Date: November 24, 2025
Bitcoin is limping through one of its ugliest months in years, and no listed company is more exposed than MicroStrategy – now rebranded simply as Strategy but still trading under the ticker MSTR. As BTC trades in the mid‑$80,000s after a brutal 30%+ slide from October’s all‑time high, Strategy’s giant bitcoin bet is almost back to breakeven, its stock is having its second‑worst month since adopting a “Bitcoin standard,” and investors are suddenly obsessing over three things:
- A looming $6.6 billion wall of convertible debt
- A $1 billion 2027 “put” option that could force cash repayment
- Fresh MSCI index–exclusion risk that might trigger billions in forced selling
Here’s what’s happening today, how it ties back to recent deep‑dives from Barron’s, Investor’s Business Daily and CoinDesk, and what MSTR investors and bitcoin traders are watching next.
Bitcoin price today: Fear still dominates after a “black November”
Bitcoin started Monday, November 24, on the back foot again. After briefly bouncing over the weekend, BTC dipped below $86,000, leaving it roughly 30–32% below October’s peak near $126,000. [1]
Across the day, major crypto market wraps describe:
- BTC trading in a tight but shaky $80,000–$90,000 range, with analysts warning that rejection near the upper end could open a slide toward the low‑$80Ks. [2]
- Market structure called “fragile,” with many desks expecting consolidation between roughly $85,000 and $90,000 as traders wait for clearer signals from the Federal Reserve and macro data. [3]
- Some strategists now openly floating downside targets as low as $50,000 in 2026 if ETF outflows and macro headwinds persist. [4]
Sentiment across crypto is firmly in the “fear” zone, with altcoins underperforming while BTC grinds sideways around the mid‑$80Ks. [5]
That backdrop is critical for understanding Strategy’s situation: its balance sheet and stock price are now levered almost entirely to whatever bitcoin does next.
Strategy’s bitcoin hoard: Huge, still profitable – but uncomfortably close to breakeven
Depending on which recent disclosure or analyst note you look at, Strategy now holds roughly 640,000–650,000 BTC, making it by far the largest corporate holder of bitcoin. Estimates from Mizuho and CoinDesk put the stash around 640k–642k coins, while other coverage citing more recent purchases pushes that figure closer to 650k BTC. [6]
Key points:
- At current prices near $86,000, that stack is worth roughly $55 billion.
- After more than five years of accumulation, CoinDesk calculates that Strategy’s overall breakeven level is around $74,400 per bitcoin – the price at which its BTC position would flip from profit to loss on paper. [7]
- The recent crash has brought BTC close enough to that line that Strategy is “barely ahead” on the bet, but still not yet underwater overall. [8]
Crucially, neither Strategy’s lenders nor its preferred‑share investors can force an immediate liquidation just because BTC trades below that $74,400 number. Multiple analyses emphasize that there is no margin call trigger tied directly to the spot bitcoin price; the real pressure points are elsewhere in the capital structure. [9]
From darling to drawdown: MSTR stock is having one of its worst months ever
While bitcoin is down roughly a third from its peak, Strategy’s shareholders have it worse:
- Since July, MSTR has logged negative returns for five straight months, and November 2025 is shaping up to be its second‑worst month since the firm started its BTC strategy. [10]
- Recent coverage notes that MSTR has dropped about 60–70% from last year’s highs, even as BTC is “only” down a bit over 30% from its October top. [11]
- Strategy’s own metrics page shows MSTR trading around $170.50, with a 3‑month drawdown near 50% and a 1‑year return around –57%. [12]
Today, November 24, fresh headlines describe:
- Seven consecutive weeks of declines, with the stock off roughly 14–15% in the past week alone. [13]
- Some major institutions quietly selling an estimated $5.4 billion of MSTR exposure in recent months as they move from using the stock as a bitcoin proxy to holding direct BTC or regulated crypto products instead. [14]
Despite the carnage, several analyses stress that, on a long‑term basis, Strategy’s bitcoin performance still beats most “Big Tech” names – but that’s cold comfort to anyone who bought near the top. [15]
The $6.6 billion problem: Strategy’s convertible debt and the 2027 “put”
The single biggest new worry for investors is convertible debt.
According to Investor’s Business Daily and follow‑up analysis, Strategy faces: [16]
- About $6.6 billion of convertible notes coming due through 2028
- A key $1 billion 0.625% convertible senior note whose first put option date is September 15, 2027
- The notes were originally structured when MSTR traded around $130.85, with a conversion price about $183.19. At today’s ~$170, bondholders have little incentive to convert into stock, which makes cash repayment in 2027 the base case if prices don’t recover. [17]
Analysts warn that unless:
- MSTR’s share price climbs well above $183, or
- Strategy can cheaply refinance its convertibles,
the firm may need to raise new capital or selectively sell bitcoin to meet that 2027 obligation. One widely cited model even estimates that avoiding BTC sales might require MSTR above roughly $183 a share, which corresponds to bitcoin somewhere in the low‑$90,000s by that point. [18]
Additional red flags from recent coverage:
- S&P Global cut Strategy’s credit rating to B‑ in October, citing rising liquidity risk if BTC stays depressed and convertibles remain out of the money. [19]
- If low‑coupon convertibles are replaced with higher‑rate debt while the company also shoulders rich preferred‑share dividends, annual interest + dividend costs could approach $2 billion by 2029. [20]
This is the “debt wall” that both Investor’s Business Daily and CoinDesk say investors can’t ignore, even if the balance sheet looks fine today. [21]
Barron’s: Common stock is “scary,” but preferreds look tempting
Barron’s devoted not one but two in‑depth pieces to Strategy’s capital structure this month – one on preferred shares and one on convertible bonds. [22]
1. High‑yield perpetual preferreds
In “Strategy Stock Is Scary. Its Preferred Might Be Worth a Look,” Barron’s notes that: [23]
- Bitcoin’s ~30% drop since October has cut Strategy’s common stock by more than half, to around the high‑$170s at the time of writing.
