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Copilot Cowork puts Anthropic's brain in the enterprise operating system

MSFT has closed the print week up in 0 of its last 3 prints; the median move is 0.5%.Tech Startup·Website
Ticker
MSFT
Beat
ai
Size
Enterprise (5,000+)
Revenue
$90.0B
as of Jun 2026
Cash
$20.9B
as of Jun 2026
Researched · Fresh
1 day ago

Microsoft embedded Anthropic's Claude into M365 Copilot as 'Copilot Cowork' — $30/seat/month for autonomous AI agents that run across your emails, files, and meetings. The $99/seat E7 bundle is Microsoft's play to own the enterprise AI operating system.

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MSFT · weekly close
521.91 USD−0.5%
Friday 30 Oct 2026 · last 52 Fridays 356.77–535.07
pick a pin
Every pin is a dated row
Solid: filed with the SEC, settled at FINRA, or a recorded split. Hollow: the scheduled print, past the last close, never a price.
  1. Insiders sold, 90 days: 63,170 sh · 6 filings, Form 4 · 15 Oct 2026
  2. Short interest: 65,674,557 sh · 3.18 days to cover, FINRA · settled 15 Oct 2026
  3. Insiders bought, 90 days: 105,306 sh · 5 filings, Form 4 · 15 Sept 2026
  4. Next print: in 84 days, Scheduled · 26 Jan 2027, scheduled
521.91USD-0.5%ai -2.6%MSFT · 112 weekly closes to 2026-10-30

Who is buying

Insiders sold, last 90 daysSEC Form 4 · newest 15 Oct 2026
6 filings · 63,170 shares
Insiders bought, last 90 daysSEC Form 4 · newest 15 Sept 2026
5 filings · 105,306 shares
Shares sold shortFINRA · settled 15 Oct 2026
65,674,557 shares
Days to unwind the shortFINRA · settled 15 Oct 2026
3.18
see the whole series
Financials

The reported figures

Revenue · quarterly
$90.0B
latest, Q2 ’26 · 12 periods stored
Filed · primary
Q2 ’26
$90.0B USD
as of 30 Jun 2026
Source: sec.gov
Microsoft, quarterly figures held, Q3 ’23 to Q2 ’26
PeriodAs ofRevenueGross marginOperating marginFree cash flowCapexCashShares outstandingGradingSource
Q3 ’2330 Sept 2023$56.5B USD—47.6% share of revenue$20.7B USD$9.9B USD$80.5B USD7.43B sharesFiled · primarysec.gov
Q4 ’2331 Dec 2023$62.0B USD—43.6% share of revenue$9.1B USD$9.7B USD$17.3B USD7.43B sharesFiled · primarysec.gov
Q1 ’2431 Mar 2024$61.9B USD—44.6% share of revenue$21.0B USD$11.0B USD$19.6B USD7.43B sharesFiled · primarysec.gov
Q2 ’2430 Jun 2024$245B USD———$44.5B USD——Filed · primary10-K FY2024 filed 2024-07-30 (XBRL)
Q3 ’2430 Sept 2024$65.6B USD—46.6% share of revenue$19.3B USD$14.9B USD$20.8B USD7.43B sharesFiled · primarysec.gov
Q4 ’2431 Dec 2024$69.6B USD—45.5% share of revenue$6.5B USD$15.8B USD$17.5B USD7.43B sharesFiled · primarysec.gov
Q1 ’2531 Mar 2025$70.1B USD—45.7% share of revenue$20.3B USD$16.7B USD$28.8B USD7.43B sharesFiled · primarysec.gov
Q2 ’2530 Jun 2025$282B USD68.8% share of revenue45.6% share of revenue—$64.6B USD$94.6B USD7.43B sharesFiled · primary10-K FY2025 filed 2025-07-30 (XBRL + filing)
Q3 ’2530 Sept 2025$77.7B USD69.0% share of revenue48.9% share of revenue$25.7B USD$19.4B USD——Filed · primary10-Q filed 2025-10-29 (XBRL)
Q4 ’2531 Dec 2025$81.3B USD68.0% share of revenue47.1% share of revenue$5.9B USD$29.9B USD——Filed · primary10-Q filed 2026-01-28 (XBRL)
Q1 ’2631 Mar 2026$82.9B USD67.6% share of revenue46.3% share of revenue$15.8B USD$30.9B USD$78.3B USD7.43B sharesFiled · primary10-Q filed 2026-04-29 (XBRL + filing)
Q2 ’2630 Jun 2026$90.0B USD—45.1% share of revenue$19.6B USD$35.8B USD$20.9B USD7.43B sharesFiled · primarysec.gov

