Windows Weekly 967: 2nd-Generation Bonobos – Windows 11 Gets Emergency OOB Update!

Date: January 21, 2026
Hosts: Leo Laporte, Paul Thurrott, Richard Campbell
Podcast: Windows Weekly

Episode Overview

This episode dives deep into Microsoft’s recent emergency out-of-band (OOB) patch for Windows 11, Satya Nadella’s relentless AI push, ongoing confusion and frustration around Windows 11’s OneDrive folder backup, expanding Xbox gaming experience on ARM devices, and the broader discontent with big tech’s business models and AI mania. The trio round out the conversation with cultural commentary, reflections on Microsoft’s organizational evolution, and a fascinating liquor pick centered on the rich tapestry of Mexican agave spirits.

Key Discussion Points and Insights

1. Emergency Out-of-Band Windows 11 Update: “Two Non-Story Stories”

Timestamps: [03:38]–[10:52]

• What Happened?

  • January 2026’s Patch Tuesday introduced a bug affecting enterprise and education customers, breaking Remote Desktop connections and causing some machines to reboot instead of shutting down/hibernating ([04:09]).
  • Home and Pro users were not affected. “It didn’t really impact too many people, and it’s been fixed, so I guess we’re okay,” summarized Paul ([04:09]).

• Media Coverage and Social Media Hype

  • Paul: “It got everywhere... I know it got everywhere. It's like a Family Circus cartoon. Right. You see a blue screen in an airport or a train station and you're like, oh, Windows, there it goes again” ([06:35]).
  • The trio lamented the disproportionate coverage of minor glitches—“two non-story stories” ([07:29]).
  • Leo pointed out the YouTuber Linus Tech Tips experienced the issue; Paul rolled his eyes, “Oh, perfect. And he definitely in any way… Windows sucks. Oh, well, you’re using Windows so much. I don’t know, whatever. But it's just... this is the world I live in.” ([09:15])

• Richard’s Theory

  • “This is almost certainly an exotic GPO security problem,” meaning it’s not a widespread home user issue, but about enterprise security policies ([05:12]).
  • The team suspects Microsoft's recent internal reorganizations may temporarily lead to more update hiccups ([05:27]).

2. The OneDrive/In-Your-Face Backup Debacle

Timestamps: [12:00]–[18:57]

• The Issue:

  • Microsoft has been turning on folder backup in OneDrive (Desktop, Documents, Pictures) in Windows 11—even after users have explicitly said no, sometimes multiple times ([12:00]).
  • Paul: “There were screens where you could say no… and then [Microsoft was] just turning it on anyway. … If there is no better version of insertification than THAT, in my opinion.” ([12:53])

• Recent Changes:

  • Microsoft now prompts users to choose whether to keep files in OneDrive or move them back locally when disabling sync—a “half-step” improvement, but with caveats ([15:51]).
  • This still requires users to know exactly when to hit “no” in the setup flow or miss their window; Paul calls this a "hidden UI" and criticizes Microsoft for not communicating such changes ([18:57]).

• Broader Implications:

  • “Anything that's kind of a dramatic change… you should be told about it… and [should] opt in,” says Paul, comparing OneDrive’s approach unfavorably with recent forced opt-in AI features ([16:55]).
  • Richard notes these patterns feel “malicious” and breed deep distrust ([19:43]).

3. Windows on ARM and Xbox App Evolution

Timestamps: [20:13]–[27:33]

• State of Play in 2026:

  • The Xbox app for Windows 11 on Snapdragon X-based ARM devices—originally limited to cloud streaming—is now out of Insider-only status, letting users browse, download, and play supported games locally ([20:13], [21:17]).
  • Microsoft is (belatedly) adding performance ratings to indicate which titles actually function on ARM, a feature Paul and Richard had long called for ([23:26]).

