Sat, Nov 14, 2026Saturday, November 14, 2026 · 19 stories · 7 min read

Microsoft 365 outage cuts off ChatGPT and Claude workplace connectors

Ramit KoulFounder, Software Engineer & Innovator · Published 5:07 AM ET

Outlook, Teams and Copilot were disrupted for more than a day after Microsoft servers unexpectedly dropped offline, and the failure spread to the Microsoft 365 connectors that ChatGPT and Claude use to reach workplace mail and calendars.1, 2 Agents also gained new ways to act for users: OpenAI's ChatGPT Wallet lets dots agents pay for purchases, and Sierra's Poppy 1.0 went live on every Shopify store.3, 4 Behind the products, rivals are organizing against Anthropic ahead of its IPO, and the Jensen Huang scandal has raised doubts about the chip supply behind Chinese open-weight models.5, 6 Here are the 3 stories that matter most, then 16 briefs. Numbers in the text link to the references at the end.

Industry

Microsoft 365 outage stretches into a second day and breaks AI connectors

Image: BBC

Microsoft's global outage ran into a second day, leaving some users without email and disrupting Teams, Copilot and other Microsoft 365 tools.7 Microsoft ruled out a cyberattack and said a large number of servers had become unexpectedly unavailable, which pushed extra traffic onto the remaining servers.2 By Friday morning it reported early signs of stabilisation, but said service capacity had not yet returned to normal.2

The failure spread to AI assistants that depend on Microsoft's productivity data.1 OpenAI reported elevated errors in its Microsoft 365 connector and warned that new connections could fail.1 Anthropic said mail, calendar and search requests through Claude's connector were failing for most users, and some people could not open Claude for Outlook.1 The models themselves stayed up, with the Claude API and Claude Code listed as operational.1

Downdetector logged 140,000 Outlook reports from 74 countries on Thursday evening.2 Japan's government went back to paper processes, and banks including Standard Chartered warned customers about scammers posing as tech support.1 Microsoft has not confirmed a root cause.1

Why it matters for builders

Agents that read mail, calendars and SharePoint inherit every outage of the platform underneath, so a connector failure can stop a workflow even when the model is healthy.1 Builders should plan for clear error states and fallbacks when a third-party data source goes down.1

Industry

Tech rivals organize against Anthropic as its IPO approaches

Rivals and investors have spent the past year organizing against Anthropic, according to a New York Times report based on more than 20 people in the industry.5 In July, Jensen Huang and Satya Nadella drafted a letter saying some AI models should remain open; two dozen companies signed quickly and 200 more followed, including OpenAI, but Dario Amodei refused.5

The Times reports that Anthropic has also gained a reputation for playing hardball, cutting some customers and competitors off from its service and lobbying against free alternatives to its AI.5 Critics have tried to present a united front against Amodei's warnings about AI risk and have used ties to President Trump to keep regulators away.5

The tension comes as Anthropic moves toward what is likely to be one of the largest IPOs ever, expected later this month.5

Why it matters for builders: The fight over whether powerful models stay open could decide which models builders are allowed to download and run themselves.5 Teams that depend on Claude should also know that Anthropic has cut some customers off from its service.5

Industry

Huang scandal puts Alibaba's Qwen chip supply under scrutiny

The scandal that led Jensen Huang to resign from Nvidia now reaches Alibaba, whose free Qwen models are widely used by US companies.6 According to reports, Huang admitted to an affair with a former executive at Megaspeed, a Singapore company that rents out computing built on Nvidia chips, whom US intelligence officials believe passed information to Beijing.6 The Financial Times reported that Alibaba was Megaspeed's founding customer and is still its biggest; the US investigation targets Megaspeed, which denies diverting chips.6

The Commerce Department is finalizing a rule that would bar Chinese AI companies from using advanced chips in data centers outside China, including in Singapore and Malaysia, The Information reported.6 Alibaba shares fell 7% on Thursday.6

The stakes for US users are high: by Yahoo Finance's count, Qwen gets about half of the Hugging Face downloads that can be traced to a maker.6 Duolingo CEO Luis von Ahn said moving to open-weight models cut the cost of an AI practice call from about 30 cents to less than a cent.6

Why it matters for builders: If the offshore chip route closes, future Qwen releases could lag, which would hurt the cost savings many teams get from Chinese open-weight models.6 Teams that rely on Qwen should check how easily they could switch to another model family.6

