Windows Weekly 967: 2nd-Generation Bonobos

January 21, 2026 — Hosts: Leo Laporte, Paul Thurrott, Richard Campbell

Episode Overview

This episode opens with the usual relaxed chemistry between Leo, Paul, and Richard—from discussions of boathouse life and organ meats to the latest happenings in the Windows world. The core themes focus on Microsoft’s recent "out of band" Windows patch issues, the company’s relentlessly growing embrace of AI under Satya Nadella, the evolution of Xbox Game Pass on ARM PCs, critiques of insertification (the trend of tech giants making life harder for users to benefit themselves/Wall Street), and a healthy side of tech culture ranting. Plus, a typically epic "liquor pick" segment explores the rich and little-known history of Racia, a moonshine-esque Mexican spirit made from agave.

Key Discussion Points & Insights

1. Boathouse Banter & Herring Anecdotes (00:53—03:38)

• The hosts open with lighthearted, location-driven chatter. Richard details living in his glass-walled boathouse with its foggy, gray-box ambiance and daily wildlife spectacles:
  • "Everybody eats the herring."
• Scottish breakfast, organ meats, and using oatmeal to make everything better.

2. Microsoft January Patch & "Non-Story Stories" (03:38—08:55)

• Paul explains a recent Microsoft Windows update debacle that caused:
  • Remote Desktop (RDP) sign-ins to fail.
  • Unprompted computer reboots on hibernation or shutdown.
• Impact limited to enterprise/education customers. No home/pro users severely affected.
  • [04:09] "Very typical for our community...got a lot of play, but didn’t really impact too many people." (Paul)
• Richard suspects a GPO (Group Policy Object) security misconfiguration.
  • [05:12] "This is almost certainly an exotic GPO security problem." (Richard)
• The story’s significance is questioned—framed as media blowup over niche issues.

3. RDP’s Struggles & Microsoft’s Legacy Burden (09:04—11:57)

• Declining but stubborn RDP usage in enterprise.
  • [10:08] "This is Microsoft’s cross to bear, you have to support all these old legacy things..." (Leo)
• Modern Windows actively discourages typical users from setting up RDP, so only power users feel the pain.

4. "Insertification," Self-hosting, and the Everyday Carry Rant (11:57—12:56)

• Paul rails against the trend of labeling everyday objects as tech lifestyle ("everyday carry") and the related self-hosting obsessions:
  • [11:16] "I literally get a creepy feeling up my back when I hear that term...What are you, a superhero?" (Paul)

5. OneDrive "Folder Backup" Controversy (12:56—19:21)

• Microsoft quietly enables OneDrive Desktop/Documents/Pictures folder backup in Windows 11/10—even after users say "no".
  • [12:53] "What they are doing is just turning it on anyway." (Paul)
• Turning off folder backup is cumbersome and creates misleading shortcuts instead of restoring the old structure.
• Recently, a partial fix: users get a prompt to move files back locally or leave them in OneDrive.
  • [13:54] "It’s a half step in the right direction...but you have to know where to look." (Paul)
• Still opt-out, confusing, and potentially storage-filling for unsuspecting users.
  • [16:13] "If you don't have enough storage, it will give you an error." (Paul)
• Discussion tied to Microsoft’s overall pattern: "Insertification"—quietly shifting user control in service of their business goals.

6. Xbox Game Pass & Windows on ARM: Progress & Problems (20:13—25:33)

• Windows 11 on ARM (Snapdragon X) originally could only stream games, not download from Store; more recently, users can browse/download, but curation is imperfect.
  • [21:11] "It should be a curated experience…only show the games compatible with this computer." (Paul)
• Now, Xbox app on ARM highlights which Game Pass games "fit" your device’s performance.
  • [23:26] "Microsoft says 85% of the games in the Game Pass catalog are compatible with ARM-based PCs." (Paul)
• Frustration at the lack of clear marketing to explain and celebrate this progress.

