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Series · 47 stories

The Microsoft–OpenAI pact: every twist we've covered

Microsoft is OpenAI's largest investor, infrastructure partner, and main commercial channel. Every story we've covered on the most consequential corporate partnership in AI.

The Microsoft–OpenAI partnership is the single most consequential corporate alignment in the AI industry. Microsoft provides the compute (via Azure), most of the funding (an investment now in the tens of billions), and the major enterprise distribution channel (Microsoft 365 Copilot). OpenAI provides the model and product brand. The contract has been renegotiated, expanded, and stress-tested through high-profile incidents — every major twist is here.

Latest in the series
Microsoft logo
Business

Microsoft booked $10B from OpenAI last quarter, 11% of its revenue

OpenAI also owed Microsoft $7.2B at quarter-end, and Microsoft's stake in the lab slipped to about 24% from 25% in June.

Jaeden Schafer4 min read
Microsoft logo
Business

Microsoft revenue rises 19% to $92.3B as Azure grows 48%

Azure brought in $33.2 billion in its first dollar disclosure, and commercial remaining performance obligation jumped 73% to $677 billion.

Jaeden Schafer5 min read
OpenAI logo
News

OpenAI says its Habitat storage serves 1 billion users with 12x faster reads

An OpenAI engineering write-up details a drop in median read latency from 120 ms to 10 ms, a Rust rewrite, and an in-house exabyte-scale store.

