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Microsoft (MSFT) — Deep Dive

Prices as of the Mon 05 Oct 2026 close · data pulled 2026-10-06 07:28:00+00:00 · refreshed weekly · methodology

Not investment advice

Educational analysis built from public data (Yahoo Finance, Kenneth French Data Library) and explicit model assumptions. Numbers update automatically; the qualitative notes are dated.

Verdict: Hold — 4/8 checks pass

Microsoft is profitable on an owner-FCF basis, with net debt of USD 52.0bn and consensus revenue of 391.2bn for FY2027 and 468.0bn for FY2028 (+20%). At USD 525.18 the market prices in 25% a year revenue growth after FY2028 (fading to 4%) at a 26% owner-FCF margin, or a 38% margin on the base growth path. The base-case DCF is USD 356 (-32%).

Check Pass Evidence
Valuation: base-case DCF at or above price ❌ base DCF USD 356 vs price USD 525
Relative value: forward P/E at most 1.2x the peer median ✅ 22.2x FY2028E vs peer median 23.0x
Street: de-biased, shrunk analyst alpha > 0 (ch27) ❌ -2.3%
Momentum: 12-1 month return > 0 (ch11) ❌ -0%
Trend: price above 200-day MA (ch12) ✅ +22% vs 200DMA
Not overbought: RSI(14) below 70 ✅ RSI 66
Fundamentals: revenue growing and FCF positive ✅ revenue +18% y/y, TTM FCF 67.0bn
Balance sheet: net cash ❌ net cash -52.0bn

Snapshot

Metric Value Metric Value
Price USD 525.18 Market cap USD 3,899.7bn
Enterprise value USD 3,951.7bn Net cash USD -52.0bn
52-week range 352.17 – 537.65 From 52w high -2.3%
Trailing P/E (GAAP) 29.3x Forward P/E FY2027 / FY2028 26.6x / 22.2x
PEG (FY+1 P/E ÷ EPS growth) 1.12 EV / TTM revenue 11.9x
TTM revenue USD 331.8bn TTM FCF / after SBC 67.0bn / 54.6bn
Beta vs SPY (raw / Blume) 1.10 / 1.07 Realized vol 20d / 1y 21% / 32%
Analysts / mean target 53 / USD 583 (+10.9%) Next earnings 2026-10-28
Shares out (diluted proxy) 7.426bn Short interest (% float) 0.9%
Sector ETF benchmark XLK Cash runway (cash ÷ FCF burn) n/a (FCF positive)
Institutions / insiders 76% / 0.09% Dividend USD 3.92

1. Price over time

Price history

Ticker 1M 3M 6M YTD 1Y 3Y 5Y 10Y 10Y CAGR
MSFT +5% +36% +41% +9% +2% +64% +90% +926% 26.2%
XLK +7% +10% +47% +40% +42% +143% +178% +834% 25.0%
SPY +1% +3% +18% +15% +17% +87% +91% +321% 15.5%
AAPL +4% +7% +29% +23% +29% +90% +142% +1188% 29.1%
GOOGL +2% -5% +16% +11% +42% +154% +157% +773% 24.2%
AMZN -3% +3% +18% +9% +15% +96% +56% +495% 19.5%
ORCL -10% -1% -1% -26% -50% +34% +67% +323% 15.5%
CRM -11% +39% +25% -13% -4% +13% -14% +242% 13.1%

Largest one-day moves in the last 5 years: 30 Jul 2026 +15.5%, 29 Jan 2026 -10.0%, 09 Apr 2025 +10.1%, 26 Oct 2022 -7.7%, 10 Nov 2022 +8.2%.

2. Return and risk (ch.5)

Statistics use the 60 complete months to Sep 2026.

Statistic Value What it means
Arithmetic mean (annualized) 16.4% Expected one-period return if the past repeats
Geometric mean (CAGR) 13.6% What a buy-and-hold investor actually earned; the gap ≈ σ²/2 is volatility drag
Standard deviation (annualized) 27.3% 1.7× the S&P 500's 15.7%
Skewness / excess kurtosis 0.42 / 0.42 Right-skewed, fat tails vs normal
5% monthly VaR: historical / normal -10.0% / -11.6% One month in 20 loses at least this much
5% monthly expected shortfall -13.0% Average loss in that worst 5% of months
Sharpe ratio (S&P 500) 0.47 (0.67) Excess return per unit of total risk
Sortino ratio 0.80 Excess return per unit of downside risk
Max drawdown, 5y -37.1% (trough Nov 2022) Currently -2.3% from the peak

