In this episode, Michael admits he never called Apple—no surprise there—and shares what happened instead: experiments, frustrations, and the joys of not resetting VoiceOver live. Damashe breaks down his complicated relationship with to-do list apps, from OmniFocus quirks to why he’s sticking with Todoist (despite some platform inconsistencies).

We also dive into ChatGPT’s deep research mode and how Michael used GPT and Google Apps Script to streamline weekly workflows—what used to take hours now takes seconds. There’s talk of accessibility in Google Sheets and Docs, frustrations with VoiceStream Reader, and Bluetooth weirdness with Apple’s audio routing.

And yes, that one setting in Parallels that makes Mac/Windows integration so much better? We finally figured it out. You’ll want to hear this if you use SharpKeys and Keyboard Maestro.

Bonus rants: the B device still sucks, the Plod is promising, and surprise—your notifications don’t mean what you think they mean.

Links Mentioned:

• Review: “I Outsourced My Memory to AI and All I Got Was Fan Fiction” – The Verge
• Technically Working Tip Jar

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Michael shares some recent work slip-ups tied to automation and explains how a small formatting mistake threw off email quick links for thousands of people. He walks through how he’s checking Zoom links more carefully now using JAWS sounds and VoiceOver tweaks—and vents a bit about Apple's pronunciation settings and table editing headaches on the Mac.

Damashe jumps in with thoughts on where VoiceOver stands in Apple’s priority list (spoiler: not high), and they both trade tips for avoiding Safari freeze-ups and digging into macOS settings. There's also some behind-the-scenes talk about how automation projects are making them think more like coders, even if they’re just feeding prompts to GPT.

They talk about:

• Renting vs. buying speakers for events (and how hotel AV pricing is wild)
• Michael’s growing collection of smart appliances (yes, Sniffy McGee the vacuum makes a return)
• Network upgrade ideas, attic fails, and future cable runs
• Damashe’s vending machine script to automate reporting from Cantaloupe
• Using Hazel with GPT to build automation rules on the Mac

Toward the end, Michael shares a serious PSA about a family member who nearly fell for a phone scam—and why it's time to have a plan in place before you get a scary-sounding call. Damashe adds tips for protecting yourself as deepfakes and voice cloning get better and easier to pull off.

They wrap it up with a quick look at download numbers, what’s working with the “live to tape” style, and why Damashe regrets not buying that fancy Dyson fan when it was on sale.

Links & Mentions:

• Email us at feedback@technicallyworking.show
• Follow the show: @tw@technically.social
• Michael: @payown@dragonscave.space
• Damashe: @damashe@technically.social
• Use #TechnicallyWorking on Mastodon to chat with us
• And yeah—huge thanks to our tip jar supporters. You're the real MVPs.# Episode Notes

Notes go here

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This podcast is powered by Pinecast. Try Pinecast for free, forever, no credit card required. If you decide to upgrade, use coupon code r-431b7d for 40% off for 4 months, and support Technically Working.

Tired of bloated apps and broken automation? Damashe and Michael dig into the everyday tech that actually works—and what still needs fixing. From Todoist frustrations to FaceTime workarounds, they share tools and tips that make their workflows smoother. In this episode, Damashe and Michael talk through weather delays, podcast recording quirks, and the growing complexity of Zoom and Slack. They discuss how apps often overreach—like Zoom trying to do everything but its core job—and why Apple and Google are both struggling with balance. Michael shares why he's using Todoist again, the quirks of its Mac app, and details on his upcoming beginner workshop. They dive into RingCentral’s AI call summaries, SuperWhisper transcription workflows, Gemini’s privacy quirks, and how Tailscale can fake out your apps into thinking you’re always home. They wrap up with Android typing tips that might just change your life.

Support Technically Working by contributing to their tip jar: https://tips.pinecast.com/jar/technically-working

Find out more at https://technically-working.pinecast.co

Send us your feedback online: https://pinecast.com/feedback/technically-working/489c986b-df10-463e-9031-ff3bf5987f60

This podcast is powered by Pinecast.