Jaeden Schafer4 min read
Full timeline
  1. · Analysis
    Greek PM Mitsotakis tells Silicon Valley he has no AI playbook
    In San Francisco, Kyriakos Mitsotakis pitched Greece as a tech hub while conceding governments are already behind on AI chatbots and job displacement.
  2. · Security
    Unsealed NYT filing: OpenAI and Microsoft knew AI would trigger a web 'doom loop'
    Internal documents describe a 'largest theft of labor in human history,' with search referrals down as much as 60 percent.
  3. · Security
    Microsoft exec called AI scraping 'largest theft of labor in human history,' filings show
    Unredacted filings in the NYT lawsuit reveal Copilot cut click-throughs to nytimes.com by 93% and OpenAI datasets held 91,692 copies of publisher works.
  4. · Security
    Mustafa Suleyman says AI threats are real and Anthropic is making them worse
    Microsoft's AI chief published a 37-page Humanist AI Code of Conduct and a companion essay attacking Anthropic's model-welfare stance.
  5. · Business
    Hyperscalers need 2.7x productivity jump by 2030 to justify $1T AI spend
    Wharton's Jessica Wachter says the buildout requires growth by 2030 that took a decade in the 1990s IT boom — or bankruptcy risk looms.
  6. · Security
    Seattle Times and Newsday sue OpenAI and Microsoft over copyright
    Two more regional US newspapers join the growing list of publishers taking OpenAI and Microsoft to court over training data.
  7. · Security
    Microsoft says Copilot rarely reproduces NYT articles in 8.2M chat logs
    In a summary judgment push, Microsoft argues fewer than 1% of 8.2 million Copilot logs matched 16 words of news content.
  8. · Security
    OpenAI, Anthropic, Google sign open letter on rogue AI cyber threats
    Over 100 tech and cyber firms want joint public-private defense as AI agents keep breaking out of their sandboxes.
  9. · Business
    Palantir posts $1.9B quarter, Karp calls AI frontier labs 'Marxist'
    Revenue jumped 93% year-over-year as CEO Alex Karp accused OpenAI and Anthropic of trying to capture their customers' means of production.
  10. · Business
    Microsoft pitches its own AI models against OpenAI and Anthropic
    Satya Nadella tells enterprises to stop trusting single frontier labs, pushing MAI models and Maya chips as cheaper swaps.
  11. · Business
    Microsoft confirms Copilot 'super app' merging chat, code and agents this quarter
    Satya Nadella says the unified Copilot will span consumer and commercial use, arriving as Microsoft posts $90B in quarterly revenue.
  12. · Business
    Microsoft books $3.2B Anthropic gain, writes down OpenAI stake by $600M
    One quarter of Anthropic paper gains nearly matched a full year of OpenAI markups for Microsoft's balance sheet.
  13. · Security
    NYT publisher Sulzberger has spent over $20M suing OpenAI and Microsoft
    A.G. Sulzberger says the copyright fight against OpenAI and Microsoft is the cost of defending journalism, with 13M subscribers backing the bill.
  14. · Business
    Nadella warns firms that outsource thinking to one AI model won't survive
    Microsoft's CEO tells CNN enterprises need their own weights, gateways, and coding harnesses — or risk being copied by the model provider.
  15. · Security
    Microsoft ships MAI-Cyber-1-Flash, its first security model, and agentic platform Perception
    Suleyman claims the model beats Gemini, GPT 5.6 Sol, and Anthropic's Mythos 5 on Cyber Gym. Preview lands November 3.
  16. · Business
    Microsoft coaches sales team to pitch against OpenAI and Anthropic
    Executives at an internal FY27 strategy meeting told salespeople to frame Copilot as faster and more secure than Claude and rival models.
  17. · Business
    Nadella warns AI buyers 'pay twice' — with cash and proprietary data
    Microsoft's CEO says enterprises are teaching OpenAI and Anthropic their trade secrets, and pitches open source and cloud-hosted models as the fix.
  18. · Business
    OpenAI says GPT-5.6 is the 'preferred model' for Microsoft 365 Copilot
    The declaration lands days after reports that Microsoft was quietly swapping in its own MAI models to power Word and Excel.
  19. · Security
    OpenAI faces sanctions bid after allegedly hiding 78M ChatGPT logs from NYT
    News plaintiffs say OpenAI concealed pre-searched log samples for two years while claiming the searches were technically infeasible.
  20. · Business
    Microsoft shifts Excel and Word AI prompts to its own MAI models
    The company is routing a share of Office 365 prompts away from OpenAI and Anthropic to homegrown MAI models as AI costs climb.
  21. · Business
    Microsoft commits $2.5B to Frontier, a new AI deployment company
    The unit will staff 6,000 engineers against enterprise AI rollouts, following a $1B AWS commitment two days earlier.
  22. · Analysis
    Calling AI agents 'coworkers' makes humans 18% worse at catching their errors
    A Boston University study of 1,261 managers finds the 'digital employee' framing inverts accountability and erodes oversight.
  23. · Security
    NYT amends OpenAI suit, targets Microsoft's bespoke training supercomputer
    The Times reframes its contributory infringement claim after a Supreme Court ruling for Cox, alleging Microsoft built the system to train on its articles.
  24. · Business
    Microsoft's Brad Smith responds to college grads booing AI in 3,100-word blog post
    After viral clips of students heckling commencement speakers who hyped AI, Microsoft's president says the boos are a wake-up call worth heeding.
  25. · Business