Risk

3. Index model, CAPM and factors (ch.8–10)

Regression (60m excess returns) Alpha (ann.) t(α) Beta t(β) R² Residual σ
vs SPY +1.3% 0.13 1.10 6.18 0.40 21.2%
vs XLK -1.3% -0.14 0.73 6.37 0.41 20.9%
  • Risk decomposition (ch.8): systematic variance β²σ²(M) = 3.0% vs firm-specific σ²(e) = 4.5%, so 40% of the risk is market-driven and 60% is diversifiable.
  • CAPM required return (ch.9): k = r_f + β × MRP = 4.02% + 1.10 × 5.5% = 10.1% (Blume-adjusted β 1.07 → 9.9%, used as the DCF discount rate).
  • Historical alpha of +1.3% a year has a t-stat of 0.13: not statistically distinguishable from zero (ch.11: past alpha is a weak guide).
  • Fama-French 5 factors + momentum (ch.10, 150 months to Jul 2026): R² 0.58, alpha +8.2% (t 1.78). Loadings: Mkt-RF +1.01 (t 10.9), SMB -0.74 (t -4.7), HML -0.39 (t -2.6), RMW +0.30 (t 1.7), CMA -0.11 (t -0.5), Mom -0.25 (t -2.3). The loadings describe a large-cap, growth, high-profitability return profile (SMB > 0 small-cap, HML < 0 growth, RMW < 0 weak profitability, CMA < 0 aggressive investment).

Rolling beta

4. Portfolio fit: allocation and diversification (ch.6–7)

Correlation of monthly returns with MSFT (60m): XLK 0.64, SPY 0.63, AAPL 0.51, GOOGL 0.43, AMZN 0.62, ORCL 0.61, CRM 0.60.

  • A 50/50 mix with SPY would have had volatility of 19.6% vs 21.5% for the weighted average of the two, a diversification benefit because ρ = 0.63 < 1.
  • Optimal risky share y* = [E(r) − r_f] / (A·σ²), holding MSFT alone against T-bills (σ = 27.3%):
Risk aversion A y* with CAPM E(r) y* with E(r) + Street α
2 41% 25%
3 27% 17%
4 20% 13%
6 14% 8%

Even a risk-tolerant investor would put only a modest share in a single stock this volatile. Ch.7–8 say the efficient choice is the market portfolio plus a Treynor-Black tilt (section 9), not a concentrated position.

5. Financial statements: quality of earnings (ch.19)

Quarter Revenue Q/Q Gross m. Op. m. (GAAP) Net m. R&D % SBC % Diluted EPS FCF FCF m. DSO (days) DIO (days)
2025-06 76.4bn n/a 68.6% 44.9% 35.6% 11.6% 4.0% 3.65 25.57bn 33.4% 83 4
2025-09 77.7bn +2% 69.0% 48.9% 35.7% 10.5% 3.8% 3.72 25.66bn 33.0% 62 4
2025-12 81.3bn +5% 68.0% 47.1% 47.3% 10.5% 4.0% 5.16 5.88bn 7.2% 63 4
2026-03 82.9bn +2% 67.6% 46.3% 38.3% 10.8% 3.7% 4.27 15.80bn 19.1% 66 4
2026-06 90.0bn +9% 67.2% 45.1% 39.7% 11.1% 3.5% 4.81 19.64bn 21.8% 82 4

Fundamentals

  • DuPont, TTM: ROE 34.2% = net margin 40.3% × asset turnover 0.49 × leverage 1.73. Relative to typical levels (10% margin, 0.8 turnover, 2.0 leverage) the biggest driver is net margin.
  • Cash conversion: TTM operating cash flow 182.9bn vs net income 133.7bn. The accruals ratio of -7.3% of assets is negative (cash earnings exceed accounting earnings), a sign of high-quality earnings.
  • Stock-based compensation of 12.4bn TTM (3.7% of revenue) is a real cost to shareholders. The valuation below uses FCF after SBC (owner FCF margin 16.4%). Buybacks were 22.3bn; share count changed -0.1% over the year.
  • Operating leverage (ch.17): degree of operating leverage 1.17 (last two fiscal years): each 1% change in sales moved EBIT by about 1.2%.