7. The Great AI Rush & Microsoft’s Insertification Problem (35:51—77:44)

• Satya Nadella’s strategy: AI everywhere, even when the value to the customer is dubious.
• Wall Street drives decisions; real innovations or customer desires less relevant.
  • [67:29] "They’re selling us on this vision where the thing that makes that possible...today requires an astronomical financial investment." (Paul)
• Criticism of AI "bubble": Businesses buy AI tools uncritically, with zero attention to actual productivity gains for users or developers.
  • [74:13] [Richard paraphrasing a meme] "Nobody’s checking...It's not being measured..."
• Open skepticism that any of this makes sense outside of investor optics.
  • [73:44] "I think the bubble needs to burst. I really do. I think the best thing that could happen to us..." (Paul)
• Good AI exists, but not in the everyday features being heavily marketed. Sentiment that the field is vastly overhyped.
  • [86:08] "My point is they're overemphasizing this so much that they have turned it into something only the richest companies in the world can do." (Paul)

8. Linux as a Windows Successor? (50:32—56:05)

• Leo brings up the prediction Microsoft could "do the funniest thing imaginable" and replace Windows with a Windows-themed Linux.
  • [50:42] "'I predict...Microsoft will discontinue Windows in favor of a Windows-themed Linux distribution.'"
• Paul: Today, that's actually "extremely doable"—compatibility and UX issues have lowered over time.
• Workflow inertia is the real obstacle, not technical feasibility.
• GUIs and platforms have converged.
  • [55:11] "GUIs have kind of converged. Even Mac has become more and more Windows-like." (Leo)

9. App/OS Insertification: Apple, Microsoft, and the Path to Lock-In (57:00—63:16)

• Apple criticized for rigid UI changes (Liquid Glass), hard security lockdowns, dev restrictions, and push toward subscription services, affecting user freedom and customization.
  • [57:36] "It reduces accessibility...this is an example of a company imposing its will on its users." (Leo)
• Microsoft and Google push subscription lock-in too, shifting basic consumer value to recurring revenue.
  • [60:56] "That's more and more the focus—not are we selling a lot of Macs..." (Leo)

10. Company Purpose: Investor Management vs. User Value (64:54—67:12)

• Paul and Richard agree that Microsoft is now, fundamentally, a "money management real estate company"—just as Google is an ad company.
  • [64:54] "Microsoft is a money management real estate company that also has tech and infrastructure..."
• Amy Hood (CFO) and financial engineering now run the show; product direction is secondary.

11. SME Tech Culture: Second-Generation Bonobos (38:12—40:12)

• Richard tells the "second-generation bonobos" story to illustrate how cultural inertia—and learned helplessness—persists within tech organizations.
  • [39:03] (Richard) "[T]hey've removed all of the bonobos that ever got wet, but the ones that are there still beat the hell out of every newcomer who dares to touch that ladder."
• "15 years on is not that long for cultural change"—old institutional habits die hard.

12. Windows Insider News & Modernization (41:47—43:29)

• Paul briefly describes subtle UI improvements in the Windows Insider builds (modernized account dialogs).
• Canary channel remains "an orphan," with Richard hoping for positive updates due to recent team reorganizations.

13. Notepad & Paint: Genuine Upgrades or Faux Progress? (43:29—47:35)

• Notepad gets Markdown and a "Welcome" experience; most new features are opt-out.
• Paint: New features (like "Coloring Book") increasingly require Copilot Plus (MPU-equipped) PCs—some are underwhelmed.
  • [46:45] "It's called Coloring Book...you can prompt it and say, I want a picture of a teddy bear...it'll create a black and white outline you can color in like a child." (Paul)
• Recognition that Notepad and Paint are, nonetheless, well-updated and useful apps.

14. Security & Authentication Tips (121:24—130:05)

• Paul walks through best practices for Microsoft account and device security:
  • Use passkeys (password manager/Secure Enclave).
  • Enable Microsoft Authenticator for M365 accounts—most secure and convenient.
  • Proton Authenticator recommended as best all-around free, open-source, fully encrypted option.
  • [124:41] "The very best method is to use a passkey...It's wonderful, but the very best method is to use a passkey...two-step authentication set up passkeys and an authenticator app."
• Richard notes: Microsoft is making 2FA mandatory for all M365 accounts by the end of the year.

15. Local AI: Microsoft’s "AI Dev Studio" Preview (130:05—135:26)

• New developer APIs and Windows app demonstrate local AI capabilities—text/image generation, translation, spell check, image enhancement—using Copilot Plus PCs’ MPUs or CPUs/GPUs.
  • [131:39] "You can see it hitting the MPU and how it's not hitting the CPU, et cetera, et cetera...But this is really, it's not so much a thing you're going to sit there and chat with exactly. It's more of a guide to what is capable right now on any PC."