- The company has leaned heavily on perpetual preferred stock to fund BTC purchases, issuing multiple series:
- STRK (“Strike”) – ~8% fixed dividend, convertible into common at a very high strike price
- STRF (“Strife”) – 10% fixed, non‑cumulative, and senior in the preference stack
- STRD (“Stride”) – 10% cumulative, but junior to STRF
- STRC (“Stretch”) – launched in August with a 10.5% cumulative coupon, initially priced at $90
- As of late last week, STRK and STRD were trading well below their issue prices, implying double‑digit yields between roughly 11% and 15%, while STRF remained slightly above par, reflecting its seniority. [24]
For income‑focused investors willing to stomach crypto risk, these preferreds now yield far more than typical bank preferreds (around 6%), but they sit behind nearly all of the company’s debt and remain heavily exposed to bitcoin volatility. [25]
2. Convertible bonds now yielding close to 8%
Barron’s companion piece on Strategy’s convertible bonds highlights that some of the company’s debt – once seen as ultra‑cheap funding – now trades at yields approaching 8%, a clear sign that bondholders are demanding higher compensation for risk. [26]
Together, these articles paint a picture of a layered, highly levered capital stack where:
- Common shareholders absorb the most volatility
- Preferred holders collect big coupons but risk cuts if things get tight
- Convertible noteholders hold the real leverage in 2027 and beyond
CoinDesk: Near breakeven on BTC – but the key test is 18 months away
CoinDesk’s deep‑dive, “Bitcoin’s Plunge Brings Strategy’s Holdings to Near Breakeven, but Key Test Lies 18 Months Ahead,” ties everything together. [27]
Its core messages:
- No near‑term solvency crisis: Even with bitcoin’s plunge, Strategy’s balance sheet isn’t on the brink. The company still has substantial unlevered BTC, and there are no immediate margin calls.
- Real pressure starts in mid‑2027: The September 15, 2027 put option on that $1 billion convertible note is the first real stress test. If MSTR and BTC are still depressed, Strategy may need to:
- Issue more common stock
- Sell a slice of its BTC
- Or restructure debt on less favorable terms
- Preferreds are a double‑edged sword: Some series (like STRF and STRC) still trade around or above issue, but others (STRK, STRD) have dropped sharply, suggesting the market is already demanding a payoff for taking on that risk. [28]
CoinDesk concludes that management has multiple levers to pull to keep paying its preferred dividends and servicing debt – but any of those steps (forced equity issuance, BTC sales, etc.) would likely slam investor confidence and make future capital raising much harder. [29]
TODAY’S twist: MSCI index threat and a fresh $835M bitcoin buy
What makes November 24, 2025 particularly tense is that all of the structural issues above are now colliding with index‑provider and institutional‑flow risks.
1. MSCI may kick “digital asset treasury companies” out of its indexes
FXEmpire, Bitget and other outlets report that MSCI has launched a consultation on excluding “digital asset treasury companies” like Strategy from its global equity benchmarks. [30]
Key details:
- The consultation runs through December 31, with a final decision expected on January 15, 2026. [31]
- Several analyses estimate that removal from key MSCI indexes could trigger as much as $8–9 billion in passive outflows as index funds and ETFs are forced to sell MSTR. [32]
- Strategy is already not a member of the S&P 500, despite years of trying; now it faces the opposite problem in MSCI’s universe: possible expulsion rather than inclusion. [33]
Bitcoin‑bull investors see this as political and structural risk, not just price volatility. Michael Saylor has publicly shrugged off the concerns, with bitcoin‑friendly outlets quoting him as saying the company remains “indestructible” and that he “won’t back down,” even as the stock slides and some in the community call to boycott banks raising those concerns. [34]
2. Strategy keeps buying the dip – including 8,178 BTC last week
Even as index pressure builds, Strategy has continued to buy more bitcoin:
- Around November 17, the company disclosed the purchase of 8,178 BTC for about $835.6 million, at an average price just above $102,000, according to Barron’s, TradingView and CoinCentral. [35]
- Earlier in November it also added around 487 BTC (~$50 million) using proceeds from its newer high‑yield preferreds (particularly STRC and STRF). [36]
Reports published today say:
- MSTR fell another ~3% as traders digested news of that $835M “buy‑the‑dip” and MSCI’s consultation simultaneously. [37]
- Some coverage suggests Wall Street desks are reducing MSTR holdings, arguing that with spot BTC ETFs and more regulated crypto offerings now available, investors no longer need a leveraged corporate proxy to gain exposure. [38]
A fresh Barron’s note out today underscores how closely the market now watches Strategy’s weekly BTC disclosures. The company has historically been a “steady buyer” every week, and the article warns that any sign of a pause – forced or voluntary – would be a big sentiment shock for both MSTR and bitcoin. [39]
So… is Strategy actually in trouble?
