Headless Macs and Hamstrung iPads

In the current era of coding agents becoming productivity assistants, iPadOS’ limitations are no longer defined by the lack of desktop-class multitasking or access to external peripherals. A new class of iPadOS shortcomings looms large on the horizon: the iPad’s app sandboxing and the absence of an open filesystem have relegated it to acting as a remote control for agents.

I’ve been ruminating on this thought for some time. I, of course, am very satisfied with the improvements Apple brought to the iPadOS platform throughout the 26 cycle: between new windowing, local capture, a menu bar, and the improved Files app, I can get most of my old-school work done on the iPad Pro without begrudging the experience like I used to a few years ago. What I’ve noticed this year, however, is that iPadOS 26 was an update designed to address the pre-existing low-hanging fruit of quasi-desktop efficiency; by design – and we have Craig Federighi on the record saying as much – it wasn’t intended to reinvent the wheel in any meaningful way.

That would have been fine a few years ago. The problem is that the productivity wheel is literally being reinvented by other companies as we speak. And in an unsurprising turn of events, the Mac is at the forefront of that reinvention, while the iPad is being left behind once again.

I’m writing this as someone who likes to be on the bleeding edge of AI tools. Since the release of Claude Code in early 2025, I (and, realistically, millions of other nerds whose taste aligns with mine) have increasingly moved a lot of my research, automation, coding, and other tasks considered “productivity” to desktop agents. These are powered by the same underlying technology as chatbots, but they’re considerably more powerful: Claude Code and Cowork, Codex, Perplexity’s Personal Computer, and self-hosted agents like OpenClaw and Hermes can understand intent and perform long-running tasks on your computer. They can write code, stay on a task for hours (or even days) at a time, analyze the contents of your screen, and even use a computer on their own. To believe that these AI tools are still a fad and chatbots are useless is misinformation at this point.

As of June 2026, I spend most of my days with two apps constantly open on my M4 Pro MacBook Pro: Codex and Notion. I’m a huge fan of what OpenAI has accomplished with Codex for Mac; their all-in-one package that combines thread-based chats with skills, plugins, connectors, computer use, memories, and system-wide filesystem access has genuinely allowed me to produce content for my audience that I wouldn’t have even dreamed of years ago. Since I started working with Codex, I’ve released a major update to Apple Frames, two CLIs (with two more coming soon), Shortcuts Playground, and a brand new MacStories Shortcuts Archive. These are actual products that are used by thousands of people and are generating real revenue for MacStories. I’ve also created an entire suite of MacStories-only internal apps (now used by our whole team) and am currently in the process of researching my iOS 27 review, creating an app for Shortcuts Playground, and brainstorming a different product altogether for MCP.

I’m doing all of this on a Mac because the true Codex experience isn’t even “desktop-only”: it’s Mac-only.

Let me give you some examples. To make the original version of Shortcuts Playground, I had Codex with Computer Use scrape my entire library on the old MacStories Shortcuts Archive, download over 300 shortcuts, and learn my coding style. Once I had a plugin, I also had Codex create over 1,000 shortcuts on its own, install them in the Shortcuts app for Mac, and debug them visually to find issues. For the new Shortcuts Playground plugin and app, I’m going even further: Codex created over 3,500 shortcuts spanning the entire library of Shortcuts actions while simultaneously coordinating with other Codex threads – some of which are running on my Mac Studio – to build an app, train a local model for Core AI, and constantly iterate on the new harness behind the app. Meanwhile, I’m also spending time in Codex organizing sources for my iOS 27 review, managing my tasks with Reminders and my own RemCTL, and performing general research on any topic I think of. The net result of all this is that I’m shipping more things, making more money for MacStories, saving money thanks to our new internal tools, and – most importantly – learning a lot and having fun.

In all of this, the iPad’s role is to be, once again, an accessory to the Mac – and a rather expensive one at that. I wrote last year about iPadOS’ third-party app problem, and I still think all of it applies today. What’s different in 2026 is that these powerful agentic tools that are redefining coding and knowledge work, and which are centralizing productivity inside so-called “super apps”, aren’t coming to the iPad, but not for political or financial reasons: they’re Mac-only because only macOS is mature and open enough to support them.

In a funny twist of fate, Apple spent years trying to make iPadOS catch up to macOS on the surface, only for macOS’ underlying nature to unlock a new generation of apps that are rewriting the rules of modern software. No amount of windowing and menu bars can change the fact that neither Claude Cowork nor Codex will ever be possible on the current version of iPadOS. From an open filesystem that lets agents poke around anywhere to powerful Accessibility and Screen Recording APIs for developers to features like system-wide hotkeys, dictation, and true background processes, Apple’s oldest operating system is the one that feels the freshest (and the most powerful) in the AI industry today.

Apple’s oldest operating system is the one that feels the freshest (and the most powerful) in the AI industry today.