• Still Room for Improvement:

  • “They should be highlighting this. This is a commitment to the customer. This is how you tell us that you’re serious about ARM,” Richard argued ([24:30]).
  • Paul: “This should have shipped on day one… but this is better.” ([25:08])

• The Challenge:

  • Paul delights in his ARM laptop’s seamless waking and battery life versus high-end Intel machines that feel unpredictable and buggy ([26:06]).

4. Windows Insider Channels, Organizational Stuckness & “Second-Generation Bonobos”

Timestamps: [30:13]–[38:13]

• Insider Channel News:

  • A unique build hit only Beta (not Beta+Dev) for the first time, suggesting preparations for the next major Windows version ([30:18]).
  • Canary, now aligned to 26H1, still shows no meaningful new features—fueling skepticism about its actual purpose ([32:11]).

• Organizational Analysis:

  • Paul & Richard riff on Microsoft’s cultural inertia, likening staff to “second-generation bonobos” in a famous behavioral study—beating down new ideas out of institutional memory, even after the original reasons are forgotten ([36:41]).
  • “It takes time to grow up a set of leaders who know how to work across teams,” Richard observes, empathizing with the post-Windows-as-king reality ([38:13]).

5. The Broader “Insertification” of Tech & The AI Obsession

Timestamps: [59:30]–[86:47]

• The Big Rant: Microsoft, Apple, & ‘Making Money on You’ Instead of for You:
  • Paul argues Microsoft is no longer a tech company, but a “money management real estate company that also has tech” ([60:29]).
  • Microsoft's and Apple’s relentless pursuit of recurring revenue (subscriptions, “average revenue per user”/ARPU, AI features behind paywalls) drastically changes their relationship to customers ([59:07]).
  • “If you care about your soul… it would be painful. The best thing that could happen to our industry… would be for this [AI] bubble to blow up in their face and for them to go back to doing things that benefit their customers” ([73:14]).

Notable Quote:

“It’s not just insertification, it’s insertification with cancer. It’s with cancerous growth. It’s insertification exponential.”
— Paul Thurrott ([65:59])

• AI Skepticism & Disillusion:
  • “Copilot has not resonated with almost anybody. GitHub Copilot being the exception,” says Paul ([89:51]).
  • Richard: “We are forced to make stupid decisions because of this bubble effect. I’d like to get over it because I got stuff to get done.” ([72:29])
  • AI benefits are often lateral, or “the things you used to get for free because you were already a customer” ([70:48]).

6. The Linux “Escape Hatch” and Cross-Platform Cultural Commentary

Timestamps: [49:01]–[55:47]

• Windows-on-Linux Future?

  • Paul discusses growing viability of Linux as a day-to-day desktop for former Windows users, though faulting cloud sync as the last big barrier ([49:01]).
  • “Maybe Windows is the GUI Linux has been looking for all its life,” Richard quipped ([52:08]).

• Apple’s Growing Lockdown and Subscription Model:

  • Leo rails against Apple’s UI “impositions” (liquid glass) and its expanding service lockdown, expressing discomfort with both major ecosystems ([55:55]).

7. “Move Fast and Break Things” at Microsoft—A Damaging Mindset

Timestamps: [88:13]–[90:24]

• Microsoft rushed Copilot AI into all its products before the tech, policies, or experience were ready; necessary opt-outs and admin controls came much later ([88:13]).
• “Move fast and break things works when you’re a startup... but when you’re Microsoft, what your customers want is for you to move deliberately and don’t break anything” ([89:22]).

8. AI News Bites

Timestamps: [91:08]–[95:48]

• ChatGPT Go:

  • Now available globally as a cheaper, but ad-supported, alternative for markets needing lower-priced access ([91:08]).

• Wikipedia Strikes Deals with Big Tech:

  • The Wikimedia Foundation is now licensing access to big tech (Amazon, Meta, Microsoft, Mistral, Perplexity, etc)—not OpenAI so far. Some community contributors object, but Paul points out all AI was already scraping Wikipedia regardless ([92:59], [95:43]).

