Overview

May 2026 was an exceptionally prolific month — sixty posts that reveal a writer fully immersed in the collision of Apple’s software ambitions, AI-assisted app building, and the evolving character of the open web. The dominant thread is a hands-on technical journey: building a custom task manager from scratch using Codex and Claude Code, abandoning Things 3, and connecting it all with n8n automation. Apple commanded substantial attention, spread across hardware anxieties (Mac mini price hikes, RAM shortages), iOS 26/27 software previews, and pointed critiques of App Store dynamics. Underneath it all runs a persistent philosophical current — questions about AI-augmented writing, the open web’s future, and what it means to be genuinely productive in 2026.

1. 🤖 AI-Assisted Development & Claude Code

The month opened a fascinating introspective loop: what does it mean to rely on AI tools, and when does assistance tip into dependency? Several posts document the friction of working with Claude Code for browser-based development — Can’t Make It Work captures an honest failure mode, finding that Claude Code’s local browser integration wasn’t cooperating, while OpenAI’s Codex handled the task with less ceremony. Yet the author immediately follows up with I’m a Loyal Guy, acknowledging a gravitational pull back to the Claude ecosystem despite the detour.

Beyond the coding frustrations, Claude became a creative instrument. Playing With The Digital World and I Love Dashboards describe using Claude’s Live Artifacts feature to generate visual timelines and interactive dashboards from Craft Daily Notes data — a genuinely novel use of AI not as a code generator but as a data visualisation partner. AI-Powered Title Suggestions marks a milestone: Anthropic’s API is now embedded directly into the Micro.blog editor, surfacing title suggestions automatically. This drew a thoughtful follow-up in When Does Using Tools Become Laziness?, which reframes AI title assistance as a legitimate aid for non-native English writers rather than a shortcut.

Seizing Triggers to Reconsider introduces a subtle systems-thinking angle — token limit exhaustion isn’t just a billing event, it’s a signal to reconsider scope and approach. And Under the Hood closes the section on a reflective note: building automation workflows from scratch with Claude AI and MCP support deepens comprehension in ways that pre-built solutions never could.

Key themes: Claude Code, Codex, Live Artifacts, Anthropic API, AI title generation, MCP automation

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2. 🌐 Web Apps & Personal Projects

If there is a single narrative arc to May 2026, it is this: the complete migration from Things 3 to a custom-built task manager web application. Burning Tokens kicks off the story mid-development — Codex is proving itself capable, but noticeably hungrier for tokens than Claude Code, a tradeoff the author tracks carefully. By Making Progress, the application has reached 70% completion, with Codex’s in-browser testing loop proving superior to Claude Code’s workflow for this particular project.

The database layer gets its own chapter. Switching DB Backend Easily documents a pivot from Airtable to PostgreSQL via Neon, driven by API rate limitations — a mature engineering decision made mid-build without drama. Daydreaming All The Time is the most unexpectedly philosophical entry: migrating tasks out of Things 3 revealed that a large portion of the backlog were aspirational fantasies rather than real commitments. The migration itself became a moment of personal clarity.

I’m Done With Things marks the finish line after four intensive days — a fully operational custom task manager, built with Codex and Claude Code, replacing a commercial app entirely. The coda arrives in Archiving Micro.blog Bookmarks, where an n8n workflow connects the Micro.blog bookmarks feed directly into the new bookmark manager app, demonstrating that the custom-built ecosystem is already absorbing real workflows.

Key themes: OpenAI Codex, task manager, Postgres, Neon, Airtable migration, n8n integration

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3. 🍎 Apple: Products & Hardware

Apple’s hardware story in May was largely one of quiet deterioration — pricing up, configurations down, and speculative futures dangled. Apple Mac Mini Storage Changes and On Mac SKUs Optimization together tell a familiar tale: the 256GB base model disappears, prices climb to $799, and RAM configurations vanish from Mac mini and Mac Studio alike, attributed to memory supply constraints. The author’s analysis is pointed without being alarmist.

In contrast, the speculative posts carry genuine enthusiasm. AirPods Ultra? makes a compelling social-acceptability argument for AI-enhanced earbuds over pendant-style AR accessories — wearables that disappear into everyday life rather than announce themselves. Apple Watch Face Store? frames the absence of a curated watch face marketplace as a missed revenue opportunity, while Apple, Copy This! singles out the Bauhaus Clock app as the design standard Apple should be aspiring to.

