Microsoft’s Silent Squeeze: Why 2026 Could Be the Year Investors Finally Jump Ship

Table of Contents

    Ben Rogers

    Ben Rogers is the Head of Growth at VaaSBlock, known for scaling real companies with real revenue in markets full of noise. He is a global growth operator who specialises in emerging technology, helping teams cut through hype, understand market behaviour, and execute with discipline.

     

    TL;DR

    Microsoft’s 2025 success story hides a quieter pattern: as AI capex surges and growth normalises, the company begins testing how much it can extract from captive ecosystems—developers, IT admins, and gamers—through pricing moves, deprecations, and “value alignment” emails. The warning sign isn’t one change; it’s the playbook: when the bill rises faster than the revenue story, tax the trapped.


     

    Microsoft’s Silent Squeeze

    Microsoft has entered the most dangerous phase of corporate success: universal admiration, rising costs, and a quiet shift from growth to extraction.

     

    2025, Microsoft a frog in boiling water, customer backlash 2025

     

    Disclosure: This is editorial analysis based on publicly available reporting, company filings, and product documentation. A consolidated list of references appears in Sources & Notes at the end.

    By mid‑2025, Microsoft had reached the most dangerous phase of corporate success: admiration without scrutiny. In public, the story is clean—record‑high confidence, a CEO treated like a steady‑handed custodian, and an AI halo powered by the OpenAI partnership and Copilot branding. But beneath the applause sits a darker, quieter tension: the AI bill is rising faster than the revenue proof, and the company is beginning to test how much it can extract from the people least able to leave—developers, IT admins, and gamers. That’s the “secret” hiding in plain sight. Not a scandal. A pattern. When growth normalises and capex spikes, the easiest lever is the captive user—through price hikes, deprecations, and “value alignment” emails that read like progress while functioning like toll booths.

    Satya Nadella walks into the Build keynote in May 2025, and the room feels like a cathedral roofed with light. He delivers the sentence that becomes wallpaper for the year—“We are the company shipping AI at scale”—and the applause rolls across Lake Washington. Live-bloggers type “unassailable” before the next slide. Fortune and Korn Ferry’s “Most Admired” list reinforces the mood: admiration without scrutiny. On CNBC, B‑roll loops of Nadella walking through chilled server halls built for machines, not people.

    Two days earlier, in the quieter theatre of an earnings call, Microsoft told a different story. CFO Amy Hood slipped a single sentence into her prepared remarks: “We expect capital expenditures to grow faster than revenue in FY26.” It was the first time that line had appeared in a Microsoft script in more than a decade. The market barely reacted. The stock ticked up. The halo held.

    Between the fireworks of July 4 and the first snowfall of December, the company delivers four quiet incisions to its most loyal constituencies. Each cut is bandaged with the same phrase—“aligning investment with customer value”—and each is timed for the blind spot of the news cycle: buried in a changelog, stapled to a holiday Friday, whispered beneath a Call of Duty trailer. Together they form a montage of extraction, scored by the hum of ten-thousand GPUs that never sleep.

     

    Four squeezes, one playbook

    None of these moves is catastrophic on its own. The pattern is what matters: when growth normalises and capex spikes, the easiest lever is the captive user.

     

    GitHub Actions: taxing your own metal

    In mid‑December 2025, GitHub published a pricing change that would have introduced per‑minute fees for Actions self‑hosted runners—compute you run on your own electricity, your own metal. The reaction was immediate: developer forums, social feeds, and issue trackers lit up with complaints that the change felt like a toll on captive workflows. GitHub later said the rollout was postponed. Even if the fee never lands, the test matters: when the AI bill rises, Microsoft can trial new toll booths in the places developers can’t easily abandon.

     

    VS Code: deprecate free AI, meter the tab

    In mid‑December 2025, Microsoft signaled that IntelliCode’s individual tier was being deprecated. In plain terms: a long-running free AI assist is being discontinued. For years, developers pressed Tab and got AI help for free. Now the same reflex triggers an upsell: “Try GitHub Copilot—$10/month, 300 completions included.” Hacker News responds with migration scripts—Tabnine, Codeium, open models. A free habit is quietly converted into a meter. Not a scandal. A hairline crack: the halo holds, but the hand now pays to keep typing.