Notable Quotes & Memorable Moments

• On Buggy Updates:

  • “The vast number of installs work just fine. … Like the vast majority of planes land just fine. You know, it’s like the problem, you know, we got to be careful.” — Paul ([08:30])

• On Microsoft's Changing Customer Relationship:

  • “You used to pay for the product, and you got value. Now, we’re not playing the same sport.” — Paul ([67:09])

• On “Insertification”:

  • “Insertification is a company that is literally harming its own customers and partners to advantage itself. Because that makes economic sense, by the way.” — Paul ([65:59])

• On the AI Bubble:

  • Richard: “If more people don’t use AI, the bubble might burst.”
    Paul: “The bubble needs to burst. I really do. I think the best thing that could happen to us.” ([72:02])

Timestamps for Key Segments

| Timecode | Segment Description | |-----------|-----------------------------------------------------------------------| | 03:38 | Start of Patch Tuesday OOB update discussion | | 12:00 | OneDrive backup controversy - Microsoft enabling after user declines | | 20:13 | Windows on ARM, Xbox app experience | | 36:41 | “Second generation bonobos” – organizational inertia at Microsoft | | 59:30 | Apple & Microsoft’s “insertification”: subscription, ARPU, control | | 65:59 | Paul’s rant: “[Insertification] with cancer…” | | 70:48 | How AI features are monetized now vs old feature updates | | 82:11 | Lockdowns, DRM, and right-to-repair | | 88:13 | Microsoft’s move-fast-break-things mindset with Copilot | | 91:08 | ChatGPT Go and AI platform news | | 97:09 | Xbox section: Bungie’s Marathon, Xbox on ARM, Game Pass titles | | 133:03 | Liquor Pick: Raicilla (Mexican agave drink) – history & context |

Back of the Book

Security Tips (Paul's Corner) [117:13]

• On securing Microsoft accounts: Always enable two-step authentication, use passkeys, and use the Microsoft Authenticator app for Microsoft accounts. For general accounts, Proton Authenticator is the best free, open-source, fully encrypted option ([117:13]).
• Passkeys: The most efficient and secure option with Windows Hello, autofill, etc. ([121:06])

Local AI Apps for Windows [125:54]

• Microsoft AI Dev Studio: A preview app for developers showing off what’s possible with local AI models (text/image/audio/video) on Windows. Paul: “It's astonishing how many AI-based capabilities are in there. It's worth looking at.” ([130:49])

Richard’s Liquor Pick: Raicilla (Racía) [133:03]

• History Lesson: Raicilla is a centuries-old agave spirit from Jalisco, Mexico, made to dodge taxes and regulatory “tequila” definitions ([145:45]).
• Taste Profile: Botanical, not peppery; “a gin you would drink neat. Rich, no heat, 40%—it would be a sin to put this in a cocktail… It's so nice by itself.” ([151:07])
• How to Find: Look for an “Anastasia distillery” bottle at specialty stores ([145:07])

Episode Tone & Language

• Candid, at times frustrated or exasperated (especially Paul), peppered with wry humor and a sense of deep engagement with the ongoing changes—and challenges—of the tech world.
• Notable for strong language around corporate practices: “insertification,” “malicious,” “with cancerous growth,” “money management company,” direct critiques of Microsoft and Apple (and to a lesser extent, Google).
• Also includes playful digressions: nautical boathouse jokes, reminiscing about Scottish breakfasts and ‘organ meats,’ and a genuinely engaging agave liquor history lesson.

In Summary

This episode offers a wide-ranging, often searingly honest look at the state of Microsoft and big tech in 2026: Windows update drama (or non-drama), aggressive data/feature insertions, ARM progress, industry AI hype and malaise, and underlying business shifts—intertwined with cultural and historical tangents, delivered in the dynamic, familiar banter of three veteran hosts.