In fact, the Mac is so powerful and well-equipped for this new wave of desktop agents, it even yields an amazing experience when used in a “headless” setup with no display attached to it. This may have started as a trend because of OpenClaw, but six months later, I believe that a Mac mini with Codex running on it is the best bang for your buck if you’re building an always-on agentic setup based on a frontier model that can do just about anything you throw at it.

Perplexity’s Personal Computer is an alternative to Codex, but it’s less powerful. I hope Anthropic offers something new in this space soon, because Dispatch and Remote Control aren’t cutting it.

Which brings me to the iPad’s only silver lining in this space right now.

Most of my Codex tasks are running on my Mac Studio server, but I also use Codex on my MacBook Pro. Thanks to Codex’s support for remote connections, I can chat with threads running on the Mac Studio from the Codex app on a different machine, which is a fantastic feature. Alternatively, I can use Apple’s excellent (and, again, Mac-only) Screen Sharing app to log into my headless Mac and interact with macOS with superior performance and image quality to VNC. (I also use this HDMI 2.1 dummy plug to unlock 4K resolution when headless.) Coordinating Codex threads across different projects and machines feels like the sort of thing that shouldn’t be possible, yet here we are.

If the iPad is still relevant to me in this specific new way of working, it’s entirely because of the ChatGPT app and the fact that OpenAI cared enough to design a good remote experience for iPhone and iPad users. The Codex section inside ChatGPT is a solid product and getting better every week; it’s also the only app of this kind that lets you connect to multiple computers at once and manage threads across all of them. With Codex remote on iPad, I can continue my projects from the MacBook Pro or Mac Studio, pin specific threads, and keep an eye on all my agents working in the background. In general, it’s also a way to bridge functionalities that are missing from iPadOS. Without Codex remote, I wouldn’t be able to ask my agent to reschedule my reminders and turn some emails into tasks in the same workflow; I wouldn’t be able to tell my agent to go to the Apple Newsroom, find me a specific press release, extract all images from it, and upload them to our CDN.

Perhaps Siri AI will unlock similar capabilities (although I doubt to the degree of a frontier desktop agent), but it’ll still be limited to apps made by companies that decide to support App Intents. When I’m not using my Mac and I think of something I can’t do on the iPad these days, I instantly reach for Codex inside ChatGPT. I suspect this trend will only grow as more AI companies release similar remote experiences for iOS and iPadOS.

Here’s the issue, though: these are remote companion experiences. It’s great that they exist and that OpenAI cared enough to make them great, but they’re still no substitutes for the real Codex experience on a Mac. It’s ironic if you think about it, isn’t it? A headless Mac is still more flexible and powerful than an iPad hamstrung by the closed nature of its own OS and software gatekeeping.

If you’re among the five million people using Codex on a weekly basis and will be planning your next laptop purchase in a few months, perhaps these considerations will change the calculus for you. Especially in the face of price increases and RAM uncertainty, would you be better served by spending $1,499 on a hybrid laptop that gets work done the old way with 256 GB of storage, or $1,499 on a computer where AI is a first-class citizen with 24 GB of RAM and double the storage? If we accept that power users’ priorities and workflows will be dramatically changing in the near future (if they haven’t already!), all prices being equal, which OS is best positioned for the future?

Of course, I like using both an iPad Pro and a Mac for different tasks. But let’s face it; in this day and age – and especially after last week – not everybody has the budget for two computers that have some overlap between them. Sure, I could argue that an iPad Pro + a headless Mac mini is an insane combo to get the best of both worlds these days: the nimble and delightful nature of iPadOS and the freedom to experiment with AI on a Mac. You can install apps like the latest Jump Desktop beta or the great new screen sharing app Mirage on the iPad and use your Mac mini almost as if it were connected to the iPad’s display. Set up Tailscale on your network, and the Mac’s power can be with you at all times. But that’s a lot of money, and a lot of setup, to achieve an approximation of what a single MacBook Air can handle with more memory, more storage, and a couple of Mac apps.

I’m sure that Apple is aware of the changing nature of this landscape, but in a similar vein to chatbots and Siri, perhaps they were unprepared for the tide of agents to accelerate so quickly. If the idea of putting macOS on an iPad Pro continues to be a non-starter at Apple, and assuming agent-based coding and knowledge work are here to stay, what should the company do to make sure the iPad doesn’t get left behind again? Is a sandboxed Terminal for iPad backed by a dedicated “Agent Framework” the solution? Is working with other companies to build more “remote companion” apps the way forward?

Or, perhaps more obviously: how long until Siri AI can also become a capable agent, connected to App Intents, on par with competing frontier agents?

Until, and if, that happens, the iPad will once again play the role of sidekick to macOS.

When it comes to the bleeding edge of AI and pushing the frontier of agents forward, there’s nothing like the Mac.