     

    Microsoft 365: Copilot cover for another hike

    On December 4, the third hike in four years lands quietly in IT inboxes—E5 up 16.7 percent, effective July 2026. The justification email arrives like a Christmas card from an ex: “over 1,100 new features, including Copilot integrations.” But Microsoft’s own Work Trend Index suggests Copilot usage is still uneven across eligible seats. The customer backlash is muted but visible: Reddit r/sysadmin fills with screenshots of Google Workspace pilot invites—“We’re tired of the nickel-and-dime.” In the same month, Skype consumer is unplugged—once the largest voice network on Earth, now a line item in a cost-out ledger, its ghost forwarded to Teams.

     

    Game Pass: higher rent, fewer walls

    On October 1, Game Pass Ultimate jumps to $29.99—an extra $120 a year for families already juggling Netflix, Disney+, Spotify. The official framing is predictable: “Reflects the value we’re delivering with Call of Duty day-one.” But the customer backlash is immediate and legible—threads titled “pricing backlash” and “$30 is insane” dominate the week. Then December’s dagger: a Halo remake will launch same‑day, same‑price on PlayStation 5. Reddit declares the quiet part out loud: if the wall is coming down, the rent reads like a tax on loyalty. Not a crisis. Another crack in the armor.

    Four squeezes, one playbook: when the future arrives more slowly than the bill, monetize the moat.

     

    The numbers the halo can’t hide

    The numbers arrive like a second moon—too large to ignore, too quiet to scream.

    • Revenue: $281.7 billion, up 15 percent —a city of money the size of Finland.
    • Azure growth: 33 percent, but the slope is bending (51 → 42 → 33 in thirty‑six months) —the lip still high, the landing already softer.
    • Capex: $62 billion FY25 → guidance >$70 billion FY26; Q1 alone $34.9 billion —a new Nissan factory every week.
    • Free cash flow: flat at $60 billion —the same river as last year, despite the city growing.
    • Cloud gross margin: 66 percent, down a percentage point —a slow leak you only feel when the sea is calm.

     

    Copilot adoption rate 2025

    The headline is “use.” The business model is “paid seats.” Those are not the same metric.

     

    Microsoft says 70 percent of the Fortune 500 “use” Copilot. The revenue metric is colder: < 2 percent of eligible Office seats appear to be paying.

    At $30/user/month, that implies roughly $1.2 billion ARR—small beside a $280 billion empire and short of the $8 billion narrative. Verdict: the PR talks scale; the seats don’t yet agree.

    Layoffs: 15,000+ in three waves—May, June, July—followed by a $4 billion beat.

    Operating margin: +3 percentage points post-cuts.

    Nadella’s internal memo: “The layoffs have been weighing heavily on me.”

    The spreadsheet answers: the machine ran smoother without them—proof of bloat, not transformation.

     

    Game Pass economics

    Game Pass is often framed as the perfect subscription flywheel: recurring revenue, sticky libraries, and a constant drip of “day‑one” moments. But the economics are less magical when the content bill rises and exclusivity stops being exclusive.

    Microsoft hasn’t consistently published a current Game Pass subscriber number in 2025 disclosures, and third‑party estimates vary. The direction still matters: as the catalogue expands (and now carries Call of Duty expectations), the cost base grows faster than the average player’s willingness to pay.

    That makes the $29.99 Ultimate price point read less like “more value” and more like margin protection—especially when marquee releases are no longer locked to Xbox hardware. If Halo can be a day‑one PlayStation headline, the exclusivity premium becomes harder to defend inside a monthly bundle.

    Editorial read: when subscriptions start to feel like rent, the first churn is emotional—people cancel not because they can’t afford it, but because they resent the trade. That resentment is the real warning signal: pricing controversy doesn’t need to crater subscribers overnight to weaken the moat; it just needs to make “value” feel disputed.

     

    Azure deceleration whisper-track

    Azure’s growth arc is still impressive, but the slope is bending—51 percent to 42 percent to 33 percent over three years. Market chatter suggests further deceleration into the high‑20s by early FY26, even as AWS growth holds closer to the low‑30s.

    If Azure slips below 25%, the premium multiple cracks—32× → 22× overnight, a $700 billion haircut.

    Credit-market footnote: as Microsoft’s AI infrastructure spending accelerates, analysts and investors have started asking the obvious question—how quickly does revenue catch up to the build-out? Reporting in 2025 highlighted the scale of Microsoft’s datacenter investment plans (including the role of capital leases) and the sensitivity of the AI trade to any sign of pacing or pullback.

    That doesn’t require a downgrade narrative to matter. It’s enough that the cost base is now big enough to become a story on its own—one that can overwhelm the PR if growth softens.

