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#177 – The Bot Couldn’t Get Out episode artwork

Sep 1, 2026 1 hr 16 min

#177 – The Bot Couldn’t Get Out

from Technically Working

Technically Working 177: The Bot Couldn’t Get Out Show Notes 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. In This Episode 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 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/ba76eb96-515b-4c08-9587-0684eae26143 Check out our podcast host, Pinecast. Start your own podcast for free with no credit card required.

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#177 – The Bot Couldn’t Get Out

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CISO Perspectives (public) N2K Networks This season on CISO Perspectives, host Kim Jones explores some of the challenges of leading through uncertainty. We explore the complexity of the changing nature of regulation and working with the federal government, the evolution of privacy and fraud, and how emerging technologies like AI and quantum computing are changing cyber. When you don’t know what questions to ask, you’re afraid to ask, or don’t know who to ask, CISO Perspectives provides the foundation for learning in this brave new world. The Regular Man Podcast The Regular Man Podcast Welcome to the Regular Man Podcast, where we celebrate God's gift of masculinity in the life of the Regular Man. Here, there are no pastors, no pretense, and no pandering. Just interesting conversation, realistic expectations, and practical advice for the regular man. Steve Cruz is the host of The Regular Man Podcast, created specifically for the regular, hard-working, blue-collar man. He’s a husband and father who believes men should embrace God’s gift of masculinity and live a life of Christian virtue. Steve learned the value of hard work, integrity, and respect through an upbringing of cars, construction, and a cadre of strong hardened men. As a military veteran and law enforcement officer, Steve understands the value of speaking directly and plainly on subject matters that are, far too often, nuanced to death by the modern-day Christian Church. As the host of The Regular Man Podcast, Steve has down-to-earth

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This episode was published on September 1, 2026.

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