Windows Weekly’s latest episode landed like a double‑barreled jolt: Microsoft quietly flipped the switch on Windows 11 version 25H2 while the Xbox division rewrote Game Pass’s value proposition — and both moves exposed the familiar tension that powers Redmond’s strategy: incremental platform control on the OS side, and aggressive monetization on the consumer services side. The episode’s hosts laid out a week of practical takeaways and headaches for users, IT pros, and gamers alike — from the local account OOBE drama to OpenAI’s expanding platform ambitions and an eyebrow‑raising AMD partnership — and the implications are immediate and far‑reaching.
Microsoft’s autumn playbook is now predictable in cadence but unpredictable in impact: Windows updates arrive as enablement packages that gate‑flip features already staged in servicing, while subscriptions and cloud services are re‑priced or repackaged to chase higher revenue per user. That pattern explains why 25H2 can be both a low‑drama technical rollout and a policy event (because of OOBE behavior and companion app installs), and why Game Pass can be an infrastructure story about new cloud streaming quality and the same week a consumer revolt sparked by a 50% price increase for the Ultimate tier. The Windows Weekly hosts walked listeners through both rails and offered practical tips — including a controversial unsupported‑PC upgrade trick discussed on the show.
What this means in practice:
Practical admin actions:
What to watch:
Why this matters for Windows users and enterprise IT:
Key takeaways for gamers:
What Xbox should do (practical list):
For users and IT pros the immediate prescription is pragmatic: test first, insist on clear communication for end users, and re‑evaluate subscriptions against real usage. For Microsoft the imperative is political as much as technical: preserve trust while extracting more revenue. Those two objectives are easier to list than to reconcile.
Source: Thurrott.com Windows Weekly 953: The Casting of Frank Stallone
Microsoft’s autumn playbook is now predictable in cadence but unpredictable in impact: Windows updates arrive as enablement packages that gate‑flip features already staged in servicing, while subscriptions and cloud services are re‑priced or repackaged to chase higher revenue per user. That pattern explains why 25H2 can be both a low‑drama technical rollout and a policy event (because of OOBE behavior and companion app installs), and why Game Pass can be an infrastructure story about new cloud streaming quality and the same week a consumer revolt sparked by a 50% price increase for the Ultimate tier. The Windows Weekly hosts walked listeners through both rails and offered practical tips — including a controversial unsupported‑PC upgrade trick discussed on the show.Windows 11 25H2: what shipped, what really matters
25H2 is an enablement package, not a rebase
Windows 11 version 25H2 followed Microsoft’s servicing‑first model: it’s largely an enablement package built on the 24H2 servicing branch rather than a full image rebase. That design reduces download size and the surface area for installation regressions — good for fast rollouts and for organizations that want minimal disruption — but it also means feature availability depends on staged server flags and gradual gating. Microsoft’s September 29/30 preview updates (KB5065789, etc.) document the rollout mechanics and the specific fixes included in the September preview.Parity fixes: Notification Center on secondary displays and small wins
One of the most tangible user‑facing fixes packaged for this cycle was restoring Notification Center parity on secondary monitors and re‑introducing an opt‑in seconds clock in the calendar flyout. These annoyances — clicks that had to go back to a primary display — were small but emblematic of the usability drift that initially dogged Windows 11. The update is being delivered as a preview and will be enabled progressively by Microsoft’s server flags, so expect variability across devices even after installing the KB.The local‑account (MSA) drama: fewer escape hatches
A far more consequential change is Microsoft’s tightening of the Out‑Of‑Box Experience (OOBE). Insider Dev/Beta builds have removed previously used bypass methods that let people create local accounts during setup. Known tricks — the “bypassnro” workaround and command‑based local account shortcuts — are being disabled. On those builds, attempting to skip Microsoft account sign‑in can cause OOBE to reset or crash, effectively forcing an MSA sign‑in (or a managed device enrollment) during first boot. Independent reporting confirms the behavior is visible in recent Insider drops and appears aimed at reducing partial OOBE states that can break telemetry, updates, or companion app flows. This is a design choice: Microsoft wants a consistent, cloud‑connected baseline at first sign‑in, and the company is now leaning on the OOBE to enforce it.What this means in practice:
- Home users may have fewer frictionless options to avoid a Microsoft account unless they use image‑based unattended installs or enterprise provisioning tools.
- IT teams and privacy‑conscious users should test unattended deployment workflows (Answer File/Autounattend.xml or enterprise provisioning) to avoid user friction.
- The enforcement could create real support volume for help desks if consumers are surprised or if activation/telemetry flows break due to intermittent connectivity during setup.