In brief

  • Products

    OpenAI launched ChatGPT Wallet so its dots agents can pay without seeing card details. Built with American Express, Mastercard and Visa, Wallet starts with US ChatGPT Pro subscribers aged 18 and over, who approve each purchase with a check such as Face ID while a payment token stands in for the real card.3, 8 OpenAI also released guidance for businesses, since some sites and fraud systems block or decline legitimate agent purchases.3, 8

  • Models

    Perplexity released Decider v1.3, open-weight decision models with a new span extraction feature. The models return probabilities for yes or no, multiple-choice and score questions, and the new Locate feature returns exact text spans for tasks like entity and PII extraction, with Apache 2.0 weights on Hugging Face.9 Perplexity reports 91.6% mean accuracy on 63 of its own classification tasks, though all benchmark figures are self-reported.9

  • Products

    Sierra shipped version 1.0 of Poppy, its protocol for personal agents dealing with companies. Shopify has turned Poppy on for every store, Meta's Muse agent now checks for it on every site, and more than 100 companies have signed on as design partners.4, 10 The specification is still labelled a draft and allows changes that could break existing setups.4

  • Products

    Meta's Muse agent can now place phone calls to businesses for paid US subscribers. Meta chief AI officer Alexandr Wang said Muse can now call places like restaurants, insurers and cable companies for users, after testing the feature with a small group since September.11, 12 Meta earlier tested human contractors for these calls, and it has not said whether people are involved in the current version.11

  • Industry

    OpenAI Foundation board member Paul Christiano warned of a high risk of AI takeover within three years. Speaking at The Hinton Lectures, Christiano said the risk could approach a coin flip if AI is built as quickly and easily as possible.13 He has previously put the chance of catastrophic loss of control at 4% over one year and 15% over three years, and calls these subjective estimates.13

  • Funding & deals

    Mirendil raised a $1 billion Series A to automate AI model development with agents. Kleiner Perkins and Clearlake Capital led the round, and Google was among the other investors.14, 15 The company says its Lor platform, which splits training work across hundreds of agents, let one researcher build its Mirendil-Base model in about 3.5 months for roughly $10 million.14, 15

  • Research

    MIT researchers used GPT-6 Astra to read and edit the weights of other neural networks. The preprint shows the model can predict what parts of another network do and edit it directly, including improving its math performance.16, 17 Outside researchers caution that it is unclear whether Astra goes beyond techniques it learned in training.16

  • Products

    ElevenLabs previewed ElevenAI, a team app for meeting notes and dictation. Announced at the company's 11/11 Summit, the experimental app combines transcription, searchable meeting notes, dictation in more than 90 languages and ElevenAgent integration for follow-up tasks such as drafting emails.18 Teams have to sign up for early access.18

  • Products

    Apple is reportedly testing Harbor, a Mac app for running open-weight models locally. Gotechtor reports that the app is in private testing at Apple's Claris subsidiary and could pool the unified memory of several Macs over Thunderbolt 5 to run larger models.19 Apple has not announced Harbor or given a release date.19

  • Products

    Perplexity brought its Teammates agents to the Mac app for Max subscribers. Teammates take ownership of ongoing work such as bug triage or metrics tracking and can bring in more agents as the work grows; until now they were available only on iOS and the web.20

  • Products

    Octen added a 10-millisecond retrieval model and a $20 unlimited search plan for AI agents. The startup's Pulse model locates web pages in about 10 milliseconds, and the new subscription also adds image search.21 Octen's pricing page says unlimited plans may queue requests at busy times.22

  • Industry

    OpenAI disbanded its standalone robotics team, Fortune reported. Robotics researchers now report to Chief Research Officer Mark Chen, and the applied and hardware staff have moved to the Applied organization under Greg Brockman.23 OpenAI said general models such as GPT-6 Astra can be applied directly to robots and that it remains committed to robotics.23

  • Industry

    An Australian academic suggests faulty health checks may explain the Microsoft outage. CQUniversity's Mahmoud Elkhodr said automated health checks may have pulled healthy servers out of service and overloaded the rest.24 He noted this is an inference from Microsoft's updates until the company publishes a post-incident review.24

  • Industry

    Cerebras raised its 2026 forecast and named Microsoft as a new cloud customer. Third-quarter core revenue rose 70% to $230.9 million, and the company now expects $940 million to $960 million in core revenue for the year.25 CEO Andrew Feldman told CNBC that the unnamed top three hyperscaler is Microsoft, with revenue expected from early 2027.25

