work, but this was like days and days and days of research. Also, I had to learn the secret trick to set the Application Menu which did not exist in OpenStep.

Features

MathEdit is basically like Math Notes from Apple. It’s a normal text editor like TextEdit, but if you type in a mathematical formula in the text, it automatically parses it and solves it for you. It makes extensive use of NSDecimalNumber and NSTextAttachment to do this. NSTextAttachment in particular is the star of the show. It still always shocks me that this was missing from iOS until iOS 7 even though it was in Mac OS X and even OpenStep before that. It is such a powerful way to enhance your text documents.

Caveats

I honestly don’t use MathEdit all that often. It is on all my Macs including my vintage ones and I think it is a cool proof of concept. But I don’t think it’s much more than that. But if you want to try it out for yourself, grab a build for your favorite Mac and give it a try.

https://github.com/jeffreybergier/MathEdit

Retro Software Update Server

2025-09-09T00:00:00+00:00

A guide on setting up an Apple Software Update Server mirror in case Apple ever decides to shut down these old update servers. So far, Software Update still works on Mac OS X 10.4 and above, but Apple already shut down servers for 10.3, 10.2, 10.1, and 10.0 and those can’t be recovered.

If you have an interest in retro Macs, this may be something you would like to set up in case something bad were to happen. This approach works because these servers are still online and still work. If you happen to be reading this 10 years in the future (2035) because Apple shut down the software update servers for PowerPC Macs, then it’s too late. Sorry.

Table of Contents
Who Am I
How Do Software Updates Work on the Mac?
Approach / Guide / Table of Contents
System Requirements
Guide

Who Am I

I’m Jeff, a fan of Mac OS X, NeXT, a software developer, and general retro tech enthusiast. I have other retro tech guides as well as software I have developed for retro Macs, so please check it out.

How Do Software Updates Work on the Mac?

The software update system for Mac OS X 10.4 and higher is actually amazingly simple and flexible. For 10.3 and lower, it was a traditional client/server application. The client would send some information about itself to the server and the server would process this and tell the client what updates it needed. While this seems logical, it also means your servers will be busy processing requests from clients. And as Apple started to become really successful at selling Macs in the early 2000s, the OS X team probably realized that this would fail to scale.

So what did they change? Well, in 10.4 and later, the Software Update Server is nothing more than a huge set of files and a few Update catalogs… one for each version of the OS. These sucatalog files list every update available as well as “distribution” files. These distributions are available for every supported language. They contain the localized description, but they also contain inline JavaScript that will be executed by the client to determine if the update is needed.

What this means is Apple offloaded all of the work of determining which updates it needs from the server to the client. This is great for Apple’s server load, but it also explains why checking for updates can take so long the first time. The client literally needs to download hundreds of distribution files. Yes, they are only a few K each, but then the client also needs to execute the JavaScript for each one.

The other side effect of this system is that now it is easy to mirror the software update server as there is no server-side logic.

Enter Mac OS X Server Software Update Server

Back in the day, Apple included a Software Update Server as part of Mac OS X Server. Apple intended companies to use this to mirror the software updates internally in a company to do 2 things:

Save bandwidth when updating a fleet of Macs
Control which updates were available to the Macs in your company to ensure that you could test compatibility first

This feature is long dead and now Apple facilitates the same control by allowing companies to whitelist or blacklist updates via MDM (Mobile Device Management). This does not create a mirror, but simply tells client Macs to ignore updates. This method does not save bandwidth in your company. But in the modern day, bandwidth is a lot less expensive than it used to be.

When I first started this project, I actually tried to use 10.6 Snow Leopard Server to host the software update server. However, after much troubleshooting, I could not get it to download the updates reliably. It would only download about 1/3 of the updates which is not enough for success. I don’t know why it refused to download them. All it said was there was a suspected security problem and so it refused. ChatGPT suggested that the Apple Software Update Server distributed with their OS had very picky client-side URL validation and if the URLs failed these basic checks, it would not even start the download.