On Apple’s Next Disruption closes the hardware section on an ambitious note — drawing a parallel between the iPhone’s transformation of mobile carriers and a potential Apple move into prescription eyewear. The historical analogy lands with weight.

Key themes: Mac mini pricing, Mac Studio RAM, AirPods Ultra, Apple Watch faces, wearables, prescription eyewear

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4. 📱 Apple: Software, AI & iOS 26/27

The software front was dominated by the iOS 26/27 transition — a period of current frustration and future anticipation existing in uncomfortable tension. Enjoying Stable Apple OSes? opens the section with a sharp observation: the pre-WWDC window that should deliver stability is instead riddled with unresolved bugs. iOS 26.6 Betas: No Thank You escalates this into an explicit request — skip the interim release entirely and focus energy on iOS 27.

The iOS 27 previews generated genuine excitement, particularly around AI integration. Shortcuts AI — enthusiasm for natural-language shortcut creation — stands in direct contrast to Cancelling Apple Shortcuts, where abandoning the existing Shortcuts ecosystem entirely in favour of Claude AI alternatives felt like the obvious move. The cognitive dissonance is acknowledged and left productively unresolved. On Apple AI Chat Beta and Bye Bye Grammarly? both point toward a future where Apple’s native AI capabilities — auto-deleting chat history, system-wide grammar tools — make third-party alternatives redundant.

Really? provides the comic relief: iOS 26’s Liquid Glass design receiving an Art Directors Club Gold Cube award prompts barely-contained skepticism. Is Apple Really Working on iOS 28? closes the section with a management-capacity question worth taking seriously — can Apple’s engineering teams simultaneously ship quality iOS 27 improvements and begin iOS 28 development?

Key themes: iOS 26 bugs, iOS 27 features, Shortcuts AI, Apple AI Chat, Liquid Glass design, Grammarly replacement

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5. 🏛️ Apple: Business & App Store

The App Store came under sustained critical pressure in May, with Manton Reece’s Inkwell app serving as the month’s recurring exhibit. Come On Apple, Take It! and The Irony of the App Store together document Inkwell’s repeated rejections — an open-web-derived app that should epitomise the kind of software Apple claims to champion, blocked by a review process that prioritises form over substance.

The End of the App Store as We Know It? widens the lens considerably: if AI can generate functional applications on demand, the entire static-software review model becomes structurally obsolete. Who Wants To Pay Fees in a Commodity Market? examines developer reluctance to commit to Apple’s potential Siri integration commission structure — a tension that becomes acute when the underlying AI capabilities are increasingly commoditised.

You Know Apple Created Chaos When… notes the absurdity of Apple needing to publish documentation clarifying that its own Creator Studio apps aren’t third-party imposters. So Many Questions, Still So Few Answers probes the Private Cloud Compute capacity allocation question, while Melius’ Ben Reitzes Raises Price Target on Apple to $385 frames agentic Siri as a potential $65 billion revenue opportunity by 2030. Still Looking for the Killer App provides the necessary counter-weight: ordinary iPhone users remain unconvinced that iOS 27 AI features justify an upgrade.

Key themes: App Store reform, Inkwell rejections, agentic Siri, developer fees, AI app generation, Apple stock valuation

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6. ✍️ Blogging, Writing & Open Web

May delivered a cluster of posts examining the act of blogging itself — its mechanics, pressures, and philosophical underpinnings. Give It a Title or Not? and On Micro.blog’s Blog Post Title Handling tackle a deceptively technical question: do short posts require titles, and how does Micro.blog handle the downstream cross-posting consequences? The answer turns out to have real implications for how content surfaces on Bluesky and Mastodon.

Where Is the Right Balance? confronts the newsletter publication anxiety directly — the internal pressure of maintaining high output pace against the sustainability of doing so. An Update About Me is a quieter moment: revisions to the Who Is Numeric Citizen page, with a notable aside about AI-driven impersonation risks making personal accuracy feel newly urgent.

The open-web dimension grows sharper across several posts. Open Web + People = ? uses Reddit’s mobile web blocking as a lens on how human participation makes platforms — and how platforms repay that participation with walled gardens. Internet in 2026: Closed Platforms extends this frustration to YouTube’s API limitations and Google Cloud’s setup complexity. Now That Google Broke Its Promise to the Web lands the most significant argument: Google has violated the implicit grand bargain of the internet by training AI on creator content without returning commensurate traffic.