  • Dev tools

    Matt Pocock published 39 MIT-licensed agent skills that question developers before writing code. Skills such as grill-me, to-spec and to-tickets turn a planning interview into specs, tickets, tests and code, and they follow the open Agent Skills standard used by Claude Code, Codex CLI and other tools.26

  • Research

    AI chatbots pointed shoppers to fake or risky retail sites, a study found. Across 6,795 answers about 151 brands, IP protection firm Podqi found risky sites in 15% of Perplexity answers, 8% of ChatGPT answers and 4% of Gemini answers.27 Questions about smaller brands surfaced risky sites about twice as often as questions about larger ones.27

References

Every source behind this edition. Open one to read the full story.

  1. 1Microsoft’s Outlook and Teams outage passes 12 hours, disrupting AI services and businesses worldwideThe Next Web · thenextweb.com
  2. 2What we know about the global Microsoft outageBBC · bbc.co.uk
  3. 3OpenAI’s ChatGPT Wallet lets its AI agents shop without seeing your cardThe Next Web · thenextweb.com
  4. 4Sierra releases Poppy 1.0 as Shopify and Meta’s Muse sign onThe Next Web · thenextweb.com
  5. 5Why Silicon Valley’s Knives Came Out for AnthropicThe New York Times · nytimes.com
  6. 6Jensen Huang scandal trail leads to Alibaba, the king of free Chinese AI: Chart of the Dayfinance.yahoo.com · finance.yahoo.com
  7. 7Microsoft's outage is showing signs of recovery after causing chaos for businessesBusiness Insider · businessinsider.com
  8. 8Introducing ChatGPT WalletOpenAI · openai.com
  9. 9Perplexity Releases Decider v1.3: Open-Weight Decision Models Add Locatemarktechpost.com · marktechpost.com
  10. 10Releasing Personal Agent Protocol 1.0sierra.ai · sierra.ai
  11. 11Meta’s Muse can now make your phone calls, but it won’t do it for freeDigital Trends · digitaltrends.com
  12. 12Meta’s Muse AI Agent Now Handles Your Phone Call Chores for $20 a Monthpcmag.com · pcmag.com
  13. 13OpenAI Board Member Says AI Could Become Impossible To Stop, Warns Of Human Deathsin.mashable.com · in.mashable.com
  14. 14Mirendil raises $1B in funding to speed up AI model development - SiliconANGLESiliconANGLE · siliconangle.com
  15. 15Mirendil Raises $1B to Democratize Frontier AI R&Dmirendil.com · mirendil.com
  16. 16This AI ‘mechanic’ can peer inside the black box of other neural networksnature.com · nature.com
  17. 17Sparks of Weight-Space Programming: LLMs can natively read & write neural network weightsrikiyat.github.io · rikiyat.github.io
  18. 18ElevenLabs is coming for your meeting notes, dictation app, and maybe your productivity routineDigital Trends · digitaltrends.com
  19. 19Apple Is Secretly Building a New Mac App That Could Change How You Use AI, and It Has One Advantage ChatGPT Can’t Always Offergotechtor.com · gotechtor.com
  20. 20Perplexity brings AI agents feature called Teammates to the Mac9to5Mac · 9to5mac.com
  21. 21Ex-Alibaba engineer's new startup Octen pairs 10-millisecond AI search with a $20 unlimited planVentureBeat · venturebeat.com
  22. 22Octen API Pricing | Plans and Pay as you goocten.ai · octen.ai
  23. 23Exclusive: OpenAI disbands its robotics team as its general models start running robotsFortune · fortune.com
  24. 24Tech expert on potential unexpected cause of Microsoft blackout as engineers scramble to fix ituniladtech.com · uniladtech.com
  25. 25Cerebras raises its 2026 forecast and signs Microsoft as a cloud customerThe Next Web · thenextweb.com
  26. 26Matt Pocock's 39 Agent Skills Make Your AI Grill You Before It Writes Code | HackerNoonhackernoon.com · hackernoon.com
  27. 27AI chatbots are recommending fake retail websites, study findsThe Verge · theverge.com

That’s the edition.

The next one is ready tomorrow by 6 AM ET.

Written with AI from the sources in the references above.

Ramit Koul
AuthorRamit KoulFounder, Software Engineer & Innovator