Microsoft’s figures as the company reported them in its filings. Quarters are calendar quarters, so a company whose year ends in January shows each fiscal quarter under the calendar quarter it falls in. An empty slot is a quarter we hold no figure for.

Revenue · quarterlyQ3 ’23 – Q2 ’26
$90.0B-68% vs Q2 ’25

Q2 ’26 · as of Jun 2026

Revenue Q3 ’23: $56.5B, as of Sep 2023Revenue Q4 ’23: $62.0B, as of Dec 2023Revenue Q1 ’24: $61.9B, as of Mar 2024Revenue Q2 ’24: $245B, as of Jun 2024Revenue Q3 ’24: $65.6B, as of Sep 2024Revenue Q4 ’24: $69.6B, as of Dec 2024Revenue Q1 ’25: $70.1B, as of Mar 2025Revenue Q2 ’25: $282B, as of Jun 2025Revenue Q3 ’25: $77.7B, as of Sep 2025Revenue Q4 ’25: $81.3B, as of Dec 2025Revenue Q1 ’26: $82.9B, as of Mar 2026Revenue Q2 ’26: $90.0B, as of Jun 2026
Operating margin · quarterlyQ3 ’23 – Q2 ’26
45.1%-0.5 pts vs Q2 ’25

Q2 ’26 · as of Jun 2026

Operating margin Q3 ’23: 47.6%, as of Sep 2023Operating margin Q4 ’23: 43.6%, as of Dec 2023Operating margin Q1 ’24: 44.6%, as of Mar 2024Operating margin Q3 ’24: 46.6%, as of Sep 2024Operating margin Q4 ’24: 45.5%, as of Dec 2024Operating margin Q1 ’25: 45.7%, as of Mar 2025Operating margin Q2 ’25: 45.6%, as of Jun 2025Operating margin Q3 ’25: 48.9%, as of Sep 2025Operating margin Q4 ’25: 47.1%, as of Dec 2025Operating margin Q1 ’26: 46.3%, as of Mar 2026Operating margin Q2 ’26: 45.1%, as of Jun 2026
Free cash flow · quarterlyQ3 ’23 – Q2 ’26
$19.6B

Q2 ’26 · as of Jun 2026

Free cash flow Q3 ’23: $20.7B, as of Sep 2023Free cash flow Q4 ’23: $9.1B, as of Dec 2023Free cash flow Q1 ’24: $21.0B, as of Mar 2024Free cash flow Q3 ’24: $19.3B, as of Sep 2024Free cash flow Q4 ’24: $6.5B, as of Dec 2024Free cash flow Q1 ’25: $20.3B, as of Mar 2025Free cash flow Q3 ’25: $25.7B, as of Sep 2025Free cash flow Q4 ’25: $5.9B, as of Dec 2025Free cash flow Q1 ’26: $15.8B, as of Mar 2026Free cash flow Q2 ’26: $19.6B, as of Jun 2026

Operating cash flow minus capital spending.

