This is a short follow-up to my Apple Papercuts piece, wherein I bunched together a few more annoyances that I’ve come across while using my iPad Pro extensively on vacation.

If you needed any more proof that Apple doesn’t really do QA testing, I think just two of these would be enough. And I’ve confirmed they are all still there in 26.6.1, freshly released last week.

At first, I thought this was a hardware problem. My brand new iPad Keyboard Cover had been giving me some odd glitches of late (I keep having to physically reconnect it for keypresses to register), but after a few days of using a desktop Bluetooth keyboard I am positive that all the input glitches I’m having are a software problem.

One of the main symptoms is that invoking Spotlight with Cmd+Space works but then typing inside Spotlight fails to register. But a second attempt works, so my attempts at invoking Mail every day have the same outcome:

• First attempt at Cmd+Space, M… does nothing useful–Spotlight appears but doesn’t show “m”
• Hit Cmd+Space, M again–“m” appears and, lo and behold, “Mail (open)” is suggested (after an embarrassingly long pause, but hey, at least it happens)

Yes, I could tap the icon. But if the above doesn’t convince you that nobody at Apple actually tested this, then I don’t know what would. Oh, wait, I have a couple more:

Another interesting bug that has surfaced recently is that nearly every time I use a Bluetooth mouse with my iPad when it’s plugged into an external display, iPadOS swaps the X and Y axes, which is just… ridiculous.

The steps are always the same:

• Wake up the iPad while it’s plugged into an external display (typically by swiping the Home Screen up so that Face ID begrudgingly notices I’m here).
• Turn the mouse on, move it up
• Wonder why the cursor is moving left

You know why that happens? Because my iPad is in landscape mode, not portrait, and when the mouse is detected, iPadOS does not take that into account. But the Home Screen was in landscape mode. I swiped “up”. This is not fucking rocket science, guys.

And, again, for this one there are zero excuses.

Every now and then, while my iPad is plugged into an external display, my entire iPadOS “session” crashes–black screen, emergency spinner on the iPad display, everything gone (well, fake gone, just like the fake iPadOS multitasking).

Over my break, I mostly ran Reeder, Obsidian, Mail.app and Safari, with some cameos by various terminal emulators and the usual social media garbage. None of them are particularly taxing, and the vast majority of my external display time was spent writing or looking up references.

This is not a stability story. It’s not even a reliability story. Having your session wipe out like this is simply unacceptable.

This one’s a twofer: We all know iPad window management is sub-par–it’s not news–but there are two things that annoy me to no end:

• Swiping up on your iPad display to flip through applications completely kills keyboard input on the external screen until you Cmd+Tab back to the application you were typing in
• You cannot even think about picking which windows get assigned to quarter screens.

This last one is tantamount to the Odyssey, and it should probably be on IMAX due solely to its dramatic plot.

After painstakingly inching your mouse towards the almost invisible semaphores, clicking on them to make them actually usable even though they pulse and expand when moused over just to tease you, you then have to play the green button roulette.

That may, according to its internal whims and in a complete travesty of Apple UX polish (that we, the elders, remember from ancient times), either maximise the current window or (maybe) show you a menu.

If you are worthy of the gods (or just plain lucky), you will finally get a window layout menu and get to pick “Fill and Arrange”, which has completely random behaviour, making it impossible to figure out where your windows will end up, and leading you to believe you have any choice in the matter when you later try to arrange them manually.

And no, you can’t have a right-first half-screen arrangement, either. You are not that worthy.

I’ve spent the better part of six months building piclaw–my personal AI assistant, workspace and, occasionally, agent swarm–on top of Mario Zechner’s pi engine, and I think it’s time to write about not just my motivation but also how I feel about having invested that much time into the whole thing.

This is important (at least to me) because pi is an excellent coding agent with a very clear point of view about how things should work. The internals are concise, well structured and easy to follow, with the brilliant twist that extensions can literally take over the entire thing–to the point where you can pretty much rewrite the entire agent loop (however you care to define loop these days).

Building a different kind of UI on top of it has been educational, very rewarding and occasionally maddening, and I’ve reached the point where I need to write down what I’ve learned and a lot of the underlying rationale–partly because I just want to use the thing now and move on, and partly because there’s a lot buried in the project documentation itself (there are a lot of whats and hows, but relatively few whys).

