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September 7, 2025 76 mins

In this episode of Technically Working, Michael and Damashe dive into email management frustrations and fixes. From 1Password’s latest quirks with VoiceOver on iOS to hidden keystrokes in Mac Mail, they share practical tips to keep your inbox manageable. Michael experiments with Keyboard Maestro to make the delete key archive instead of trash, while Damashe drops shortcuts you probably didn’t know existed.

They also chat about UPS shipping tricks, buying gear on eBay without getting burned, and whether Apple is overreaching—or finally catching up—in AI. With Apple’s September event on the horizon, the guys weigh in on what’s coming with new iPhones, Watches, and maybe even AirPods with health tracking.

Got a take on the next iPhone or a favorite automation trick? Reach out and let us know what’s working for you.

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