Cash · quarterlyQ3 ’23 – Q2 ’26
$20.9Bdebt $40.3B

Q2 ’26 · as of Jun 2026

Cash Q3 ’23: $80.5B, as of Sep 2023Cash Q4 ’23: $17.3B, as of Dec 2023Cash Q1 ’24: $19.6B, as of Mar 2024Cash Q3 ’24: $20.8B, as of Sep 2024Cash Q4 ’24: $17.5B, as of Dec 2024Cash Q1 ’25: $28.8B, as of Mar 2025Cash Q2 ’25: $94.6B, as of Jun 2025Cash Q1 ’26: $78.3B, as of Mar 2026Cash Q2 ’26: $20.9B, as of Jun 2026Debt Q3 ’23: $45.7B, as of Sep 2023Debt Q4 ’23: $47.2B, as of Dec 2023Debt Q1 ’24: $44.9B, as of Mar 2024Debt Q3 ’24: $45.1B, as of Sep 2024Debt Q4 ’24: $45.0B, as of Dec 2024Debt Q1 ’25: $42.9B, as of Mar 2025Debt Q2 ’26: $40.3B, as of Jun 2026

CashDebt

Shares outstanding · quarterlyQ3 ’23 – Q2 ’26
7.43B-0.1% since Q3 ’23

Q2 ’26 · as of Jun 2026

Shares outstanding Q3 ’23: 7.43B, as of Sep 2023Shares outstanding Q4 ’23: 7.43B, as of Dec 2023Shares outstanding Q1 ’24: 7.43B, as of Mar 2024Shares outstanding Q3 ’24: 7.43B, as of Sep 2024Shares outstanding Q4 ’24: 7.43B, as of Dec 2024Shares outstanding Q1 ’25: 7.43B, as of Mar 2025Shares outstanding Q2 ’25: 7.43B, as of Jun 2025Shares outstanding Q1 ’26: 7.43B, as of Mar 2026Shares outstanding Q2 ’26: 7.43B, as of Jun 2026

A rising count is dilution: each existing share owns less of the company.

Latest filing: sec.gov

The record

What happened

What happened
DateTypeWhat happenedSource
2026-11-02funding round424B2: $25bn senior notes in ten series (2028-2066)Prospectus supplement for $25,000,000,000 across ten series (2028 and 2029 floating and fixed, 2031, 2033, 2036, 2046, 2056, 2066); fixed coupons 4.850%-6.350%; original issue date 4 Nov 2026; proceeds for general corporate purposes.agent:company-events · SEC EDGAR 424B2
2026-11-02editorial noteCapex figure revised: $190B → $39,367MCapex moved from $190B (deep-dive-2026-08-06.md) to $39,367M (deep-dive-2026-11-02.md).dossier
2026-11-02editorial noteMargin figure revised: 67% → $62,559MMargin moved from 67% (deep-dive-2026-08-06.md) to $62,559M (deep-dive-2026-11-02.md).dossier
2026-11-02editorial noteRevenue figure revised: $90.0B → $92,279MRevenue moved from $90.0B (deep-dive-2026-08-06.md) to $92,279M (deep-dive-2026-11-02.md).dossier
2026-10-28filing8-K: Microsoft recasts FY2024-2026 segment figuresRecasts three years to 30 Jun 2026 for new segments (Agents and Infra; Devices and Consumer) per Ex. 99.1; states it is not a restatement.agent:company-events · SEC EDGAR 8-K
2026-10-28filing10-Q: Microsoft Q1 FY2027 revenue $92,279mQuarter ended 30 Sep 2026: revenue $92,279M (prior year: $77,673M); net income $36,629M; diluted EPS $4.92.agent:company-events · SEC EDGAR 10-Q
2026-10-28guidance8-K: Microsoft Q1 FY2027 revenue $92.3bnQ1 FY2027 revenue $92,279m (+19%); operating income $45,915m; GAAP net income $36,629m, $4.92 diluted EPS; Microsoft Cloud revenue $63.9bn (+30%).agent:company-events · SEC EDGAR 8-K
2026-08-06editorial noteVerdict changed: NOT ISSUED — this refresh is scoped to definitional resolution (capex, backlog) ahead of the 2026-07-29 print. No directional call taken; Lenses 12/13 deferred under the Socratic gat…Before (deep-dive-2026-07-22.md): NOT ISSUED — this refresh is scoped to definitional resolution (capex, backlog) ahead of the 2026-07-29 print. No directional call taken; Lenses 12/13 deferred under the Socratic gate. After (deep-dive-2026-08-06.md): NOT ISSUED — the 2026-07-22 refresh withheld a directional call under the Socratic gate and this one keeps that discipline. What it does deliver: the print answered all eight of the prior dossier's ranked questions, and two of them came back opposite to the worry.dossier
2026-07-22editorial noteVerdict changed: The cleanest AI-infrastructure compounder on the board, now de-rated to ~20x forward on a real fear — Azure deceleration meeting a $190B/yr capex wall — that is more a timing questio…Before (deep-dive-2026-06-18.md): The cleanest AI-infrastructure compounder on the board, now de-rated to ~20x forward on a real fear — Azure deceleration meeting a $190B/yr capex wall — that is more a timing question than a thesis-breaker; the moat (RPO $633B, M365 distribution, ~27% of OpenAI) is intact, the FCF is the variable to watch. After (deep-dive-2026-07-22.md): NOT ISSUED — this refresh is scoped to definitional resolution (capex, backlog) ahead of the 2026-07-29 print. No directional call taken; Lenses 12/13 deferred under the Socratic gate.dossier
Compute market