The key thing that captivated me is that pi is, in effect, a self-modifying agent harness.

Yes, self-modifying. Like… a virus. I like to think that its virality (however you cast it) is one of the unstated reasons it has found its way into a lot of projects lately, but let’s skip that bit and just reframe “self-modifying” as both self-improving and self-evolving without dipping too much into the penny arcade theatrics of AGI.

I’ve come to the point where I think that even without agency, self-modifying harnesses like pi are way more powerful than just about anything we’re getting from megacorps, because they can morph into your own completely personalised environment–which is what piclaw became for me.

When I started out fooling around with what eventually became steward, the field of open coding agents was a mess of half-finished Python scripts and VS Code forks, and pi stood out because it was opinionated in the right ways: TypeScript as the runtime, a clean turn-based conversation model, good terminal UX and–critically–a willingness to evolve quickly. Mario Zechner made strong choices about tool calling, context management and model interaction, and they were essentially the right ones.

And if you take the essential bit literally, the thing pi got most right was restraint. Or, if you have been following the philosophical debate about AI use, taste.

At the risk of reiterating the basics most people already know about pi, it starts with a small, carefully chosen set of built-in tools–file I/O, shell, search and editing–and leaves the LLM to fend for itself in UNIX land, which gives it tremendous power and flexibility.

Compare that with what AI lab harnesses are becoming: sprawling collections of specialised tools, bespoke UI panels, inline diffs, notebook integrations, code review modes and whatever else someone thought of that quarter week. Every one of those features eats context, adds latency and makes prompts longer–which means the model has less room to think about your actual problem.

pi starts from the other end: give the model the minimum surface it needs to be effective and spend the rest of the token budget on the actual problems at hand. The introspection is excellent too–you can see what the model is doing, which tools it is calling and what the context looks like at any point. No magic, no hidden system prompts, no mystery. That transparency is worth more to me than feature polish, because it means I can debug things when they go wrong.

I didn’t necessarily want just a coding agent, though, and after a while, I realised I didn’t even want to run it in a terminal. I wanted an extensible agent that could run headless, manage my homelab, edit my wiki, file links, take notes, run scheduled tasks, and generally be useful in ways that might only occasionally have to do with writing code.

pi’s small tool surface and clean turn model were close enough to what I needed that building on top of it seemed faster than starting from scratch.

As I’ve written many times before, I don’t run coding agents locally–that’s why I spent quite some time coming up with things like agentbox and webterm to run them in remote machines.

But the biggest departure from pi came from using it inside vibes, which started out as a generic web UI that I could use from my phone. And with my mobile background, it was pretty obvious (at least to me) that a highly optimised web UI was vastly better than using WhatsApp or Telegram as a bridge–not only could I make it much more secure over Tailscale (without any middlemen), but I could build a much nicer, continuous experience across devices, reconnecting from anywhere and picking up exactly where you left off:

Another key factor is that I almost invariably begin and end my days on an iPad, which pretty much defined the rest of the UX–I can reference timeline messages, annotate them with Apple Pencil, etc., making for somewhat terse but very effective interactions, especially when doing reviews. I just toggle between Safari tabs to move between chat and GitHub or Gitea diffs, and with a little bit of AGENTS.md tweaking or per-session prompting things can be very productive.

The entire thing unfolds like origami–files on one side, plan trackers on the other, documents opening into tabs or detached panes, and ample touch support throughout (resizing panes, swiping between chats, etc.). I also took advantage of pi’s brilliant session tree internals to create multiple “agents” (that can talk to each other inside each instance using a chat tool, and even across instances…)

• Several agents that I can switch quickly between (in this case they’re actually coordinating to fix an add-on and deploy it across the “fleet”)
• A timeline with rich link previews, my latest prompt, and three temporary panes:
  • Thinking output from the model
  • Tool output
  • Tool execution details (what, current working directory, and git branch)
• A plan sidebar that the model started using without prompting (this is gpt-5.6-sol, so it tends to remember previous instructions)
• A compose box with model status/plan/context information (you can’t see the submission, previous message references and image attachment widgetry in this shot)

The top dashboard and the side pane are add-ons, and they’re designed to be used on demand, so the typical UX is much less cluttered–but my key point is that despite several attempts we’ve made at “improving” it, this has been working out really well for me on the iPad with both voice and Apple Pencil input, and I seldom use anything else these days.