Enter Reposado

Reposado is an open-source project written in Python 2 that replicates the functionality of the software update server. It checks the Apple catalogs, downloads the updates, and then generates new catalogs specific to your mirror. In my experience doing this, it seems to work super well. So this guide will explain how to set this up for you so you can prepare for the very dark day when Apple shuts down these old software updates (which may never come).

Approach / Guide / Table of Contents

Install Git, Homebrew, Python 2
Choose where Software Updates will be mirrored on your server Mac
Configure the Web Server on your server Mac
Configure Reposado on your server Mac
Use Reposado to mirror Apple’s existing software updates to your server Mac
Configure the retro Mac to fetch updates from your server Mac

System Requirements

Server Mac

50 GB+ to dedicate to storing updates
- Even the minimal set for 10.4 Tiger is 20 GB
- Supporting all the way to 10.9 Mavericks takes 200 GB
- ChatGPT says that around 10.11/10.12 Apple started locking down the software update server and it can’t be changed
A normal home network
- This guide assumes you connect all your Macs to the internet with Ethernet or Wi-Fi and they can find each other and connect to each other using Bonjour names.

Retro Mac

Connected to Ethernet or Wi-Fi on the same network as your server Mac
Mac OS X 10.4 or higher

Note that the server Mac can really be any system. Even modern Linux (such as Debian and Ubuntu) automatically identify themselves via Bonjour names. But this guide gives instructions when using a Mac as the server.

Guide

This guide pretty much runs 100% from Terminal. Any text in this special format is a terminal command you can copy and paste.

1. Install Git, Homebrew, Python 2

Git is included as part of the Xcode command line utilities AND these utilities are required for Homebrew anyway.

xcode-select --install

Homebrew is a simple package manager for macOS. It’s easy to install. Just follow the guide on https://brew.sh. Make sure to follow the instructions in the Terminal after installing Homebrew. They are required to make sure that commands you install via Homebrew are easily launchable from the Terminal.

/bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)"

Python 2

This is the difficult one. Python 2 is far out of date, and Homebrew no longer has an easy installer for it. We have to use pyenv, and this basically seemed to build Python 2 from source, which is never fun.

Install pyenv and other tools needed for compiling

brew install pyenv zlib bzip2 readline openssl@1.1

Configure the environment for the Python 2 build

export LDFLAGS="-L$(brew --prefix zlib)/lib -L$(brew --prefix bzip2)/lib -L$(brew --prefix readline)/lib -L$(brew --prefix openssl@1.1)/lib"
export CPPFLAGS="-I$(brew --prefix zlib)/include -I$(brew --prefix bzip2)/include -I$(brew --prefix readline)/include -I$(brew --prefix openssl@1.1)/include"
export PKG_CONFIG_PATH="$(brew --prefix zlib)/lib/pkgconfig:$(brew --prefix bzip2)/lib/pkgconfig:$(brew --prefix readline)/lib/pkgconfig:$(brew --prefix openssl@1.1)/lib/pkgconfig"

Configure your shell to use pyenv

Sorry, you may need to look up the commands for how to use vi or use a text editor you know better, like nano.

vi ~/.zshrc

Paste in the following text and then save and exit:

export PATH="$HOME/.pyenv/bin:$PATH"
eval "$(pyenv init --path)"
eval "$(pyenv init -)"

Compile Python 2

pyenv install 2.7.18

Set Python 2 as the default

pyenv global 2.7.18

Test Python

You should not get an error when running this command:

python --version

2. Choose where Software Updates will be mirrored on your server Mac

The Software Update application on your Mac expects a very specific directory structure and catalog format. Reposado creates this for you. But you still need to decide where on your system this will go and you will also need to configure the web server to use this directory. It is OK to have this on an external drive as the mirror takes a lot of space.

On my system I put everything in

/Volumes/Data/Virtualization/SUS

So the web server document root and Reposado storage are

/Volumes/Data/Virtualization/SUS/www

The Reposado Git clone is

/Volumes/Data/Virtualization/SUS/reposado

The Reposado metadata storage is

/Volumes/Data/Virtualization/SUS/reposado/code/metadata

So you can put everything wherever you like, but this guide assumes this structure.

3. Configure the Web Server on your server Mac

Mac OS X has always included Apache as a web server; it’s just disabled by default. It’s nothing fancy, but it will work for our retro Mac.