Deals on the Ledger

The compute board →
Published compute deals with Microsoft as a party
AnnouncedWithTypeValueSource
19 Aug 2026
  • ChronoScale Provider
Capacity contractundisclosedChronoScale 8-K, filed 2026-08-27
18 Nov 2025Capacity contract$30B$30B Azure purchase commitment; the up-to-1 GW of additional contracted capacity is on top of it.Anthropic announcement, 2025-11-18
3 Nov 2025Capacity contract$9.7BIREN 8-K, 2025-11-03
28 Oct 2025Capacity contract$250B$250B incremental Azure purchase commitment; no term stated.Microsoft blog, 2025-10-28
15 Oct 2025Capacity contractundisclosedNo dollar value disclosed; multi-year.Nscale press release, 2025-10-15
8 Sept 2025Capacity contract$17.4B~$17.4B total contract value through 2031; up to ~$19.4B if Microsoft acquires additional services/capacity.Nebius 6-K, 2025-09-08

Every Microsoft deal on the Ledger — each one read against its source.

dossier age
1 days
researched 2 Nov 2026 · ring fills at 180
pick a section
Each column is a section of the dossier
Its height is how many times the section names a filing: 16 mentions across 2 sections. A dashed foot names none.
Primary sources
  1. The dossier: Refresh delta (since 2026-08-06), 429 words, 16 filing mentions
  2. The dossier: What held, 47 words, no filing mention
Research

The Microsoft dossier

The verdict

NOT ISSUED — the 2026-07-22 refresh withheld a directional call under the Socratic gate and this one keeps that discipline. What it does deliver: the print answered all eight of the prior dossier's ranked questions, and two of them came back opposite to the worry.

Refresh delta (since 2026-08-06)

  1. New segments from FY27. Microsoft moved from three segments to two: Agents and Infra (Microsoft Cloud, productivity and server licensing, consulting and support) and Devices and Consumer (Windows, XBOX, advertising). Azure was redefined: GitHub cloud and Security Copilot moved to Microsoft 365 commercial cloud, and Healthcare and Life Sciences cloud moved to a new Industry solutions metric [Form 8-KA filing for something that happened between reports and matters enough to tell shareholders now. segments]. FY2026 Form 10-KA company’s audited annual report to the US regulator. The most complete thing it publishes. figures were recast to the new structure [8-K recast]. The prior dossier's Azure, Intelligent Cloud and segment figures are on the old basis and do not compare directly with what follows.