One thing you can’t see is that it is running on a remote VM–piclaw has a handy little widget I can pop up on the top right-hand side that gives me sandbox instance info:

• Constantly switching between devices (iPad, work laptop, iPhone, work AVD, MacBook, Linux laptop, etc.)
• Multiple concurrent sessions (typically one per project) in each instance.
• Very long sessions that can last weeks.

Unlike people who have the luxury of uninterrupted focus time and can work on only one thing at once, I have to switch constantly between meetings, coding, planning, researching, writing, etc. I tend to work on some things in very short bursts over quite long periods of time–and having something stuck in a terminal someplace, even over tmux and ssh, would never cut it.

This is probably the biggest reason why I’ve never considered piclaw a “product”, even though it naturally evolved many of the trappings of other coding agents–including external add-ons.

But the key thing is that all the above are just extensions, since I leaned hard on pi’s extension mechanism, extending it to support the web interface.

pi has a very capable terminal UI, and its extension contract exposes a bunch of it, but a lot of its flexibility doesn’t (or didn’t) cross the IPC interface, so I gave piclaw its own browser UI contract: extensions are route- and event-aware, and the shell extension host can mount, focus, resize, save, detach or dispose of them.

They retain the standard pi extension features, but can provide editors, file viewers, terminals and even a VNC client without reaching into the main application bundle. And, of course, they can do all sorts of fancy widgetry in the timeline (which has used SQLite from the start and can serialise widget states).

There are many things that are just intrinsic to piclaw, of course. The piclaw web server provides a bunch of scaffolding for managing UI panes, SSE events, settings, the works, plus there is an encrypted keychain, database and state introspection for the chat/sessions and file attachments in the timeline, etc.

But most of the shipping extensions started out like this:

{
  "piclaw": {
    "compatibleVersions": ">=1.8.0",
    "tags": ["example"]
  },
  "pi": {
    "extensions": ["index.ts"],
    "web": {
      "entries": ["web/index.ts"]
    }
  }
}

This translates into actual code like so:

// index.ts -- a normal Pi extension, loaded by the agent runtime
// schema and handlers omitted
export default function example(pi: ExtensionAPI) {
  pi.registerTool({ name: "example", parameters, execute });
  pi.on("session_shutdown", closeResources);
}

// web/index.ts -- loaded separately by Piclaw in the browser
__piclaw_web.registerPane({
  id: "example-viewer",
  label: "Example",
  capabilities: ["preview"],
  placement: "tabs",
  canHandle: ({ path }) => path?.endsWith(".example") ? 100 : false,
  mount(container, context) {
    return createExamplePane(container, context);
  }
});

Slowly, gradually, piclaw effectively built its own UX out of what are essentially all pi extensions, which I think is a great example of how good the original design was.

Now, the design still is good, but the problem with building on top of someone else’s opinionated engine is that, to an outside observer, their opinions keep changing. pi is very actively developed–which is good–but there was a period when every upstream bump brought a non-trivial risk of things breaking in ways that were hard to diagnose.

I am very happy with piclaw as a tool to the point where I seldom use anything else, but I want to truly use it rather than spend so much time maintaining it, and over six months I’ve dealt with:

• Tool-calling interfaces changing shape
• Context-window management behaving differently after upstream refactors, causing my longer system prompts to be silently truncated.
• The model configuration layer being restructured, each time requiring changes to my settings and onboarding code.
• Streaming behaviour changing subtly enough that my web UI’s SSE handling would occasionally drop tokens or duplicate thinking indicators.

A later refactor to model handling fortunately converged with my approach, but still required a day of coddling GPT-5.6–very soon after I had spent two days integrating and testing a new context-compaction approach.

In a way, all of the above was useful because piclaw now has a gazillion regression tests–not just for the core and event loop (since my event loop has to do a fair bit more than “just” running a TUI, like routing SSE events, updating tables, etc.) but also for the UX (including a very spiffy PDF report that spans dozens of Playwright tests).

So the first “new” thing I learned out of the whole thing was how to apply the TDD mantra I had to follow in a few customer projects to piclaw, including getting the LLMs to generate decent user stories (and Gherkin) for tests and making sure the entire thing can run in Actions. I’d done it before, but not at this scale and depth for a single project.