Where Life & Tech Collide is the month’s most personal post — a bike accident involving the author’s wife, and how iPhone emergency features and Apple Watch SOS notification enabled timely help. Food for Thought on a Rainy Friday is speculative and philosophical: would permanent content embedding change how people share on the open web? Disconnecting for a Short While offers a brief, grounded coda — a 50 km bicycle excursion around Montreal Island, cool temperatures and scattered showers notwithstanding.

Key themes: Micro.blog cross-posting, newsletter pace, open web, Google’s grand bargain, personal identity, Montreal

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7. 🔍 LLMs: Observations & Critical Perspectives

May’s LLM commentary was focused and incisive, if compact. CIOs Ready for Another Role-Change as AI Becomes Agent of Chaos sets the tone: as AI systems become autonomous agents, CIO responsibilities shift from system-building to outcome-governing — a structural change with no clear playbook.

I Want To Believe But… No, I Can’t. is pointed skepticism about Meta’s claims regarding truly private incognito chat in their AI application. The author’s doubts are framed with a mix of amusement and genuine concern. My First ChatGPT Ads! documents the unsurprising but still jarring experience of advertising appearing within the free ChatGPT tier — with a practical sidebar about blocking hostile countries via DNS. AI Data Centers Are Deeply Unpopular, Across the Political Spectrum cites Gallup data to make the case that the AI industry’s infrastructure build-out has become a public-relations liability, as data centres increasingly prioritise AI workloads over other tenants.

Key themes: AI governance, Meta AI privacy, ChatGPT monetisation, data centre backlash, LLM infrastructure

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8. 🛠️ Tools, Apps & New Discoveries

The tools section is anchored by three weeks of Rodecaster Video S coverage — a hardware deep-dive that reads as both review and reality check. Rodecaster Video S Model Review opens with cautious optimism about a more affordable video production path. Read The Fuckin Manual! delivers first-contact honesty: the device has a genuine learning curve, and the documentation for a complete production setup doesn’t yet exist. The RODECaster Video: A Downgrade? completes the arc by cataloguing real trade-offs — most critically, the loss of 4K recording capability versus Mac-only production.

Feeling Tired of Apple Keynote? branches into presentation design, exploring Canva and Acorn as alternatives for YouTube thumbnail creation. Test Micro.blog Native App is a brief but positive note on the Mac app’s improving trajectory despite its still-minimal footprint. Other Browsers Keep Disappointing Me runs Dia and Zen through their paces against Safari and Arc, concluding that Apple’s browser continues to hold its own through sheer integration depth.

Doctors Surprising Practice: Texting X-Rays Using WhatsApp is the month’s most unexpected discovery — hospital staff routing X-ray images through WhatsApp Web and Windows screenshot utilities because the official software simply doesn’t support the workflow. It’s a micro-documentary of how real people actually use technology when institutional tools fail them. WordPress 7 shipped with new AI features, where are they hiding? lands a similarly practical frustration: advertised AI capabilities that remain invisible after a clean installation. My Reading Workflow Revealed closes the section with a detailed map of the author’s content consumption architecture, centred on Inkwell with multiple input tiers.

Key themes: Rodecaster Video S, browser alternatives, Micro.blog Mac app, WhatsApp in healthcare, WordPress 7 AI, reading workflow

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Mentioned Apps, Products & Services

AI & Automation: Claude Code, OpenAI Codex, Claude AI, Anthropic API, ChatGPT, Meta AI, n8n

Development & Hosting: Neon (PostgreSQL), Airtable, Vercel, WordPress 7, GitHub

Content & Publishing: Micro.blog, Ghost, Inkwell, Bluesky, Mastodon, Reddit

Productivity & Utilities: Things 3, Apple Shortcuts, Craft, Grammarly

Developer Tools: MCP, Claude Live Artifacts, Anthropic API

Social & Communication: WhatsApp, WhatsApp Web

Apple Products & Platforms: Mac mini, Mac Studio, AirPods Ultra, Apple Watch, iPhone, iOS 26, iOS 27, Liquid Glass, Siri, Private Cloud Compute, Apple Creator Studio, Apple Keynote

Other: Rodecaster Video S, Bauhaus Clock, Dia browser, Zen browser, Safari, Arc, Canva, Acorn

Digest covers 60 posts published in May 2026 · Generated June 2, 2026