Set DocumentRoot to the directory you selected above

sudo vi /etc/apache2/httpd.conf

This file is pretty long, so you have to scroll down to find the DocumentRoot setting. I don’t think you need to change other options, but here are the key ones.

DocumentRoot "/Volumes/Data/Virtualization/SUS/www"

    Options Indexes FollowSymLinks
    AllowOverride All
    Require all granted

Give the web server full disk access

This might not be needed if your directory root is on the boot drive, but I definitely needed it because mine is on an external drive.

Open System Settings→Privacy→Full Disk Access
Click the plus button and enter your admin password
Press ⌘+Shift+G in the file picker and type /usr/sbin/httpd

Turn on the Web Server

sudo launchctl load -w /System/Library/LaunchDaemons/org.apache.httpd.plist

Test the Web Server

Put a test file in the document root. It can be any file, but perhaps a small .txt file is easiest.

Open Safari on your Server Mac and type http://localhost/mytestfile.txt
Open Safari on your Retro Mac and type http://Server-Bonjour-Name.local/mytestfile.txt

Note that step 2 is critical. If you can’t get the website to load on your Retro Mac you won’t be able to update from it either.

4. Configure Reposado on your server Mac

OK, Reposado is where all the magic happens, so let’s get started!

Clone the Reposado Repository

cd /Volumes/Data/Virtualization/SUS
git clone https://github.com/wdas/reposado.git

Configure Reposado

/Volumes/Data/Virtualization/SUS/reposado/code/repoutil --configure

Reposado will ask you for the directories you chose earlier. Note if you drag in the directories from the Finder, it appends a space after them and the developer of Reposado says this will cause errors.

Filesystem path to store replicated catalogs and updates [None]: /Volumes/Data/Virtualization/SUS/www
Filesystem path to store Reposado metadata [None]: /Volumes/Data/Virtualization/SUS/reposado/code/metadata 
Base URL for your local Software Update Service
(Example: http://su.your.org -- leave empty if you are not replicating updates) [None]: Server-Bonjour-Name.local

Configure Reposado (Continued)

Reposado defaults to being a production software update server mirror, which is not what you want because you are setting up a retro software update mirror in case of catastrophe. And you probably don’t want to take 400+ GB of updates for all modern Macs when you could use less than 100 GB to support updating 10.6, 10.5, and 10.4 only.

open /Volumes/Data/Virtualization/SUS/reposado/code/preferences.plist (TextEdit should open)

Your configuration file will look something like this. Copy and paste the keys listed below into your configuration and then customize them as you like:

AppleCatalogURLs to the bare minimum for 10.4 Tiger only (we will expand later after we confirm it’s working)
PreferredLocalizations to include the languages you care about
RepoSyncLogFile so you can see sync progress and verify everything is working

 version="1.0">

	LocalCatalogURLBase
	http://Barely-Regal.local
	UpdatesMetadataDir
	/Volumes/Data/Virtualization/SUS/reposado/code/metadata
	UpdatesRootDir
	/Volumes/Data/Virtualization/SUS/www
	AppleCatalogURLs
    
    http://swscan.apple.com/content/catalogs/index.sucatalog
    http://swscan.apple.com/content/catalogs/index-1.sucatalog
    
    PreferredLocalizations
    
    English
    en
    Japanese
    ja
    
    RepoSyncLogFile
    /var/log/reposado_sync.log
    HumanReadableSizes
    

Create the Log File

Create the log file and make it readable and writable by all users. Normally it would be better to make it readable and writable by the right people, but it’s a single log file. Not really security-critical.

sudo touch /var/log/reposado_sync.log sudo chmod 777 /var/log/reposado_sync.log

You’re Ready to Roll!

In the next section we will fire this thing up and updates will start to stream in!

5. Use Reposado to mirror Apple’s existing software updates to your server Mac

First we will do a test run with the minimal set of Software Update Catalogs that you configured in the previous section. This is about 20–25 GB worth of updates, so depending on how fast or slow your internet connection is, this could take a while. Reposado does not generate the catalogs for your retro Mac to use until it has finished downloading everything, so you need to wait until it finishes. This is why we start with the minimal catalogs.

