WW 997: Bear Swamp & The Boathouse - New Context Menu Customization Debuts for Insiders

WW 997: Bear Swamp & The Boathouse - New Context Menu Customization Debuts for Insiders

Author: TWiT August 19, 2026 Duration: 2:30:32

For years, the checkbox to get a PC out of the Insider Program when that Windows version shipped in stable did absolutely nothing. That's no longer the case.

Windows

  • A new context menu for File Explorer heads out to Insiders along with five new preview builds
  • There are lots of other like UX changes happening with little communication. Will Microsoft really touch (and update) all the ancient UIs in Windows 11?
  • New Release Preview builds point at next Week D and Patch Tuesday updates: New Taskbar, New Start, new Windows Search, many minor changes throughout

Hardware

  • Now we know more about Snapdragon C ahead of IFA, where we may see the first laptops
  • Google is holding a PixelBook reviewers event in mid-September
  • You know that Commodore is back, but now the Amiga is back too!
  • Lenovo surges on AI spending, but it's now engaged in financial shenanigans too. More like Spotify than Big Tech, but still bad

AI

  • Big Tech spending on AI is finally getting more scrutiny from financial/business publications
  • It's happening: Microsoft "pulls a Teams" and will consolidate its Copilot (consumer) and Microsoft 365 Copilot (business apps) into a single app, evolve it in a "super app"
  • OpenAI's new strategy: Get 'em while they're young
  • Mozilla provides a progress report on Smart Window for Firefox, details new AI search partnership
  • Alexa+ is now free on all FireTV devices in the U.S., no Prime required

XBOX

  • Resonance: A Plague Tale and more are heading to Game Pass during the second half of August
  • XBOX August Update is here with more Achievements details, Game Hubs now support Xbox 360 titles, Game Pass subscribers can now stream a game while it installs in the background
  • XBOX Insiders can now test Home Improvements, local save game management, and profile badges
  • Apple makes major App Store concessions in the EU. But Epic Games says it is not enough.
  • The new Call of Duty has a public beta on Friday, and there will be a single-player episode for the first time

Tips and picks

  • Tip of the week: Yes, Virginia, you can exit the Insider Program now
  • App pick of the week: Brave
  • RunAs Radio this week: Automatic Attack Disruption with Liz Tesch
  • Brown liquor pick of the week: Red Bank Premium Blended

Hosts: Leo Laporte, Paul Thurrott, and Richard Campbell

Download or subscribe to Windows Weekly at https://twit.tv/shows/windows-weekly

Check out Paul's blog at thurrott.com

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For anyone following the vast and often intricate ecosystem of Microsoft, Windows Weekly (Video) offers a consistently insightful look behind the curtain. Hosted by Leo Laporte of TWiT, the conversation is driven by veteran Microsoft insiders Paul Thurrott and Richard Campbell, whose combined expertise provides context that goes far beyond surface-level news. While the name suggests a focus on the operating system, this podcast truly serves as a comprehensive analysis of the entire company, from its consumer-facing products like Xbox and Surface to its massive enterprise cloud services and ambitious AI initiatives. Each episode feels like a detailed briefing, unpacking the strategies, successes, and stumbles of the tech giant. The video format adds a valuable layer, allowing you to see the hosts' reactions and follow along with screen shares when they delve into technical previews or software updates. You'll hear informed speculation, historical perspective, and critical debate about Microsoft's direction, making it an essential resource for IT professionals, developers, and dedicated enthusiasts who want to understand not just what is happening, but why. This is the kind of deep dive that turns complex topics into engaging discussion, offering the only Microsoft analysis you'll likely need. For those who prefer an uninterrupted experience, ad-free audio and video feeds are available through Club TWiT.
Author: Language: en-us Episodes: 33

Windows Weekly (Video)
Podcast Episodes
WW 992: Gassy Jack - Largest Patch Tuesday in Microsoft History! [not-audio_url] [/not-audio_url]

Duration: 2:32:12
Microsoft's July 2026 Patch Tuesday just shattered records with hundreds of bug fixes, and AI is the force behind the surge. Are we witnessing the beginning of a safer Windows, or is this flood of vulnerabilities the new…
WW 990: Don't Be Nostalgic for Stupid - The Doom & Gloom Watch [not-audio_url] [/not-audio_url]

Duration: 2:39:55
Windows 10's Extended Security Update program quietly gets extended for another year for consumers. Microsoft reportedly kills Surface Go products & is now selling 8 GB Surface Pro & Laptop models. And Xbox Series X & S…
WW 989: Deer Hate MSDN - Point-in-Time Restore Arrives for Windows 11 [not-audio_url] [/not-audio_url]

Duration: 2:41:44
Windows 12 is stalled and the real reasons go far beyond software. The conversation unpacks how soaring hardware prices, AI chaos, and market confusion have Microsoft in a holding pattern. Also, Paul finally took a sledg…
WW 988: Bubbleable - XBOX Could Be Facing a Moment of Reckoning [not-audio_url] [/not-audio_url]

Duration: 2:51:13
With major leadership shakeups and rumors of studio closures, the future of XBOX inside Microsoft suddenly looks uncertain. Is this the beginning of a Game Pass overhaul, or could XBOX face an outright split from the com…
WW 986: Liminal AI - RTX Spark, Project Solara, Scout, & Much More! [not-audio_url] [/not-audio_url]

Duration: 2:32:00
Build 2026 is underway in San Francisco this week, and it started with a big, overly-long keynote as always. And Computex is this week, too. There's a lot going on, and some of it is fascinating. Plus, WWDC is next week…