     

    History does not repeat; it harmonises in a minor key

    IBM (1988–1993) – The Blue Whale’s Last Song

    1988: IBM is the blue whale of enterprise—36 percent share of every datacenter, margins fat as blubber.

    The PC clone tide rises; mainframe sales stall.

    The response: raise maintenance fees 30 percent overnight, sunset the cheaper “basic” tier, force enterprises onto “premium support.”

    Analysts nod—“still dominant.”

    1993: Revenue flatlines at $62 billion, same as 1989.

    January: new CEO Lou Gerstner announces 60,000 layoffs—not a drip, a deluge.

    Stock: $130 → $46 in eighteen months—65 percent of market cap evaporates.

    Gerstner later writes: “We’d been living off legacy cash cows, raising prices faster than value, while the world moved to networks.”

    The whale survives—barely—by abandoning PCs and selling services.

    But the goodwill? Bleached bones on the beach of tech history.

     

    BlackBerry (2010–2013) – The Crack in the Keyboard

    2010: Research In Motion owns the thumbs of the planet—40 million addicts, BIS fees printing cash.

    The iPhone is a toy; Android is a hobby.

    2011: Co-CEO Mike Lazaridis hikes BIS/BES fees 10 percent, kills the Wi-Fi-only PlayBook.

    CNBC clip: “We’re pivoting to software.”

    2012: Revenue down 19 percent to $11 billion—first annual drop ever.

    2013: 4,500 layoffs, $192 million loss, stock $85 → $6—a 95 percent crater.

    The company that invented pocket email becomes a cautionary footnote in someone else’s keynote.

     

    Intel (2018–2024) – The Silicon Crown Rusts

    2018: Intel is the silicon crown—90 percent server share, gross margin 60 percent.

    10-nanometer delays; AMD surges.

    The response: raise Xeon prices 5–8 percent, end perpetual licences, push subscriptions.

    2024: 15,000 layoffs—15 percent of workforce—while capex balloons to $25 billion chasing TSMC.

    Revenue flat, margin 41 percent, stock halved.

    The kingdom that built the digital century becomes a foundry tenant in its own backyard.

     

    Cisco (2001 & 2011–2016) – The Network That Ate Itself

    2001: Dot-com bust; Cisco is the spinal cord of the internet—80 percent router share, margin 53 percent.

    Bandwidth demand collapses.

    The response: raise support contracts 25 percent, end-of-life cheaper ASR routers.

    8,500 layoffs August 2001, 6,000 more by 2003.

    Stock: $80 → $10—88 percent gone.

    2011–2016: SDN threat—white-box switches, Arista, AWS Direct Connect.

    Cisco’s answer? Another round of support hikes, 14,000 cuts, growth from 50% → low single digits.

    The network that once routed every packet becomes a support-invoice engine no one loves.

    All four were “admired” the year before the cliff.

    All blamed “transition.”

    All lost 25–90 percent of market cap inside twenty-four months.

    Microsoft is not the first frog. It is simply the biggest.

     

    The ropes and the forecast

    The “boiling frog” story is more metaphor than lab result, but it captures the risk: when change is gradual, people adapt—until the costs are undeniable.

     

    Microsoft’s ropes today

    • Azure: high switching costs for large enterprises—migration is expensive, slow, and politically risky.
    • Microsoft 365: deeply embedded productivity + compliance plumbing that’s painful to unwind once standardised.
    • Game Pass: a convenience bundle that can become “rent” if value feels disputed.

     

    Water-temperature forecast for 2026

    • Azure: watch whether growth continues to decelerate as AI demand normalises.
    • Copilot: watch whether paid adoption meaningfully catches up to “usage” messaging.
    • Game Pass: watch whether pricing backlash translates into sustained churn or just noise.

    If two of the three deteriorate at once, the market narrative can flip from “AI halo” to “margin defense,” and the squeeze becomes the story.

    The frog will finally see steam; the only question is whether it jumps or croaks louder.

     

    Postcards from the boil

    Imagine New Year’s Eve 2026.

    The datacenter outside Des Moines glows like a city that never sleeps; ten thousand GPUs hum a single note: margin.

    On Slack, a developer in Lagos pastes: “Moved my last repo off GitHub—feels like exhaling.”

    In a WeWork in Warsaw, an IT admin clicks “Export to Google” on fourteen terabytes of SharePoint and feels the same exhale.

    In a living room in Wichita, a father tells his son they’re cancelling Game Pass—Halo is on PlayStation now.

    The water is 47 °C.

    The frog is still quoting the stock price.

     

    FAQ

     

    Why did Microsoft raise prices in 2025–2026?