16. Xbox Segment: Marathon Returns & Game Pass January (99:15—110:10)

• Bungie’s Marathon reboot (from Halo-makers) is forthcoming; excitement over its old-school flavor and gameplay.
• Xbox app improvements for ARM and Game Pass games, including performance-check indicators and cloud save syncing.
  • [105:22] "...goal here is you look at a game and it's like, yeah, this thing's going to work great on your computer or not. Right. I mean, that's actually useful information."
• Rumor: Microsoft may launch a free, ad-supported tier for Xbox Cloud Gaming, mirroring industry trends.

Notable Quotes & Timestamp Highlights

• [04:09] Paul: "This is very typical for our community these days, but it’s got a lot of play, but it didn’t really impact too many people and it’s been fixed."
• [16:13] Paul: "If you don't have enough storage, it will give you an error...everything that's in that folder in the cloud is now going to come to your computer."
• [21:11] Paul: "You should only see the games that are compatible with this computer. That’s how that should work. Right? That’s how stores work."
• [39:03] Richard: "Second-generation bonobos...they've removed all of the bonobos that ever got wet, but the ones that are there still beat the hell out of every newcomer who dares to touch that ladder."
• [67:29] Paul: "They're selling us on this vision where...today requires an astronomical investment that outweighs the profits this company generates every single quarter now. And I'm sorry, I don't see it."
• [73:44] Paul: "I think the bubble needs to burst. I really do. I think the best thing that could happen to us, the number of people I'm talking to right now is like, I can't wait till the bubble bursts so we can get on with it."
• [124:41] Paul: "The very best method is to use a passkey...turn on two step authentication, set up passkeys and an authenticator app."
• [146:49] Richard (on Racia, agave, and moonshine history): "This is the best kind of alcohol. The kind invented to avoid paying taxes."
• [153:13] Richard: "It's one of the reasons it became moonshine, because the upside to the taxation and regulation is consistency and quality. The downside is you cheat."

Memorable Moments

• [11:14] Paul’s everyday carry/self-hosting rant: "It’s a term of tech stupidity of I have got my head so far up my ass that I think my tech out in the Apple watch. It’s everyday carry."
• [46:45] Paul’s bemused take on Paint’s Coloring Book: "You can prompt it and say, I want a picture of a teddy bear. And it will create a black and white outline version of a teddy bear that you can then color in like a child.”
• [39:03] Richard’s bonobo experiment story, to explain organizational tech inertia.
• [73:30] Paul, calling for the AI bubble to burst: "I think the bubble needs to burst. I really do. I think the best thing that could happen to us..."
• [156:17] Richard’s joy in discovering Racia: "This is the simplest, most honest manifestation of agave in a whole area you didn’t know about.”

Liquor Pick: Racia—The Tax-Dodging Spirit of the Mexican Highlands (143:13—156:52)

• Richard delves deep into the roots (pun intended) of Racia, an agave spirit from Jalisco, Mexico, traditionally made "under the radar" to avoid tax collectors, with production only legally recognized in 2014.
• Noted for its botanical "gin-like" character, distinct from the peppery notes of blue agave tequilas.
• “Sometimes I want that, sometimes I don’t. ... I gotta keep this bottle around for the summertime. I want two ice cubes in this and a couple of fingers, and I’m gonna sit on my deck and watch the dolphins do their thing and drink this lovely drink.” (Richard, 155:44)

Final Thoughts

• The episode encapsulates the TWiT ethos: insider expertise, skepticism of corporate tech narratives, historical knowledge, and irreverent fun. The hosts poke fun at insertification, bad design, and the economic priorities now driving Microsoft and Apple—while still recommending good Notepad/Authenticator/Azure features and savoring obscure liquors.
• For users looking to stay abreast of user-impacting Windows news—minus the media panic and plus plenty of context—this episode delivers.

Key Segments & Timestamps

• Boathouse banter: 00:53–03:38
• Windows update kerfuffle: 03:38–08:55
• OneDrive "folder backup" drama: 12:56–19:21
• Xbox on ARM & app curation: 20:13–25:33
• Insertification & AI industry critique: 35:51–77:44
• Linux as a Windows successor: 50:32–56:05
• Security/app picks: 121:24–130:05
• Racia & liquor history: 143:13–156:52