This makes builds slow, but it’s completely consistent with my usual process of ensuring LLMs generate useful code, and it’s been pretty rewarding.

The flip side is that spending three and a half evenings on compatibility work when upstream broke stuff I didn’t expect sucked. However, I don’t blame Mario for this. It had to happen.

The core of pi has got to be a very hard thing to reshape and evolve (especially considering the explosive popularity it’s been enjoying), and the constant model and provider churn certainly doesn’t help. If you peek under the hood, the sheer amount of work poured into pi-ai just to talk to provider endpoints is batshit insane, and is possibly tracking more moving targets than NORAD.

Since I first dated this draft on June 19th, piclaw has gone through sixteen distinct Earendil releases, from 0.79.8 to 0.84.1. Most were uneventful dependency bumps, but package/API splits and a ModelRuntime rewrite for provider discovery, credentials and model catalogues prompted another couple of late evenings, since I now rely upon the latter for my own carefully crafted Azure and GitHub extensions (because, well, I need to dynamically resolve models that are not public).

I could just let upstream stabilise, sure, but the way things are going I’m pretty sure that will take years, and none of the above requires pi to promise API stability. But since just using the SDK and IPC isn’t really an option for me (at least not yet–more on that in a bit), I have to accept these as the natural consequences of shaping my working environment on top of a moving foundation–Earendil has more on their plate than catering to my somewhat eccentric use case.

Compaction pushed this furthest, since my style of work lends itself to very long sessions and I have access to multi-million token models, so my usage pattern seems to be very different than most.

Upstream added reasons, retry metadata, post-compaction estimates and eventually retry lifecycle events; my smart-compaction add-on grew summary validation, continuity checks, provider-specific execution and request-auth preservation around those hooks. When I implemented provider-native remote compaction, I then had to handle summaries that one provider could create but could not replay through another, etc. That made me respect the work done in pi-ai even more, by the way…

Fortunately, more recent upstream work has converged with decisions I had already made. Cache-friendly dynamic tool loading, full provider extensions, and compaction metadata plus retries for failed summaries are all things a long-running assistant needs, and let me ditch some of my workarounds. I still had to adapt piclaw’s credential store, model refresh, scheduler and extension loader, but I was no longer maintaining those ideas entirely outside the engine, and some of that scaffolding became integration code.

And I’ve finally caught up to the point where I am now proactively tracking the new upstream agent harness and started breaking down piclaw into individually testable “effectors” (for lack of a better word) that can just plug in to the new agent loop as it changes state.

With luck, I should be able to adopt the new harness as it comes out. Worst case scenario, I’ll have to refactor a bit more, but some of it is long overdue, to be honest.

But let’s take a little detour.

The other thing I’ve learned–and this is less about pi specifically than the TypeScript ecosystem in general–is that the runtime overhead is brutal on constrained devices. Bun is, to me, a massive improvement over Node.js (and its recent upgrade to 1.4 is one of the reasons I decided to finally clean up my notes and post this), but it still has its challenges.

Using Bun 1.3, piclaw running on my ARM devices used somewhere between 400 and 600MB for the main process, depending on how many tools are loaded and how much conversation state is in memory. On a desktop or a VM that’s nothing, but on a smaller ARM board that is also trying to run builds, it is a meaningful chunk of RAM.

Early results with 1.4 (very early, since I just did the first piclaw release based on it) are… mixed. I have seen some of my instances go down to 200MB RSS, but others remain in the same range.

Bun is fast, and I genuinely like working in TypeScript for the web UI and tool surface (mostly linting and testing, honestly, because I still don’t really like the language). But the combination of JavaScript runtime overhead, the node_modules graph and a process that loads dozens of tool definitions at startup means I am paying a tax that a compiled language would avoid, and I am constantly reminded of that.

I still prefer Python (and continue to explore doing harnesses in it), so there’s a draw away from the internals of pi that I just cannot ignore.

Anyway, I adopted a few different tactics to try to keep things under control.

The first mitigation was architectural, suitably pi-aligned, and typically lazy: I split piclaw into a core runtime and a set of lazy-loaded (ha!) extensions, hacking session management (which I also extended to support multiple parallel running sessions) to support dynamic loading.