    Microsoft’s public framing is “more capabilities” and “more value,” often bundled with AI positioning. This pressure isn’t unique to Microsoft. We examined the same collision between rising AI costs and mature SaaS economics in our AI profit boardroom review—the broader backdrop that makes these squeezes feel less like coincidence and more like timing. The editorial lens in this piece is different: when AI infrastructure spending accelerates and growth normalises, pricing becomes the cleanest lever—especially inside locked‑in ecosystems. That doesn’t prove bad faith; it explains why Microsoft price increases in 2025 and the Microsoft 365 price hike for July 2026 can cluster—and why customer backlash is the signal to watch.

     

    What happened with GitHub Actions self-hosted runner pricing?

    GitHub announced a per‑minute fee for Actions self‑hosted runners—compute you run on your own machines. The move sparked a GitHub self‑hosted runners pricing backlash (and a broader GitHub Actions pricing controversy in late 2025), before GitHub said the change was postponed indefinitely—effectively a reversed rollout for now. Even with that rollback, the episode signaled a willingness to test new tolls inside a captive workflow.

     

    What does “extraction” mean in platform businesses?

    In this context, “extraction” is shorthand for shifting from growth-led expansion to monetising users who are already locked into a platform—through pricing changes, reduced free tiers, bundling, or policy shifts. It doesn’t imply illegality; it describes a strategy that can feel like a tax on switching costs.

     

    What is capex, and why does it matter here?

    Capex (capital expenditure) is money spent building long-lived assets—like datacenters and AI infrastructure. When capex rises faster than revenue, the pressure to protect margins increases. One common response is to lean harder on captive ecosystems where small pricing moves can compound into large returns.

     

    What’s the risk of ecosystem lock‑in?

    Lock‑in can be efficient when it reduces complexity and improves reliability. The risk is asymmetry: once exit costs become high, the buyer’s bargaining power falls—making it easier for the vendor to change terms, pricing, or product direction without immediate loss of demand.

     

    How should buyers evaluate Copilot ROI claims?

    Treat broad “usage” claims as a starting point, not proof of value. Buyers can pressure-test ROI by separating pilots from paid adoption, measuring time saved on specific workflows, and tracking whether productivity gains persist after novelty fades. Where possible, compare results to cheaper alternatives and to process improvements that don’t require new licenses.

     


     

    Sources & Notes

    All figures and claims in this editorial should be read alongside their original references. Where exact numbers are cited, sources should be provided as direct links or formal citations below.

     

     

    GitHub Actions pricing and reversal

     

    VS Code / IntelliCode deprecation and Copilot upsell

     

    Microsoft 365 pricing, Copilot usage, and product changes

     

    Game Pass pricing, exclusivity changes, and churn claims

     

    Financials, capex, margins, layoffs, and credit commentary

     

    Method notes

    Ben Rogers Contributor

    Ben Rogers is Head of Growth at VaaSBlock and regular contributor, recognised for building real companies with real revenue in markets full of noise. His work sits at the intersection of growth, credibility, and emerging technology, where clear thinking and disciplined execution matter more than hype. Across his career, Ben has become known as one of the most effective growth operators working in frontier markets today.

    He has scaled technology companies across continents, cultures, and time zones, from Thailand to Korea and Singapore. His leadership has helped transform early-stage products into global growth engines, including taking Travala from 200K to 8M monthly revenue and elevating Flipster into a top-tier derivatives exchange. These results were not the product of viral luck. They came from structured experimentation, high-leverage storytelling, and the ability to translate market psychology into repeatable growth systems.

    As VaaSBlock’s Head of Growth, Ben leads the company’s market strategy, credibility frameworks, and research direction. He co-designed the RMA, a trust and governance standard that evaluates blockchain and emerging-tech organisations. His work bridges operational reality with strategic insight, helping teams navigate sectors where the narrative moves faster than the numbers. Ben writes about market cycles, behavioural incentives, and structural risk, offering a deeper view of how AI, SaaS, and crypto will evolve as capital becomes more disciplined.

    Ben’s approach is shaped by a belief that businesses succeed when they combine clear thinking with practical execution. He works closely with founders, regulators, and institutional teams, advising on go-to-market strategy, credibility building, and sustainable growth models. His writing and research are widely read by operators looking to understand how emerging technology matures.

    Originally from Australia and based in APAC, Ben is part of a global community of builders who want to see technology deliver genuine value. His work continues to shape how companies in emerging markets think about trust, growth, and long-term resilience.