OneDrive, Companion apps, and forced installs: creeping surface area
Windows Weekly flagged coming OneDrive client improvements and the broader push to preinstall Microsoft 365 Companion apps on Windows 11 devices. Microsoft has been experimenting with companion app auto‑installs and tighter Copilot integrations; those moves centralize experiences but raise governance and privacy questions for admins. The hosts suggested admins review Intune and group policy controls to manage companion app behavior and to keep an eye on the Microsoft Release Health dashboard for updates.Practical admin actions:
- Audit device configuration policies and consent frameworks.
- Test companion app auto‑install behavior in pilot rings.
- Prepare comms for users to explain why certain cloud services are now part of the default experience.
OpenAI, ChatGPT as a platform, and the AMD deal
ChatGPT becomes an app platform — and that changes the calculus
OpenAI’s recent launch of an Apps SDK means ChatGPT is shifting from an assistant to a platform: third‑party services (Booking.com, Canva, Coursera, Expedia, Spotify, Zillow and others in pilot) can now embed interactive apps directly into ChatGPT conversations. The platform approach uses the Model Context Protocol (MCP) and is rolling out outside the EU initially, with SDK previews available to developers. The implications are profound: ChatGPT can now suggest and invoke apps contextually during conversation, handling tasks like booking trips, creating playlists, or generating design files without the user leaving the chat. This turns ChatGPT into a conversational app ecosystem — and one that will compete for commerce and data flows previously siloed by mobile app stores and web services.What to watch:
- How OpenAI monetizes app integrations and what revenue splits or data‑sharing terms it requires.
- Privacy and consent flows: apps must ask before connecting accounts or sharing data, but default UX patterns matter.
- Competitive responses from Google, Apple, and others who see a potential new axis of app distribution.
OpenAI + AMD: compute diversification at scale
In a major infrastructure move, OpenAI and AMD announced a multi‑year agreement for large‑scale AMD GPU deployments — a six‑gigawatt commitment with an initial 1‑gigawatt MI450 deployment slated for the second half of 2026. AMD’s public press materials describe warrants and milestone‑based vesting tied to deployments; OpenAI’s multi‑vendor compute strategy reflects the industry’s need to diversify supply beyond a single dominant supplier. The deal is material for both companies: OpenAI secures additional hardware supply while AMD gains a potential multi‑billion‑dollar committed customer.Why this matters for Windows users and enterprise IT:
- Cloud AI services — including those integrated into Windows and Microsoft 365 — may increasingly run on heterogeneous GPU backends, changing performance and availability dynamics.
- Enterprises planning on-prem or hybrid AI infra should expect the market to evolve rapidly as hyperscalers and AI firms make large procurement bets.
Perplexity Comet and the rise of AI‑first browsers
Perplexity’s Comet AI browser has moved from a paid product tier to a broadly free offering with usage limits, opening access to a sidebar chat and web‑augmented answers inside a browser shell. Perplexity framed this as a mass‑market play: AI‑augmented browsing with a built‑in assistant that can summarize, extract, or act on pages. Expect a proliferation of agentic browsers, and with it, new privacy and security considerations where the browser is capable of taking actions on a user’s behalf.Xbox and gaming: the Game Pass earthquake
The price shock and the hard pivot to premiumization
Microsoft restructured Xbox Game Pass into three named tiers — Essential, Premium, and Ultimate — and raised the price of Game Pass Ultimate from $19.99 to $29.99 per month in key markets while increasing PC Game Pass pricing as well. Microsoft simultaneously promised substantial library expansion, more than 75 day‑one releases per year in the Ultimate tier, higher quality cloud streaming (up to 1440p), and added partner bundles like Ubisoft+ Classics and Fortnite Crew for Ultimate members. Xbox Wire framed the move as a value upgrade for heavy players.Consumer reaction and Microsoft’s partial backstep
The immediate reaction was predictably negative: steep price increases for a top tier prompted cancellations, complaints on social media, and a sharp debate about subscription economics. Microsoft later clarified that the new prices would not immediately affect existing subscribers in some countries and that local regulatory requirements constrain how quickly price changes can be applied in certain markets. That clarification — effectively a partial delay or “not right now” for some regions and for auto‑renewing customers — eased some backlash but did not erase the strategic pivot.Key takeaways for gamers:
- Heavy players who use day‑one releases and cloud streaming may still find Ultimate compelling despite the higher price.
- Casual players will probably migrate to Premium or Essential or consider ownership for the few games they actually play.
- Families and multi‑platform households need to run the math — the new Ultimate pricing is no longer an automatic win.
Hardware rumors and Microsoft’s response
Circulating rumors that Microsoft would abandon Xbox hardware in favor of a pure cloud/publishing play were publicly denied. Microsoft reiterated continued investment in Xbox hardware and pointed to AMD partnerships to underline that hardware plans remain in play. The company’s messaging aims to reassure a base already skittish after repeated price increases and changes in strategy.How bad is it? What Xbox should do
The Game Pass pricing reboot is a classic product‑market mismatch risk: Microsoft is trying to fund expensive day‑one release economics and cloud investment by extracting more revenue per heavy user, but the optics of a 50% price increase for many former loyal subscribers are poor.What Xbox should do (practical list):
- Offer a clear grandfathering policy and predictable timelines for existing subscribers.
