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A 1973 transcript published as an RFC by Vint Cerf documents a conversation between two early AI chatbots: PARRY, designed to simulate paranoid schizophrenia, and ELIZA (DOCTOR). The exchange shows them discussing topics like bookies and racketeers, offering a humorous look at early chatbot interactions.

macOS Tahoe enforces "squircle jail"—rounded-square app icons—on Mac App Store apps, but developers distributing outside the store can use the NSDockTilePlugIn API to display custom icons that persist after quitting. Iris is one example of an app offering alternative icons this way.

A Kickstarter campaign for 'Searching for SmarterChild', a documentary about the AOL Instant Messenger chatbot that once had 30 million users, is in its final week and still short of its funding goal.

The article argues that Claude for Mac is an Electron app because its lead developer, Felix Rieseberg, is a former Microsoft engineer known for porting Slack to Electron and has a professional history strongly tied to the Electron framework.

Fantastical 4.1.15 introduces Calendar Mirroring, a privacy-focused feature that lets users connect two separate calendars so events from one automatically appear on another, with the option to show full details or just mark time as "Busy." All event data stays on the device and is not sent to Flexibits servers.

Revisiting his 2018 piece, John Gruber says his concern about Electron harming native Mac apps was justified, but native Mac apps are now resurgent. He critiques Anthropic's Claude as an "Electron turd," noting the irony that Claude itself can generate quality native Mac code.

Day One, the journaling app for Mac and iOS, has introduced Daily Chat, a guided reflection feature that uses AI to help users talk through their day and shape their thoughts into a journal entry. The feature is designed to assist those who struggle with how to start writing.

After 28 years, longtime columnist Jason Snell published his final column at Macworld. He reflects on starting at the publication in 1997, when Apple was near bankruptcy, Steve Jobs had just returned, and the company's survival was uncertain. Snell had been transferred to Macworld after his former magazine, MacUser, folded.

Maestral, the open-source Mac Dropbox client known for its simple and lightweight syncing, has been retired. Developer Sam Schott archived the project in July 2026, citing lack of time and no longer using Dropbox himself. The current version will continue working for now but will not receive further updates or maintenance.

John Gruber links to an Accidental Tech Podcast members-only special where the hosts explain what makes a "Mac-assed Mac app" and discuss why both users and developers should care about such apps. ATP memberships are $8/month or $88/year.

John Gruber reflects on Allen Pike's argument that ChatGPT's Mac app excels with live document attachments — a native feature iOS can't replicate. He notes Anthropic's chief product officer Mike Krieger moved to head an internal lab team rather than focus on polished desktop tools.

Backblaze has stopped backing up cloud storage services like Dropbox and iCloud Drive because they use Apple's File Provider APIs, making files appear local without being fully downloaded. Users of Maestral, a Dropbox client that syncs to a regular local folder, report Backblaze still backs up their Dropbox content. Dropbox's own old-school client mode may also work, but results are inconsistent.

Apple's third developer betas of its version 27 operating systems introduce a built-in Uniform Type Identifier (UTI) for Markdown: `net.daringfireball.markdown`, which conforms to `public.utf8-plain-text`. The author has updated their own recommendation to match this UTF-8 encoding requirement.

John Gruber argues that Apple's strict enforcement of the squircle shape for all app icons, enforced via the App Store review process, stifles icon design creativity and should be eliminated, noting that shape was once a key part of an icon's identity.

Apple's iOS 27 developer beta 3 enables new "Pace" and "Expressivity" sliders for customizing Siri's AI voices, previously marked as "Coming soon." The article notes that after a month of testing, the default settings prove well-calibrated. Two new voices are available: one female and one male.

WorkOS Pipes offers a single API call to integrate with over 100 providers like GitHub, Slack, Salesforce, and Google Drive, handling OAuth flows, token refresh, and credential storage so developers can focus on product code instead of integration infrastructure.

A look at early Mac app icons shows Apple's convention of tilted rectangles and a hand icon. The author traces how this faded as users adapted, with apps like TeachText and Font/DA Mover breaking the mold, arguing that mandating design rules differs from organic adoption.

The ELIZA Archaeology Project documents the original 1960s MIT chatbot ELIZA, created by Joseph Weizenbaum. The project explores the program's code, history, and cultural impact, including the "Eliza Effect"—the human tendency to attribute intelligence to simple computer systems—which remains relevant to modern AI like ChatGPT.

The author recounts a recent interaction with a web-based recreation of ELIZA, the early AI chatbot, and shares a transcript of the stilted conversation. He expresses skepticism about ELIZA's historical reputation and criticizes anyone who found it useful as a virtual therapist, calling such people "suffered-a-permanent-head-injury wrong."

Ookla reports mmWave 5G remains mostly a U.S. and Verizon phenomenon. Verizon's mmWave appeared in 91 markets in late 2025, up from 75, while AT&T and T-Mobile lagged far behind. Speeds topped 1 Gbps, but coverage was limited to roughly 150 meters from transmission sites.

EveryMac.com, a site providing detailed information on every Mac model, celebrated its 30th anniversary in 2026. The milestone is noted alongside Daring Fireball's 24th anniversary, with DF's John Gruber reflecting on EveryMac's longevity, having launched in 1996 before Steve Jobs returned to Apple.

Safari Technology Preview 247 introduces the Safari MCP server, a Model Context Protocol server that lets AI agents connect to a Safari browser window to access DOM, network requests, screenshots, and console output for more autonomous web debugging and development.

The author revisits his 2022 decision to keep his iPhone on LTE to save battery life, noting that regular 5G offered no practical speed advantage over LTE. By 2026, he found himself back on 5G without a clear reason and has since switched back to LTE, recommending users try LTE day-to-day and enable 5G only for hotspot tethering or crowded venues.

The Lincoln Memorial Reflecting Pool, renovated for over $14 million by a Trump-connected contractor, quickly turned green with algae as its coating peeled. Critics say the failed project mirrors Trump's Washington, where the city has become a fenced-in, militarized construction zone ahead of the nation's 250th birthday, despite claims of beautification.

Truth Social remains an outlet primarily for Trump's own posts, while other administration officials continue using X. The platform functions as a blog-like channel for Trump's messages rather than a genuine social network competitor.

Anthropic says US export controls on Claude Fable 5 and Mythos 5 were applied June 12 and lifted June 30. The author argues this was performative nonsense, comparing Trump administration actions to "kayfabe" — treating staged events as genuine.

Meta's engineering culture is deteriorating under Mark Zuckerberg and Scale AI CEO Alexandr Wang, who have introduced keyboard tracking, reassignments to data labeling, and AI-centric performance metrics. Critics argue this incentivizes performative AI use, drives away experienced engineers, and contributed to a major Instagram hijacking incident caused by AI-written and AI-reviewed code.

MG Siegler was banned from WhatsApp for the third time in three years without explanation, shortly after claiming a username. He criticizes Meta's unreliable appeal process and notes that banned accounts still receive messages undetected by senders.

Hackers have been stealing Instagram accounts by asking Meta's AI support bot to link a target account to a new email address, without any verification needed. The AI sends a code to the attacker's email, which is then used to reset the password and gain full access. One victim only recovered his account after sending Meta's AI a link to a news article about the vulnerability.

The author contrasts two modems, noting that cellular download speed and reception are nearly solved for their needs, while battery life remains a significant issue.