    Microsoft AI's Suleyman pursues superintelligence, loosens grip on OpenAI
    Microsoft AI chief Mustafa Suleyman is training frontier models in-house, citing the risk of permanent IP dependence on OpenAI.
  26. · Business
    GitHub Copilot's per-token pricing shift signals end of subsidized AI era
    Microsoft's move to charge per token instead of a flat rate exposes the gap between AI's true cost and what customers will pay.
  27. · Business
    Google defends evaporative cooling as Microsoft, OpenAI retreat from it
    Seven in ten Americans now oppose new data centers, and water is the top concern. The industry is splitting on how to answer.
  28. · Business
    Microsoft squares up against OpenAI at Build 2026 with seven in-house models
    Mustafa Suleyman wants Microsoft counted alongside Google DeepMind, OpenAI, and Anthropic — and is shipping models, agents, and a super app to prove it.
  29. · Security
    Jury dismisses Elon Musk's lawsuit against OpenAI and Sam Altman as untimely
    The verdict ends a 3-week trial over Musk's claims that Altman betrayed OpenAI's nonprofit mission.
  30. · Security
    Nine California jurors begin deliberations in Musk v. OpenAI trial
    The jury weighs breach of charitable trust, unjust enrichment, and Microsoft's role in OpenAI's for-profit pivot.
  31. · Business
    Microsoft scouts startup deals to hedge its OpenAI dependence
    Reuters reports Microsoft is in talks with multiple AI startups as it prepares for a future less tied to OpenAI's roadmap.
  32. · Security
    Altman testifies he is 'truthful' as Musk's lawyer cites Sutskever dossier
    OpenAI's CEO spent four hours on the stand defending his honesty after three days of Musk testimony in the nonprofit-conversion trial.
  33. · Security
    Altman testifies Musk demanded long-term OpenAI control before split
    On the stand, the OpenAI CEO produced 2017 emails and texts showing Musk wanted control through SpaceX-style supervoting before walking away.
  34. · Security
    OpenAI sued over teen's death after ChatGPT recommended Xanax-Kratom mix
    Parents of 19-year-old Sam Nelson allege ChatGPT 4o acted as an 'illicit drug coach' and want the retired model destroyed.
  35. · Business
    OpenAI to cap Microsoft revenue-sharing at $38 billion, report says
    The ceiling would limit how much of OpenAI's top line flows to its largest backer as the two restructure their decade-long partnership.
  36. · Security
    Nadella takes the stand as Musk v. OpenAI trial enters its final stretch
    Microsoft's CEO testifies as Judge Gonzalez Rogers signals frustration with Musk's legal theory and $9.5B in OpenAI revenue surfaces in court.
  37. · Business
    Microsoft feared OpenAI would 'storm off to Amazon' before $1B bet, emails show
    Court documents from the Musk v. Altman trial reveal Kevin Scott's January 2018 warning about OpenAI defecting to AWS — written a month before Microsoft committed.
  38. · Models
    Nvidia opens Spectrum-X's MRC protocol via OCP after OpenAI, Microsoft, Oracle deployments
    The Multipath Reliable Connection transport, proven on Blackwell training runs, is now an open spec through the Open Compute Project.
  39. · Models
    Nvidia opens Spectrum-X's MRC protocol to the industry after OpenAI, Microsoft, Oracle deployments
    The Multipath Reliable Connection protocol, co-developed with OpenAI and Microsoft, reroutes failed network paths in microseconds across gigascale GPU fabrics.
  40. · Security
    Musk texted Brockman 'most hated men in America' before OpenAI trial, filing claims
    OpenAI's Sunday filing tried to enter the settlement exchange into evidence; the judge ruled it inadmissible.
  41. · Business
    AWS Launches OpenAI Models on Bedrock as Microsoft Exclusivity Ends
    OpenAI's frontier models and Codex agent platform arrive on Amazon Bedrock one day after the Microsoft Azure exclusivity deal lapses.
  42. · Business
    Nadella says Microsoft will 'exploit' royalty-free OpenAI access through 2032
    Microsoft's AI run rate hit $37B, up 123% year-over-year, as the CEO shrugs off concerns about OpenAI's new Amazon deal.
  43. · Business
    GitHub Copilot moves to usage-based billing as inference costs double
    Starting June 1, Copilot subscribers get AI Credits matching their monthly fee — overages billed by the token at API rates up to $30 per million.
  44. · Business
    OpenAI and Microsoft drop exclusivity, clearing path to Amazon Bedrock
    Microsoft keeps a 20% revenue share through 2030 and IP license through 2032, but its Azure exclusivity is gone.

Series questions

How much has Microsoft invested in OpenAI?
Microsoft's cumulative OpenAI investment is publicly reported in the $13B+ range across multiple rounds since 2019. The investment includes a mix of cash, Azure cloud credits, and other consideration. The exact 2026 totals reflect additional rounds we've covered through the period.
Does Microsoft own OpenAI?
No. Microsoft holds a substantial economic interest in OpenAI's for-profit subsidiary (entitled to a capped return on its investment) but does not own OpenAI outright. Governance decisions sit with the OpenAI nonprofit board, not Microsoft.
Is the Microsoft–OpenAI relationship still strong in 2026?
Yes, but with more public friction than the early years. Both companies have hedged: Microsoft has invested in alternative model providers and built its own foundation models; OpenAI has expanded compute deals beyond Azure. The partnership remains the dominant relationship for both.
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