So extensions like Proxmox tooling, Portainer integration, SSH, wiki helpers and other (incidentally) context-heavy tools are loaded only when the model needs them, rather than inflating the base process (or the session) from the start.

This helped, and eventually converged with pi’s recent releases, which made this less of a hack as the core added its own dynamic tool loading (which was tricky for a bit since it mangled the cached prompt prefix in my custom handling…). I only use subprocesses for scheduled tasks and some add-ons, but I wired those through as well.

The thing is, shipping all those extensions with piclaw itself started becoming unmanageable, so…

I eventually decided to move the larger integrations into a separate piclaw-addons repository, making it possible to download and install things directly from it:

This created more maintenance, but it also forced me to treat extensions differently in general. The repository now has standalone-import tests, metadata validation, etc., and one of my slow burning tasks has been migrating stuff out of the core repository into what is now a nearly 50-strong add-on library.

That includes niche provider integrations, infrastructure clients, viewers and editors, delegation and compaction machinery, terminal renderers and small pieces of UI that make sense only in the web app. Each is installed as a Pi package and its runtime entry still receives pi’s native ExtensionAPI, so tools, events, session state and shutdown semantics still belong to the core (which is why I’m quite optimistic about my chances of adopting its upcoming pi harness without a lot of breakage).

Also, some of the best improvements to my workflow came via contributed add-ons: delegate, in particular (which just invokes pi as one or more subprocesses, at least until I find the time to refactor it), has been pretty useful for things like “audit this PR independently using sol, terra and opus and give me an assessment”.

Oh, yes, and that scary thing around the add-ons library above is the Settings pane. Every extension in piclaw (bundled or add-on) has access to a settings contract that lets it create and render its own UX. Here’s the scheduled tasks pane, for instance.

Settings panes use a fairly straightforward pattern: the browser talks to an authenticated /agent/addons/api/<addon>/<action> endpoint, the runtime registers the handler, non-secret values go into the extension KV store and passwords or tokens go into the keychain.

But there’s more to this than just the (slightly overkill) amount of functionality I built into piclaw. Using it has also forced me to reflect (and learn) a lot about how to effectively use LLMs across the board.

One of the things that became obvious after keeping sessions around for weeks is that the conversation itself is mostly disposable–but only just. The most useful bits are what survives outside it–files in the workspace, instructions in AGENTS.md, and skills.

Like everyone else, I leverage agent skills extensively, and have dozens of SKILL.md files and scripts that describe how I want recurring jobs done (including all the little caveats I would otherwise have to rediscover every few months).

That is a much saner kind of memory than stuffing old chats into a vector database and hoping similarity search will do the right thing, but I’ve found there are multiple complementary aspects of agent memory and ways to ensure reproducible behaviour.

To begin with, each new session gets the same workspace and operating conventions, plus enough current project state to resume work without dragging months of conversational debris into the context window.

But I’ve also incorporated a recurring self-diagnosis that does light tweaks to skills and a small set of “memory” files. Every night, an out-of-band “dreaming” session goes over recent activity, updates human-readable daily notes and distils the useful bits into preferences, corrections, project state and a compact startup index–while pruning things that no longer need to be folded into every session. It is deliberately lossy, and all the better for it.

Then there is late-night-regrets, my somewhat pointed name for an add-on that looks back at interaction history and classifies course corrections, misinterpretations, over-engineering, under-delivery, context failures and useful proactive work. Typically for me (if you’ve ever come across any of my news processing pipelines), the classifier is a small Bayesian affair that consumes no model tokens; a separate reflection pass rates high-confidence failures and turns them into notes or steering cues for later sessions in a feedback.md file that is referenced when starting a new session.

That is about as much “self-improvement” as I am willing to trust right now: review what happened, summarize what went wrong, and keep changes to a (very) limited set of files. There is no model secretly rewriting AGENTS.md at 2:30 in the morning–it just wakes up with better notes and, occasionally, a list of regrets.

But me being me, I had to take it a step further.

Memento came out of wanting to carry some of that knowledge across machines and agents without sharing chats, credentials or piles of machine-local cruft. The durable concepts are Markdown in Git, split into namespaces and put through a proposal/curation flow, and I initially designed it to share skills and their associated scripts and assets. I hacked in my own embedding engine, but as usual with me it relies mostly on indexing rather than taking embeddings as the source of truth–which, given my experience with opaque memory systems, is an important distinction.