Tail the log so you can see the progress

Open a new terminal window or tab and run this command to view the log as it gets updated.

tail -f /var/log/reposado_sync.log

Start the Software Update Sync

/Volumes/Data/Virtualization/SUS/reposado/code/repo_sync

That’s it. Now you have to wait for it to download 20 GB or so. You should be able to see progress in the other terminal window with the tailed log file.

What Success Looks Like

The log file will output hundreds of lines, so you may be wondering what success looks like. After downloading all of the files, Reposado will build the catalog files and then report repo_sync run ended. It will look something like this.

Sep 07 17:26:44 Could not get data from dist file: /Volumes/Data/Virtualization/SUS/content/downloads/03/09/061-5359/mxWDL8cXkFTv9pCp8GMFr2bJFXjtqyQbvx/022-4184.English.dist
Sep 07 17:26:46 Could not replicate http://swcdn.apple.com/content/downloads/49/33/061-6390/BYBbD3TFbdpntDts78ddSzDSRpXnGKnQsy/FinalCutPro6.0.6Update.smd: Error 22: The requested URL returned error: 403
Sep 07 17:26:51 Building index.sucatalog...
Sep 07 17:26:51 WARNING: did not add product 061-1688 to catalog index.sucatalog.apple because it has not been downloaded.
Sep 07 17:26:51 WARNING: did not add product 061-2736 to catalog index.sucatalog.apple because it has not been downloaded.
Sep 07 17:26:51 WARNING: did not add product 061-1720 to catalog index.sucatalog.apple because it has not been downloaded.
Sep 07 17:26:51 WARNING: did not add product 041-85067 to catalog index.sucatalog.apple because it has not been downloaded.
Sep 07 17:26:51 WARNING: did not add product 061-6390 to catalog index.sucatalog.apple because it has not been downloaded.
Sep 07 17:26:51 WARNING: did not add product 061-2006 to catalog index.sucatalog.apple because it has not been downloaded.
Sep 07 17:26:51 WARNING: did not add product 061-5359 to catalog index.sucatalog.apple because it has not been downloaded.
Sep 07 17:26:51 WARNING: did not add product 061-2193 to catalog index.sucatalog.apple because it has not been downloaded.
Sep 07 17:26:52 178 products found in http://swscan.apple.com/content/catalogs/index-1.sucatalog
Sep 07 17:26:53 Building index-1.sucatalog...
Sep 07 17:26:54 268 products found in http://swscan.apple.com/content/catalogs/others/index-leopard.merged-1.sucatalog
Sep 07 17:26:55 Building index-leopard.merged-1.sucatalog...
Sep 07 17:26:56 345 products found in http://swscan.apple.com/content/catalogs/others/index-leopard-snowleopard.merged-1.sucatalog
Sep 07 17:27:05 Building index-leopard-snowleopard.merged-1.sucatalog...
Sep 07 17:27:08 600 products found in http://swscan.apple.com/content/catalogs/others/index-lion-snowleopard-leopard.merged-1.sucatalog
Sep 07 17:27:37 Building index-lion-snowleopard-leopard.merged-1.sucatalog...
Sep 07 17:27:38 448 products found in http://swscan.apple.com/content/catalogs/others/index-mountainlion-lion-snowleopard-leopard.merged-1.sucatalog
Sep 07 17:27:42 Building index-mountainlion-lion-snowleopard-leopard.merged-1.sucatalog...
Sep 07 17:27:43 464 products found in https://swscan.apple.com/content/catalogs/others/index-10.9-mountainlion-lion-snowleopard-leopard.merged-1.sucatalog
Sep 07 17:27:57 Building index-10.9-mountainlion-lion-snowleopard-leopard.merged-1.sucatalog...
Sep 07 17:27:58 repo_sync run ended

Warnings will be normal as some updates will not be available any longer. If the number of products not downloaded is HUGE—say, hundreds of items—then you have a problem. But I think 10 or 20 is normal?

Choose Max Version of OS X You Want Updates For

This is a personal choice based on what Macs you are interested in, how much space you have to dedicate to this, and what Macs you think Apple will remove from the update servers soonest.

