Windows Weekly (Audio) - Episode WW 945: "Vermont? Seriously? - GitHub CEO Resigns as CoreAI Takes Over"

Released on August 13, 2025

Hosts:

• Leo Laporte
• Paul Thurrott
• Richard Campbell

I. Patch Tuesday and Windows Updates [02:35 - 07:09]

The episode kicks off with a deep dive into the recent Patch Tuesday, highlighting crucial updates for Windows 10 and the integration of AI features into the operating system. Paul Thurrott expresses frustration over the growing disparity between users with CoPilot PCs and those using standard Windows 11 installations. He remarks,

"It seems like there's a world of haves and have-nots now. The haves are the people with CoPilot PCs who get all these additional features, and the have-nots are the lowly peons that just have normal Windows 11 like losers." [04:28]

Richard Campbell adds to the discussion by pointing out the historical schism within Microsoft between teams developing online products and on-premises solutions:

"There's also a schism between the folks that are working on the online product, which is the primary product. So the best of the best are there. That's probably true." [03:06]

The conversation underscores the challenges Microsoft faces in maintaining and updating diverse product lines, balancing innovation with reliability.

II. Windows 10 End of Support and Extended Security Updates [10:44 - 19:23]

Transitioning to Windows 10, the hosts discuss Microsoft's decision to end support for the OS in October 2025. For the first time, Microsoft is offering an Extended Security Updates (ESU) program for consumers, priced at $30. Paul notes the company's strategic maneuver to mitigate potential class-action lawsuits:

"They have answered why? Because they're going to do everything they can to give this to you. It's fine, you know." [18:18]

Additionally, Microsoft has committed to supporting the Edge browser on Windows 10 until October 2028, ensuring users continue to receive browser updates and features post-OS support. Leo comments on the reliance on browsers as a determining factor for the continued usability of older operating systems:

"Technically, my experience has been you don't have to really give up on our operating system until you can't get browsers for it." [19:13]

This segment highlights Microsoft's efforts to extend the lifespan of Windows 10 while gently nudging consumers towards newer OS versions.

III. Microsoft's AI Integration and GPT-5 [07:09 - 45:31]

A significant portion of the episode delves into the advancements and controversies surrounding AI, particularly focusing on OpenAI's GPT-5 and its integration into Microsoft's ecosystem. Paul Thurrott elaborates on Microsoft's initiative to make AI programmable within applications:

"One of the little themes this week and then for the rest of our lives is going to be how AI becomes kind of programmable, if that makes sense." [05:25]

The hosts discuss the rollout of AI features in Windows Settings, allowing users to control system settings via natural language commands. Paul emphasizes the potential and limitations of such integrations:

"Now you can use natural language to talk to it and say, you know, I want to make the screen dark, I want to do whatever." [05:25]

The conversation shifts to the release of GPT-5, with Leo expressing mixed reactions to its reception and performance. Paul criticizes the inconsistency in AI responses, highlighting the model's unpredictability:

"What you see is fine. Whatever you see is exactly what's supposed to be there. I hate this so much." [09:07]

Despite these concerns, the hosts acknowledge the transformative potential of AI in various applications, from coding assistance to enhancing user interfaces.

IV. AI-Powered Browsers and the Future of Web Interaction [33:00 - 87:22]

Exploring the intersection of AI and web browsers, the hosts examine emerging AI-powered browsers such as Comet, DIA, and Microsoft's Copilot Mode in Edge. Paul demonstrates how these browsers integrate AI to streamline tasks, such as generating weather updates or managing system settings through conversational interfaces.

Richard Campbell raises concerns about data privacy and the implications of AI-controlled browsers:

"Now that I'm home, I'm going to take a look at this because I've been doing this for a long time. And I had... But yeah, I don't know if there." [113:35]

The discussion highlights both the convenience and potential vulnerabilities introduced by AI-driven browser functionalities, emphasizing the need for critical evaluation and trust in AI-generated responses.

V. GitHub CEO Resignation and CoreAI Takeover [101:16 - 123:35]

In a landmark development, the episode addresses the resignation of GitHub's CEO, Thomas Demke, and the subsequent absorption of GitHub into Microsoft's CoreAI division. Paul provides a historical context, tracing the leadership changes within GitHub and Microsoft's strategic realignment towards AI-centric operations.

Richard Campbell offers insights into the organizational shifts, noting Microsoft's attempts to consolidate AI expertise under CoreAI:

"But what Rich, you said, like, what's the dynamic here? And I think it's similar. It's like, look, we're looking at a world that's going to be different than the world today." [106:22]

The hosts speculate on the implications of this move, suggesting that Microsoft's centralized AI strategy may streamline operations but also raise concerns about autonomy and innovation within GitHub.

"It's similar to the work Microsoft did 30 plus years ago on DDE and then Olay and then Comm and whatever has come since then." [107:06]

This segment underscores the evolving landscape of software development platforms under the influence of AI giants.

VI. Whiskey Segment: Union Horse Distillery [99:46 - 171:43]

Departing from technical discussions, the hosts share a personal segment on experiencing American single malt whiskey from Union Horse Distillery. Richard Campbell narrates the distillery's journey, detailing their brewing processes and the introduction of the American single malt standard by the Alcohol, Tobacco and Taxation Bureau in January 2025.

Paul and Leo engage in a lively discussion about the nuances of the whiskey, praising its craftsmanship and regional influences. The segment highlights the resurgence of local distilleries embracing traditional methods with modern innovations.

Richard recounts the distillery tour, emphasizing the challenges of working with rye and the meticulous care in crafting their products:

"He's like, this is your personal assistant. Like it you." [98:57]

The episode celebrates the rich heritage and community-driven efforts in the craft whiskey industry, providing listeners with an engaging and informative break from the predominant tech focus.

VII. Closing Remarks and Community Engagement [171:14 - 175:03]

In the concluding segment, Leo Laporte encourages listeners to engage with the Windows Weekly community through various platforms, including Discord and YouTube. He emphasizes the value of community support and the benefits of becoming a club member to access exclusive content and show features.

"If you like these Whiskey segments, there's a whole passel of them in there. And we're keeping that up to date. I think we're almost up to 100." [170:56]

Paul and Richard share final thoughts, reiterating the importance of critical thinking in the age of AI and the enduring relevance of traditional resources like libraries. The hosts express gratitude towards their audience and preview upcoming topics for future episodes.

Notable Quotes

• Paul Thurrott at [04:28]:

  "It seems like there's a world of haves and have-nots now. The haves are the people with CoPilot PCs who get all these additional features, and the have-nots are the lowly peons that just have normal Windows 11 like losers."

• Richard Campbell at [03:06]:

  "There's also a schism between the folks that are working on the online product, which is the primary product. So the best of the best are there. That's probably true."

• Paul Thurrott at [05:25]:

  "One of the little themes this week and then for the rest of our lives is going to be how AI becomes kind of programmable, if that makes sense."

• Leo Laporte at [19:13]:

  "Technically, my experience has been you don't have to really give up on our operating system until you can't get browsers for it."

• Richard Campbell at [106:22]:

  "So my guess here is that they told Thomas Demke he'd now be reporting to Jay and he said how about no?"

Conclusion

Episode WW 945 of Windows Weekly offers a comprehensive exploration of Microsoft's latest updates, the integration of AI into its ecosystem, and significant organizational changes within GitHub. The hosts balance technical analysis with personal anecdotes, such as their experiences with craft whiskey, providing a well-rounded and engaging listen. Key discussions emphasize the transformative yet challenging role of AI in technology, the implications of ending Windows 10 support, and the strategic realignments within major software platforms like GitHub.