This is only a month or so old, but has already proven itself useful in very mundane ways, like allowing piclaw to replicate itself to new machines and bootstrap them with the shared skills available to every instance:

The best thing? Memento works very well with other agent harnesses, including OpenMinis on my iPad.

piclaw is still my primary assistant, running on six machines and doing useful work every day. The extension architecture made it maintainable, and pi’s upstream improvements continue to make it better.

But, again, it is a “product” for one. And it is quite likely to stay that way, but part of the reason for that is that I very strongly believe that this kind of thing is already a commodity and that it makes zero sense for anyone to invest on selling AI code editors, shells, etc. Partly because the people who can build these things are increasingly likely to do it for themselves, and partly because the least common denominator is already out there in a zillion form factors.

Regardless of everything I’ve learned in the process, the most interesting part (for me, at least) is that pi’s philosophy is the key differentiator–having a self-modifying agent hardness to build from is what enabled me to very quickly build piclaw up from a web wrapper into my main working environment, with its own interface, extension model and accumulated habits, and I’m going to keep following that approach going forward.

Here’s to the next version–but first, I need to enjoy my last couple of vacation days.

I am most definitely not the first person to mention this, but the past year has seen a Cambrian explosion of two things: AI deniers who base their judgement on very limited exposure (or effort to use it) and thousands of variations on software of all kinds, from the perennial to-do list to AI-infused toothpicks.

Which, let’s face it, is a bit much. It’s bad enough to go on social media and be pitched things I don’t need, but the hypefest around new startups hawking their wares to fill hitherto undiscovered “problems” in increasingly pointless sub-niches is a bit much too. I find the entrepreneurial energy heartening, but most of them solve no real problems whatsoever.

I mean, how many code editors can you have anyway? And workflow engines? And CRM pipelines? There is a dizzying amount of almost-identical AI-driven solutions out there trying to land the ideal five-word VC catchphrase, and it’s just tiresome at this point.

Plus if you take the long view, most of them are completely divorced from the realities of, say, traditional IT, which has turned into an ouroboros of complexity thanks to geological eras of non-technical decision-makers – but that’s beside the point right now.

The one thing that I find positive among all this (and that I’ve hinted at a few times in the past) is that anyone with a systematic take on things can now create whatever tools they might need to scratch their particular itch(es) – the results may not be perfect, and they may have an audience of one, but they can unblock time, patience and capabilities they would otherwise lack and improve things in general for themselves, without having to conform to someone’s idea of a “product” or jumping through hoops to make their workflows fit a tool.

Of course, the flip side is that it is all too easy to go overboard (when you have AI, everything looks like a solvable problem), so restraint and taste – which is probably the most effective, even if somewhat passive-aggressive and snobbish criticism you can lob at people these days – are essential.

But this ability for people to design tailored solutions for themselves is, I think, what SaaS vendors (and system integrators) fear the most. In an age where anyone can point an LLM at a bunch of APIs and say “build me a CRM that works for me” (which is something I’ve seen done, to the horror of a friend of mine working at Salesforce), the “value” of customisations has to be replaced by something, and believe me, it’s not going to be a consulting firm’s business acumen – or even their taste (which is nearly always lacking).

That does not make the tools magical, of course – they still need proper boundaries, mature tooling and someone who understands the result.

But on a smaller, personal scale, it’s kind of ironic to think that probably the main reason this is going to kill the appeal of most SaaS is that we’ve spent a couple of decades killing native desktop development in favour of kludgy, half-baked web UIs that are all variations on lists of things people click on.

And believe me, if there is one thing that LLMs can do perfectly, it’s web interfaces with lists of things people click on.

Since I got a new printer last week and I’ve been documenting my endeavours in this realm in a rather haphazard way, I thought it would be useful to do a sort of catch-up/snapshot of where things are (and have been) for a while now.

Read More...

Yesterday morning I switched this site to its fourth major engine, a little over twenty years after sketching out the core idea behind it. The new generator is called sashimi, is written in Go, and runs almost entirely inside GitHub Actions–which is mildly amusing because the first Sashimi, in 2006, was also meant to batch-render this same filesystem tree using dependency tracking.

Read More...