You can see all the catalogs in this Reposado file. They are named in a pretty orderly way, so select which OS you want to support and then put in the catalog file for that one and all the versions lower. So if you want to support 10.10 Yosemite and lower, your Preferences.plist would look like this:

AppleCatalogURLs

    http://swscan.apple.com/content/catalogs/index.sucatalog
    http://swscan.apple.com/content/catalogs/index-1.sucatalog
    http://swscan.apple.com/content/catalogs/others/index-leopard.merged-1.sucatalog
    http://swscan.apple.com/content/catalogs/others/index-leopard-snowleopard.merged-1.sucatalog
    http://swscan.apple.com/content/catalogs/others/index-lion-snowleopard-leopard.merged-1.sucatalog
    http://swscan.apple.com/content/catalogs/others/index-mountainlion-lion-snowleopard-leopard.merged-1.sucatalog
    https://swscan.apple.com/content/catalogs/others/index-10.9-mountainlion-lion-snowleopard-leopard.merged-1.sucatalog
    https://swscan.apple.com/content/catalogs/others/index-10.10-10.9-mountainlion-lion-snowleopard-leopard.merged-1.sucatalog

After you add the new catalogs, run sync again:

/Volumes/Data/Virtualization/SUS/reposado/code/repo_sync

Note that supporting up to 10.10 Yosemite takes about 300 GB of space.

Some Final Things

Basically, after you complete the sync, you never need to run Reposado again. The web server and the www folder are all you need. The Software Update server is based on a completely static system, which is super nice and reliable.

If you change the hostname of the server Mac, you can update the Preferences.plist file and then run sync again, and it won’t download any new files, but at the end Reposado will update the catalog files to use your new hostname which is fantastic.

6. Configure the retro Mac to fetch updates from your server Mac

So this is a bit tricky, because it’s likely that your retro Mac(s) have already run all of their software updates. So when you tell them to check for updates from your new Software Update Server Mirror, the retro Mac will still tell you there are no updates available. So how do you test?

If you don’t mind erasing your retro Mac, you could just reinstall the OS.
Install a fresh OS to an external FireWire hard drive and boot from that.
Install an old version of OS X in a virtual machine and try that.

Configure the Retro Mac

All of these have their pros and cons so you decide. But once you get the Mac working and it is ready for software updates, run the following command in the Terminal on the retro Mac:

sudo defaults write /Library/Preferences/com.apple.SoftwareUpdate CatalogURL "http://Server-Bonjour-Name.local/content/catalogs/others/index-lion-snowleopard-leopard.merged-1.sucatalog"

Note that you have to point the OS at the correct catalog given the version of OS X you are running or else it won’t see all of the updates.

Tail the Apache Access Logs on the Server Mac

Tailing these logs will show you that the retro Mac is checking all the updates.

tail -f /var/log/apache2/access_log /var/log/apache2/error_log

Check for Updates on the Retro Mac

Check for updates on your retro Mac and install them. If it’s a fresh install, it may take several reboots to get through all the updates.

Apple Menu→Software Update

What Success Looks Like

In the logs on the server Mac, you should see hundreds of file requests to check for updates. On the retro Mac, in the title of the Software Update window you should see the hostname of your server Mac in parentheses. See the screenshot below.

Some Final Things

In the real software update server, Apache rewrite rules are used so any version can fetch index.sucatalog and the server will smartly rewrite the URL to be the correct one. You can add these if you like, but since you’re probably not running an army of retro Macs, it’s probably easier to just do it on the retro Mac instead. Here are the rewrite rules if you are interested.

RewriteEngine On
RewriteCond %{HTTP_USER_AGENT} Darwin/9
RewriteRule ^/index\.sucatalog$ /index-leopard.merged-1.sucatalog
RewriteCond %{HTTP_USER_AGENT} Darwin/10
RewriteRule ^/index\.sucatalog$ /index-leopard-snowleopard.merged-1.sucatalog
RewriteCond %{HTTP_USER_AGENT} Darwin/11
RewriteRule ^/index\.sucatalog$ /index-lion-snowleopard-leopard.merged-1.sucatalog