  2. FY27 Q1 actuals: revenue $92,279M, +19% (prior-year quarter: $77,673M); gross margin $62,559M, 67.8%; operating income $45,915M, +21%, 49.8% of revenue; net income $36,629M, GAAP diluted EPS $4.92 (+32%); non-GAAP EPS, excluding OpenAI investment effects, $4.89 (+18%) [8-K Q1; Form 10-QThe quarterly version of the annual report. Lighter, and not audited. Q1].

  3. Segments and metrics: Agents and Infra $76,795M (+25%); Devices and Consumer $15,484M (−3%). Microsoft Cloud $63.9B (+30%); Azure +48% on the new definition; Microsoft 365 commercial cloud +17%; search and advertising ex-TAC +12%; Windows OEM and devices −22% [8-K Q1]. Microsoft Cloud gross margin fell to 66%, which the 10-Q puts down to the mix shift to Azure [10-Q Q1, MD&A].

  4. Commercial RPO: $677B, +73% YoY, weighted-average duration about 2.3 years; total-company RPO $683B [10-Q Q1, revenue note; 8-K Q1]. The prior dossier recorded $678B at 2026-06-30, so the commercial figure was about flat sequentially. About 30% is expected to be recognised in the next 12 months [10-Q Q1].

  5. OpenAI is now quantified as a customer. Revenue from commercial arrangements with OpenAI, including revenue-sharing payments, was $10.0B in the quarter; receivables from OpenAI were $7.2B (2026-06-30: $6.0B). Microsoft's equity-method stake is about 24% on an as-converted basis; OpenAI investment effects added $272M of net gains to other income [10-Q Q1, related-party note]. $10.0B is about 11% of quarterly revenue.

  6. Capex and cash: additions to property and equipment $39,367M (prior-year quarter $19,394M); finance-lease right-of-use assets obtained $5,192M; operating-lease assets obtained $6,523M [10-Q Q1, cash-flow statement and lease note]. Cash plus finance leases is $44,559M; management's own Capital expenditureMoney spent on long-lived things — buildings, machines, servers — rather than on running costs. figure is on the call, not read. Operating cash flow $58,000M, so cash flow less cash PP&E was $18,633M. The prior dossier's guide of "over $50 billion" for the quarter was on management's definition, so it is not tested here.

  7. Capital return and balance sheet: $10.2B returned in dividends and buybacks [8-K Q1]; $4,850M of debt repaid. Cash and short-term investments $64,509M (2026-06-30: $76,843M); debt $35,481M (2026-06-30: $40,294M) [10-Q Q1, balance sheet; estimate: current plus long-term portions]. Headcount fell 2% YoY [10-Q Q1, MD&A].

What held

  • Azure keeps accelerating on its own reported basis (+48%), and Microsoft Cloud growth rose to 30% (fact 3).
  • Free cash flowCash left after paying to run and maintain the business. Unlike profit, it is hard to flatter with accounting choices. stayed positive, as the FY27 guide promised (fact 6).
  • The operating margin held near 50% despite the cloud gross-margin dip (facts 2, 3).

How our view changed

4 dossiers

Every dossier we have written on Microsoft, newest first.

  1. current

    NOT ISSUED — the 2026-07-22 refresh withheld a directional call under the Socratic gate and this one keeps that discipline.

  2. NOT ISSUED — the 2026-07-22 refresh withheld a directional call under the Socratic gate and this one keeps that discipline.

  3. NOT ISSUED — this refresh is scoped to definitional resolution (capex, backlog) ahead of the 2026-07-29 print.

  4. The cleanest AI-infrastructure compounder on the board, now de-rated to ~20x forward on a real fear

Research trail

The research around Microsoft

Covered in the Knowledge Base

Models

Company details

IndustrySoftware
TypeTech Startup
SizeEnterprise (5,000+)
WebsiteVisit Microsoft

Others in ai

5 names

Where Microsoft sits against the other names we cover on this beat. Each line is that company’s verdict, not a summary of it.