WW 956: Blowing the Dust Off Skype - Azure's Front Door Leaves Customers Locked Out

Oct 29, 2025

Microsoft experienced a significant Azure outage on earnings day, leading to widespread service disruptions. In the fast-paced AI landscape, they discussed practical ways to evaluate AI effectiveness. Windows 11's preview update brought exciting new features like a revamped Start menu and improved voice access. Meanwhile, a lawsuit over misleading Microsoft 365 pricing highlights ongoing transparency issues. Plus, the podcast touched on Grammarly's rebranding and insights on Xbox's hardware strategy.

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INSIGHT

Cloud's Fragile Single Point Of Failure

Cloud outages expose fragile dependencies: many Microsoft services and sign-in flows rely on Azure and Front Door.
Paul and Richard highlight that DNS, human error, and single-point front-door failures cause cascading outages.

ANECDOTE

Locked Out By Authenticator Loop

Paul and Richard describe being locked out of Microsoft services because Authenticator and Azure were down.
They recount the frustrating circular sign-in loop and inability to access Loop, Teams, and Loop notes.

INSIGHT

Features Downloaded But Locked By Cloud Flags

Windows feature rollout is decoupled from download: same cumulative KB can target multiple OS versions but enable features later.
Controlled feature releases mean identical systems can have different features enabled at random times.

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Welp, Azure crashed on Microsoft's earnings day, the cloud's weakest link exposed just as AI investments hit mind-boggling numbers. And 2.5 years into the AI era, things are still moving quickly, and there are extreme opinions on both ends of the spectrum. But Paul finally found a source for a good way to evaluate AI and figure out where it works and where it does not. It came from an unexpected place.

Windows 11

Week D arrives with a massive Preview Update for 24H2 and 25H2 - including the new Start menu, finally
Copy & Search, Voice typing improvements, Proactive Memory Diagnostics, more in Dev and Beta
Copilot Vision in Copilot app updated with text input and output across all Insider channels
Intel earnings are great unless you understand how numbers work

Microsoft 365

Australia regulator sues Microsoft over misleading Microsoft 365 consumer pricing
Copilot is being integrated into the People, Files, and Calendar companion apps for Microsoft 365 commercial
On the day Microsoft will report earnings, Microsoft 365 and Azure went down. Hilarious!

OpenAI completes its transition to a for-profit owned by a non-profit
Microsoft's stake is 27 percent. A lot has changed in the Microsoft/OpenAI partnership agreement
WSJ finally calls out Microsoft for its lack of financial reporting transparency. Paul's been complaining about that for over a decade - Big Tech has became a shell game. These companies are managing money they don't even have and actual products and services and "real" value be damned
Big Copilot feature dump for consumers with a human touch: Mico, Copilot Groups, memory improvements, connectors, Proactive Actions in preview, Copilot for Health, Copilot in Edge improvements, and Copilot in Windows updates from last week
Microsoft 365 Copilot is getting App Builder and Workflow agents
GitHub Copilot to support third-party AI agents
Grammarly rebrands as Superhuman

Xbox and gaming

Credible report claims Microsoft requires Xbox/Microsoft Gaming to deliver 30 percent profit margin
That is impossible and this is clearly coming from Amy Hood and has led to the ensh*ttification of Xbox as a platform
As Microsoft launches first gaming handhelds, all anyone wants to talk about is the next-generation Xbox console. It started with Sarah Bond last week - "very premium" console with "curated" experience
Phil Spencer discusses it this week, who implied Windows at the heart of console
The rumor mill churns up - Will be Windows, as we've said, will drop multiplayer paywall that debuted in 2002
Now Satya Nadella is commenting on the next console, confirms publisher focus for this business
Halo: Campaign Evolved is coming in 2026, new features, new Unreal Engine graphics, new PS5 compatibility
Also, The Outer Worlds 2 is now available. Yes, on PS5 too
Amazon relaunches Luna, and the new Amazon layoffs point to a new focus on casual gaming

Tips and picks

Tip of the week: Understand where AI works and where AI is just a marketing term used to hype something that doesn't work
App pick of the week: Tiny11 Builder
RunAs Radio this week: AI for DBAs with Grant Fritchey
Brown liquor pick of the week: Redbreast Dream Casks

These show notes have been truncated due to length. For the full show notes, visit https://twit.tv/shows/windows-weekly/episodes/956

Hosts: Leo Laporte, Paul Thurrott, and Richard Campbell

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