6. Valuation (ch.18)

Valuation

Multiples vs peers (Yahoo Finance, TTM and next-year; peers chosen by hand in config.json):

Ticker Fwd P/E P/S TTM EV/EBITDA FCF yield Rev. growth FY Gross m. EBIT m. ROE TTM Target upside
MSFT 22.2x 11.8x 20.3x 0% 18% 68% 45% 34% 11%
AAPL 34.7x 10.4x 29.1x 2% 16% 49% 33% 149% -1%
GOOGL 23.0x 9.5x 23.9x 1% 24% 61% 34% 49% 24%
AMZN 24.0x 3.5x 16.8x 0% 20% 51% 14% 31% 32%
ORCL 13.0x 6.0x 16.5x -11% 30% 64% 36% 41% 67%
CRM 14.3x 4.3x 17.1x 9% 11% 77% 21% 19% 23%
Peer median 23.0x 6.0x 17.1x 1% 20% 61% 33% 41% 24%

Growth embedded in the price (PVGO). With FY2028E EPS of USD 23.68 and k = 9.9%, the no-growth value E₁/k is USD 239.39. PVGO = USD 285.79, which is 54% of the price, so most of the value depends on growth beyond FY2028. No-growth P/E = 1/k = 10.1x vs the actual 22.2x.

Constant-growth check. On TTM owner FCF, P = FCF₁/(k − g) implies a perpetual growth rate of 8.5%, above the 4% long-run nominal-GDP ceiling the book recommends for g.

Scenario DCF (owner FCF, k = 9.9%, terminal g = 4%). The revenue path is FY2027 (391.2bn), then the FY2028 low/avg/high estimate, then growth that fades linearly to 4% over 8 years. Owner-FCF margin ramps from today's 16.4% to the scenario margin over 3 years. Scenario assumptions are generic growth with hand-set steady-state margins (today's FCF is depressed by the AI data-centre capex build-out; margins are set near the pre-2024 owner-FCF level).

Scenario FY2028 revenue Growth after Owner-FCF margin FY2036 revenue Terminal value share Value / share vs price
Bear 433.2bn 7% 20% 671bn 63% USD 196 -63%
Base 468.0bn 14% 26% 966bn 66% USD 356 -32%
Bull 503.0bn 20% 32% 1,344bn 68% USD 595 +13%

Reverse DCF: what today's price assumes. On the base revenue path the price requires a steady-state owner-FCF margin of 38%. At the base 26% margin it requires 25% growth after FY2028, or a discount rate of 8.2% (vs the model's 9.9%).

Sensitivity: base revenue path, value per share by discount rate (rows) and steady-state owner-FCF margin (columns).

k \ margin 16% 21% 26% 31% 36%
6.9% 478 627 776 925 1,073
7.9% 348 456 564 671 779
8.9% 271 354 438 522 606
9.9% 220 288 356 424 492
10.9% 184 241 298 355 412

Earnings-multiple cross-check: FY2028E EPS USD 23.68 × 20x = 474, 25x = 592, 30x = 710, 35x = 829, 40x = 947, 45x = 1,065. The price implies 22x. The FY2028 EPS range across analysts is 22.08–26.00.

7. Market efficiency and earnings reactions (ch.11)

Market-model abnormal returns (vs SPY, estimated over the 250 days before each event) for the last 12 releases:

Announced Reaction day EPS vs est. Surprise AR day 0 CAR [−1,+1] Drift CAR [+2,+20]
2026-07-29 2026-07-30 4.74 vs 4.24 11.8% +14.4% +17.6% +9.1%
2026-04-29 2026-04-30 4.27 vs 4.07 4.9% -4.8% -4.4% +5.4%
2026-01-28 2026-01-29 4.14 vs 3.92 5.7% -9.8% -10.1% -7.6%
2025-10-29 2025-10-30 4.13 vs 3.66 12.7% -1.9% -4.0% -5.7%
2025-07-30 2025-07-31 3.65 vs 3.38 8.1% +4.3% +4.3% -6.8%
2025-04-30 2025-05-01 3.46 vs 3.22 7.4% +7.0% +8.3% +3.0%
2025-01-29 2025-01-30 3.23 vs 3.12 3.5% -6.7% -6.5% -1.4%
2024-10-30 2024-10-31 3.30 vs 3.11 6.1% -3.9% -2.8% -1.7%
2024-07-30 2024-07-31 2.95 vs 2.94 0.2% -3.0% -1.9% -4.5%
2024-04-25 2024-04-26 2.94 vs 2.84 3.4% +0.7% -2.9% +1.6%
2024-01-30 2024-01-31 2.93 vs 2.77 5.8% -0.9% -1.3% -4.0%
2023-10-24 2023-10-25 2.99 vs 2.65 12.8% +5.0% +2.1% +0.1%
  • Average absolute day-0 abnormal move: 5.2%. The sign of the EPS surprise matched the sign of the reaction 42% of the time, which is close to a coin flip: guidance and commentary matter more than the headline EPS beat.
  • Post-announcement drift: the correlation between the initial reaction and the next-20-day drift is 0.61. A positive value hints at under-reaction (PEAD, ch.11–12), though with only 12 events the evidence is weak.

