Michael and Damashe begin with a look at how AI can turn convention documents into WordPress pages, Gravity Forms, confirmation messages, and other ready-to-use materials. They discuss why a smoother payment process matters and how showing people only the instructions they need can prevent abandoned registrations and unpaid entries.

Then Damashe reacts to rising Mac prices, explains why selling his MacBook Pro may have been a poorly timed decision, and considers whether things have become bad enough to buy another Windows computer. Michael shares useful shortcuts and recent experiences with Codex and ChatGPT, while both hosts stress that AI-generated work still needs to be reviewed.

The conversation also covers Postmark, Cloudflare, transactional email, and the decision to rebuild the Technically Working website with familiar WordPress tools. Damashe explains why he does not want his business depending on a software stack he barely understands. Along the way, the hosts offer a warning about installing several WordPress caching plugins and explain why more caching does not make a website faster.

Michael shares the latest Earshot improvements, including faster feed refreshes, haptic feedback, adjustable descriptions, new accessibility settings, and category browsing. The two consider how server-side podcast feed checking might work and what it could cost.

Finally, Damashe explains why the Technically Working Mastodon bot never appeared during the ACB convention. He secured the server so thoroughly that the bot could not get out. The planned solution involves a Raspberry Pi, Tailscale, and one more project competing for his attention.

• Using AI to build WordPress pages and Gravity Forms from existing documents
• Creating clearer registration and payment flows
• Why AI-generated forms and websites still need human review
• Rising Mac prices and Damashe’s poorly timed MacBook Pro sale
• ChatGPT and Codex shortcuts and computer control
• Postmark, AWS SES, and Cloudflare for transactional email
• Rebuilding the Technically Working website with GeneratePress
• Choosing a software stack you understand well enough to maintain
• Why several WordPress caching plugins will not make a site faster
• Earshot feed refresh, haptics, descriptions, and category browsing
• The possibilities and costs of server-side podcast feed checking
• Panic returning money to Playdate customers
• The mystery of subscriber number one
• How Damashe accidentally trapped the Technically Working bot
• Tailscale, Raspberry Pi projects, cameras, and internet failover

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Michael and Damashe explore what happens when AI tools are asked to work instead of simply answer questions. Damashe shares his experiences using ChatGPT to reorganize a Numbers spreadsheet, Claude to manage email, and an AI-assisted product search that produced a very convincing but completely inaccurate hard drive price.

That leads to a larger question: If you ask AI to research something, should you also have to tell it to search the web and verify the information? They discuss the rough edges of today’s AI agents, why this period feels like the early days of personal computing, and whether these tools will eventually become reliable enough to work without constant supervision.

They also talk about software companies rewarding new customers instead of loyal ones, VoiceOver and Zoom frustrations, sharing health data with AI, configuring ChatGPT and Codex on the Mac, repurposing computers as servers, and the photo they forgot to take when they finally met in person.

• Discounts for new customers versus rewards for existing customers
• VoiceOver keyboard commands that stop working until the Mac is restarted
• Using whois and dig to look up domain information
• Zoom’s loud and repetitive notifications
• Rising computer and storage prices
• Using ChatGPT to reorganize a Numbers spreadsheet
• Comparing ChatGPT computer use with Claude’s computer-control features
• Organizing email through Fastmail and MCP
• The permissions Codex needs to control apps on macOS
• An imaginary 24-terabyte hard drive deal that was too good to be true
• Why AI research should include checking the original source
• Whether we are living through the early personal-computer era of AI
• Asking one AI to review another AI’s work
• Giving AI access to Apple Health and years of health data
• Continuous glucose monitors and accessible glucose tracking
• Apple Watch reminders, workout encouragement, and handwashing alerts
• Customizing the ChatGPT app’s keyboard shortcuts
• Moving keyboard focus to the main chat composer with Shift+Escape
• Repurposing a Mac mini and mini PC as home and office servers
• Moving Plex and an audiobook library to Linux
• Why the show is not getting any shorter

• Gravity Wiz
• GeneratePress
• Fastmail
• Model Context Protocol
• Dexcom
• Audiobookshelf
• Plex
• Will Codex Reset?
• Pinecast

Send your feedback to feedback@technicallyworking.show.

• Michael: @payown@dragonscave.space
• Damashe: @damashe@technically.social
• Technically Working: @tw@technically.social

Join the conversation using #TechnicallyWorking.

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Michael and Damashe are back after St. Louis with an episode that runs long on opinions. Michael shares early Earshot numbers, explains why he is building iCloud sync with privacy defined up front, and walks through why the iOS simulator makes VoiceOver testing nearly impossible. Damashe lays out his solution for Meta and everyone else building smart glasses: stop using disabled people to justify features you should not ship the way you are shipping them.

Also in this episode: switching from Terminal to the Codex app, whether Stage Manager could replace virtual desktops, Todoist versus Reminders, the trick to actually remembering names, and a plan to smoke chili on Sunday.

• Recapping the shortest show they have ever published, recorded in person in St. Louis
• Earshot on the App Store: 249 downloads, 40 subscriptions, and zero marketing so far
• Why Michael is cautious about third party subscription analytics and what data is actually available in App Store Connect
• The tradeoffs of Apple standing between developers and customers
• iCloud sync coming to Earshot: library, queue, play position, and bookmarks, with the help screen spelling out exactly what gets stored
• Stress testing with an OPML file of 1,100 feeds and an inbox that pulls in 3,000 episodes every other day
• Refresh performance and where concurrent feed checking comes in
• Why Michael is not asking for reviews inside the app, and Damashe's case against review prompts that interrupt you
• The VoiceOver experience in the iOS simulator, and why "heading, heading, heading" made Michael start pushing developer builds straight to his phone
• What this means for sighted developers who want to build accessible apps
• Accessible screen sharing on the Mac, the voice pitch quirk, and canceling a remote access subscription
• Damashe's take on smart glasses, person recognition, and why contacts should be the boundary instead of a social graph
• Whether AI should describe people at all
• Saying someone's name five times so you actually remember it
• Michael's move from Terminal to the Codex app, plus a good experience with Claude Cowork
• Could Stage Manager work as a virtual desktop for a VoiceOver user? Neither of them knows, so tell them
• Beta features in shipped builds, and using smaller TestFlight groups to absorb schema migrations
• Todoist, Reminders, Fantastical, and getting AI chats to file reminders for you
• Perspective Tasks as a free option worth a look
• What an operating system might look like if it were just an edit box, and why Damashe is not sold

• Earshot on the App Store
• Perspective Tasks by Michael Doise and Taylor Arndt
• Stage Manager on macOS: if you use it with VoiceOver, they want to hear from you

Email the show at feedback@technicallyworking.show

Michael on Mastodon: https://dragonscave.space/@payown Damashe on Mastodon: https://technically.social/@damashe The show bot: https://technically.social/@tw

Use the hashtag #TechnicallyWorking, and capitalize the T and the W so screen readers say it correctly.

One time tips and monthly subscriptions are both available at https://technicallyworking.show, under the support us link. Shout out to subscriber number one, whoever you are.

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Check out our podcast host, Pinecast. Start your own podcast for free with no credit card required. If you decide to upgrade, use coupon code r-431b7d for 40% off for 4 months, and support Technically Working.