Put bluntly: not today, but the risk profile has changed.
Recent analyses from IBD, Barron’s, CoinDesk and others all land on a similar conclusion: [40]
What looks okay in November 2025…
- Strategy’s bitcoin stack is still in profit overall, even after the crash.
- There is no immediate margin call tied to BTC dipping into the low‑$80Ks or even the high‑$70Ks.
- The company has multiple funding levers – preferred stock issuance, at‑the‑market common stock sales, and, in extremis, small BTC sales – to cover interest and dividend obligations.
…could become a real test by 2027–2028 if:
- Bitcoin fails to reclaim or exceed prior highs before the 2027 put date.
- MSTR’s share price remains below key conversion levels (around $183 for that 0.625% note).
- MSCI or other index providers push ahead with exclusions, forcing large passive investors to dump the stock.
- Higher interest rates and rich preferred coupons push total annual cash obligations toward $2 billion by the end of the decade.
Some analysts even warn that if bitcoin stagnates or falls further, Strategy might eventually have to consider “partial liquidation” of its BTC stash late in the decade to manage debt – a scenario that would be both symbolically and financially painful for a company built on the slogan “We’re never selling.” [41]
What this means for investors and traders (not financial advice)
For people following MSTR, BTC or both, here are the big takeaways as of November 24, 2025:
- Bitcoin price remains the ultimate driver.
- Short‑term, BTC is stuck in a fragile range around the mid‑$80Ks, with analysts split between a bounce back toward $100K and a deeper flush toward $70K–$75K or even $50K over the next year. [42]
- MSTR is now a leveraged, path‑dependent bet.
- You’re no longer just betting on “number go up.” You’re betting that bitcoin rises enough, fast enough to keep ahead of rising interest, rich preferred dividends, and that looming 2027 put.
- Preferreds vs. common vs. bonds are very different bets.
- Common stock (MSTR): Maximum upside if BTC moons again, but takes the first hit from index removals, dilution and sentiment shifts.
- Preferreds (STRC, STRD, STRF, STRK): Double‑digit yields but real risk of dividend cuts in a severe downturn.
- Convertible notes: Currently priced to reflect a meaningful risk premium, but sit higher in the capital stack and get first call on cash flows in stress scenarios. [43]
- Index decisions could be the next big catalyst.
- The MSCI consultation ending December 31 and the January 15 decision date are now circled on every MSTR holder’s calendar. A negative ruling could mechanically increase selling pressure, regardless of whether bitcoin has already stabilized. [44]
- Macro still matters.
- Bitcoin’s November crash has coincided with equity volatility, rising concerns about rate cuts being delayed and large outflows from digital‑asset funds – not just crypto‑specific news. [45]
As always, this is not investment advice. Anyone considering exposure to bitcoin, MSTR, or Strategy’s preferred and debt securities should weigh:
- Their time horizon
- Their tolerance for volatility and drawdowns
- The risk that even a fundamentally sound balance sheet can come under extreme pressure in a high‑leverage, sentiment‑driven asset class like crypto
But one thing is clear after today: November 24, 2025 marks a turning point in how the market thinks about MicroStrategy/Strategy. The story is no longer just “a bold bitcoin bet.” It’s now about whether a highly engineered capital stack can survive a long, messy crypto downturn without being forced to break its own “never sell” promise.
References
1. www.bloomberg.com, 2. www.bloomberg.com, 3. www.theblock.co, 4. www.dlnews.com, 5. www.coindesk.com, 6. finviz.com, 7. www.coindesk.com, 8. www.coindesk.com, 9. www.coindesk.com, 10. www.mexc.com, 11. www.benzinga.com, 12. www.strategy.com, 13. stocktwits.com, 14. coinpedia.org, 15. www.tipranks.com, 16. www.investors.com, 17. www.indexbox.io, 18. www.bitget.com, 19. www.investors.com, 20. www.investors.com, 21. www.investors.com, 22. www.barrons.com, 23. www.barrons.com, 24. www.indexbox.io, 25. www.barrons.com, 26. www.barrons.com, 27. www.coindesk.com, 28. www.coindesk.com, 29. www.coindesk.com, 30. www.fxempire.com, 31. www.bitget.com, 32. blockonomi.com, 33. www.barrons.com, 34. www.investopedia.com, 35. www.barrons.com, 36. www.coindesk.com, 37. coincentral.com, 38. www.markets.com, 39. www.barrons.com, 40. www.investors.com, 41. www.bitget.com, 42. www.theblock.co, 43. www.barrons.com, 44. www.bitget.com, 45. www.coindesk.com