Event study

8. Technicals and behavioural signals (ch.12)

Indicator Value Read
Price vs 50-day / 200-day MA +7% / +22% Golden cross (50 > 200)
RSI(14) 66 Neutral
12-1 month momentum -0% Negative (Jegadeesh-Titman)
6-month relative strength vs XLK -4% Laggard
Insider sales / purchases, last 6m USD 0.08bn / USD 0.00bn Net selling, often planned 10b5-1 sales; insider buying is the informative signal (ch.11)
Analyst actions, last 90 days 36 actions, 19 target raises Targets chasing the price is a sign of anchoring and herding (ch.12)
Recent targets below current price 25% Most targets still sit above the price
Ratings (strong buy / buy / hold / sell) 14 / 41 / 1 / 0 Near-unanimous bullishness is crowded positioning
FY2028 EPS estimate: now vs 90 days ago 23.68 vs 22.60 +5% revision; up/down revisions in the last 30 days: 1/1

9. Treynor-Black: should an active manager overweight it? (ch.27)

Step Value
Analyst-implied 12m return (mean target / price − 1) +10.9%
CAPM 1-year required return (raw β) 10.1%
Raw alpha +0.9%
Minus average analyst optimism bias (Top-30 cross-section) -9.9%
Shrunk alpha (× 0.25, for forecast imprecision) -2.3%
Residual variance σ²(e) 4.5%
Initial active weight w₀ = [α/σ²(e)] / [E(R_M)/σ²_M] -22.5%
Beta-adjusted weight w* = w₀ / [1 + (1 − β)w₀] -22.0%

A negative weight means an active manager would underweight it relative to the index.

10. Options market view (ch.20–21)

IV term structure

Expiry Days ATM IV Implied ±1σ move to expiry 90% put − 110% call IV (skew)
2026-10-12 7 24% ±3.3% (±17) +13.0%
2026-10-14 9 26% ±4.0% (±21) +10.1%
2026-10-16 11 25% ±4.4% (±23) +4.4%
2026-10-23 18 24% ±5.4% (±28) +4.9%
2026-10-30 25 34% ±8.9% (±47) +2.4%
2026-11-06 32 33% ±9.9% (±52) +0.3%
2026-11-13 39 32% ±10.6% (±55) +4.3%
2026-11-20 46 31% ±10.9% (±57) +3.4%
2026-12-18 74 29% ±13.2% (±69) +3.8%
2027-01-15 102 28% ±15.0% (±79) +1.4%
2027-03-19 165 30% ±20.0% (±105) +1.3%
2027-04-16 193 31% ±22.8% (±120) +0.4%
2027-06-17 255 32% ±26.5% (±139) +1.6%
2027-09-17 347 32% ±31.2% (±164) +0.2%
  • Earnings-implied move: the jump in variance from the 2026-10-23 expiry (IV 24%) to 2026-10-30 (IV 34%) prices an earnings-day move of ±6.3% (1σ), or about ±5.0% in absolute terms (≈ ±26). Compare the historical average absolute reaction of 5.2% in section 7.
  • Implied vs realized: the ~1-month ATM IV is 33% vs realized 21% (20d) / 38% (60d) / 32% (1y). Options are cheap relative to recent realized volatility, so buying protection is relatively inexpensive.
  • Put-call parity (ch.20): at the ATM strike for 2026-11-06, C − P − (S − PV(K)) = -0.03 per share. Close to zero, as parity requires.
  • Quotes were unavailable when the data was pulled (outside market hours), so implied vols use each contract's last trade price. Treat them as approximate; illiquid strikes can be stale.

Premium-selling menu for holders: the last expiry before earnings (2026-10-23), about 0.15/0.20/0.25/0.30 delta.

Type Strike Bid / Ask Price IV Delta P(expires OTM) Distance Yield Annualized OI
Call 545 – 4.35 24% +0.26 75% +3.8% 0.83% 17% –
Call 550 – 3.38 24% +0.21 80% +4.7% 0.64% 13% –
Call 560 – 1.87 25% +0.13 88% +6.6% 0.36% 7% –
Put 495 – 2.38 27% -0.14 84% -5.7% 0.48% 10% –
Put 500 – 3.15 26% -0.18 80% -4.8% 0.63% 13% –
Put 505 – 3.73 25% -0.22 76% -3.8% 0.74% 15% –
Put 510 – 5.50 26% -0.28 70% -2.9% 1.08% 22% –

Calls = covered calls on shares you own (yield on the share price); puts = cash-secured puts (yield on the strike). Prices are last trades at the data pull and indicative only; check live quotes before trading.