- Introduce a family/friends plan that matches the economics of multi‑player households.
- Improve transparency on day‑one content cadence and commit to a minimum annual roster to justify the premium.
- Expand regional pricing sensitivity — what’s acceptable in one market is untenable in another.
Gaming hardware and handhelds: Windows as a mobile gaming platform (but not quite yet)
Handheld Windows devices like the Lenovo Legion Go 2 showcase what Windows can be as a mobile gaming platform: high refresh OLED panels, zippy AMD Z2/Z2 Extreme silicon, detachable controllers, and a PC‑grade library. Hands‑on reviews praise the screen and performance but consistently call out battery life, price, and Windows 11’s suboptimal handheld UX as limiting factors. Windows can be a mobile gaming platform; it’s just not perfect yet. The Legion Go 2’s hardware design is impressive, but the operating system and software ecosystem remain the Achilles’ heel.Legal and market context: Epic v. Google
Outside Microsoft’s fences, the broader platform economy is also shifting. The Ninth Circuit recently upheld remedies requiring Google to open parts of the Play Store to competition after Epic Games’ antitrust win — a ruling that compels Google to permit rival app stores and alternative billing methods. That decision is likely to reshape Android distribution and has major implications for app store economics worldwide. The ruling also underscores the strategic value of platform control: companies that control distribution can extract commission economics that subsidize other parts of their businesses.Tips and picks from the show — actionable items for readers
- Tip of the week: the hosts discussed an unsupported upgrade trick: running the 25H2 ISO’s setup.exe from a mounted D: drive with a product switch (D:\setup.exe /product server) to upgrade unsupported Windows 10 or 11 machines. This is a community‑level workaround and should be treated with caution: unsupported hardware upgrades can create driver, activation, or security issues. Do this only after full backups and in test environments.
- App pick: Opera Neon (as discussed on the show) — touted as an agentic AI browser that is currently paid but noteworthy as a trusted AI browser in early access. Note: readers should evaluate privacy and security policies before paying for agentic browsing features.
- Brown liquor pick: Weller 12 — the hosts’ lighter cultural touchpoint was included to close the week’s episode notes.
Critical analysis: strengths, risks, and what to watch next
Strengths — platform leverage and product bundling
Microsoft’s moves illustrate a disciplined platform playbook:- Windows: incremental, low‑risk enablement packages allow Microsoft to push features with less disruption and maintain enterprise manageability.
- Xbox/Game Pass: bundling, higher cloud quality, and partner inclusions (Ubisoft+ Classics, Fortnite Crew) create a more defensible premium product for heavy users.
- OpenAI: turning ChatGPT into a platform is a textbook network effect play; apps inside ChatGPT accelerate daily utility and lock‑in.
Risks — trust, churn, and regulatory friction
But there are real hazards:- Trust erosion: forcing Microsoft account sign‑ins and auto‑installing companion apps increases friction and will feed privacy/choice backlash.
- Subscription fatigue and churn: a 50% price hike for the flagship gaming subscription won’t scale if churn outpaces the added revenue per surviving user.
- Regulatory exposure: platform control and bundling attract antitrust scrutiny — the Epic v. Google example shows the stakes for dominant distributors. Microsoft must navigate that landscape as it consolidates services and embeds AI across Windows and cloud.
Operational guidance (for admins and advanced users)
- Test 25H2 in a controlled pilot ring. Verify Arm64 imaging and Media Creation Tool workflows; Microsoft’s staged flags mean not all devices get the same features immediately.
- Update deployment docs to account for companion app auto‑installs and Copilot changes. Prepare an opt‑out or removal plan for sensitive fleets.
- For gamers: reassess Game Pass usage — model annual costs, day‑one value, and whether multi‑user households can consolidate with family‑level discounts (if/when introduced).
Conclusion
This week’s conversation captured a microcosm of modern platform strategy: minimal‑drama technical updates that quietly reshape user expectations, paired with bold subscription economics that test consumer tolerance for premium pricing. Microsoft’s twin moves — pushing for a cloud‑connected baseline in Windows and re‑pricing Game Pass into a premium tier — are internally consistent but externally risky. OpenAI’s platform pivot and its strategic AMD compute linkage highlight how compute, distribution, and monetization are now inseparable in the AI era.For users and IT pros the immediate prescription is pragmatic: test first, insist on clear communication for end users, and re‑evaluate subscriptions against real usage. For Microsoft the imperative is political as much as technical: preserve trust while extracting more revenue. Those two objectives are easier to list than to reconcile.
Source: Thurrott.com Windows Weekly 953: The Casting of Frank Stallone