11. Our hourly signal model

MSFT is not in the Top-30 signal universe.

12. Qualitative analysis: business, PEST, catalysts and risks

Qualitative notes reviewed 2026-10-06

These notes are written by hand, unlike the auto-refreshed numbers above. Events up to late 2025 come from company announcements. Later developments are inferred from the data (consensus estimates, price reactions) and should be checked against MSFT's 10-Q/10-K filings and earnings calls.

Business in one paragraph

Microsoft is the operating-system, productivity-software and cloud-infrastructure incumbent, with revenue from Productivity and Business Processes, Intelligent Cloud, and More Personal Computing. Office, Windows and LinkedIn provide durable cash generation, while Azure, server products, GitHub, security and AI services drive growth. Gaming became larger after Activision Blizzard, but the stock is still valued mainly on whether Azure and Copilot can turn AI infrastructure spending into high-margin recurring revenue. The case hinges on Microsoft preserving enterprise trust, monetizing AI across the installed base, and avoiding a capex cycle where demand consumes cash faster than software margins expand.

Key developments

When Event Why it matters
Oct 2023 Closed the Activision Blizzard acquisition Added large gaming content, mobile exposure and subscription optionality, while also increasing regulatory scrutiny.
Nov 2023 Microsoft 365 Copilot became generally available for enterprises Started the test of whether generative AI can lift per-seat revenue in Office, Teams, security and developer workflows.
Sep 2024 Announced a new USD 60bn buyback authorization and a higher dividend Signaled that AI capex would coexist with shareholder returns rather than replace them entirely.
Jan 2025 Microsoft described roughly USD 80bn of FY2025 AI data-center investment, more than half in the US (reported) Made AI infrastructure the central capital-allocation question for Azure and Copilot economics.
Oct 2025 Microsoft and OpenAI reset partnership terms around OpenAI's new structure and long-term Azure commitments (reported) Reduced governance uncertainty, but kept Microsoft exposed to OpenAI dependency and AI capacity needs.

PEST analysis

Factor Tailwinds Headwinds Net
Political US and allied governments want trusted domestic cloud, security and AI suppliers. Defense, public-sector and sovereign-cloud demand support Azure. Antitrust scrutiny covers bundling, cloud licensing and AI partnerships. Export controls and data-residency rules complicate global AI capacity. ⚖️
Economic Mission-critical enterprise subscriptions, large cash flow, and cloud migration provide resilience. AI can raise average revenue per user. AI data centers pull forward depreciation, power costs and GPU commitments. Slower IT budgets would delay Copilot seat expansion. ⚖️
Social Copilot sits inside daily workflows, making adoption easier than standalone AI tools. GitHub has strong developer mindshare. Enterprises remain cautious about data leakage, hallucinations, labor impact and AI governance. Windows consumer relevance is less dominant than in past cycles. ✅
Technological Azure AI, GitHub Copilot, security telemetry and OpenAI models create a broad platform. Custom silicon can reduce dependence on merchant GPUs over time. NVIDIA supply, power availability and OpenAI concentration are constraints. Google, Amazon and open-source models pressure differentiation. ✅

Bull case vs bear case

  • Bull: Azure keeps taking cloud share, Copilot attachment improves steadily, and AI infrastructure becomes a high-utilization software platform rather than stranded capacity. Office, GitHub, security and LinkedIn make Microsoft one of the few companies able to distribute AI directly into paid enterprise workflows.
  • Bear: AI spending outruns monetization, OpenAI bargaining power rises, and regulators force changes to bundling or cloud licensing. If customers treat Copilot as a nice-to-have add-on in a slower economy, margins could compress even while reported revenue keeps growing.

Catalysts to watch (next 6–12 months)

  1. Late October 2026 or early November 2026 Q1 FY2027 results, especially Azure growth and AI capacity commentary.
  2. Copilot adoption metrics, renewal behavior and evidence of productivity-suite price realization.
  3. OpenAI governance, model-access and Azure commitment updates.
  4. AI capex, power availability and depreciation guidance for FY2027.
  5. Regulatory developments in US, EU and UK cloud and AI investigations.

What would change the verdict

  • More constructive: Azure growth reaccelerating with stable margins, Copilot usage moving from pilots to broad renewals, and capex guidance showing better utilization of AI clusters.
  • More cautious: estimate revisions turning negative, OpenAI economics becoming less favorable, or regulatory remedies that weaken Microsoft bundling advantages.

Generated by analyses/deep-dives/deep_dive.py. Quantitative sections refresh weekly; the qualitative notes carry their own review date.