Strategy prepares for $120M stress test as dividends come due in December

Strategy’s playbook may be further tested in the coming months, as its preferred share revenues come due. The recent BTC downturn is pressuring Strategy’s “infinite money glitch.” 

Strategy will face its first big wave of dividends due toward the end of the year, when about $120M is due on several of its preferred stocks. Strategy reported just $54M in its cash reserves for Q3, meaning it may have to use a part of the proceeds from Euro-denominated STRE preferred shares.

For now, Strategy is liquid, despite using some of its funds for dividends and not new BTC purchases. 

If $BTC drops to our $74K average cost basis, we still have 5.9x assets to convertible debt, which we refer to as the BTC Rating of our debt. At $25K BTC, it would be 2.0x.

— Strategy (@Strategy) November 25, 2025

Strategy’s “infinite money glitch,” which worked during BTC expansion, is now unwinding and showing a potential weakness. The bigger test for MSTR will be the MSCI review in mid-January, which may lead to selling pressure as funds unwind their positions. 

In total, over $9B of MSTR shares are held by passive funds. A removal from indexes may cause $2.8B in almost immediate sales, and more in the coming months. 

What can Strategy do next?

Strategy retains 649,870 BTC, with most identified through on-chain wallets. Even with a low MSTR price, the treasury is not in danger. 

The company may continue its regular consulting and knowledge product operations while pausing BTC purchases. Some of the preferred shares may have their dividends delayed to decrease the cash burden. If Strategy wants to keep raising funds despite everything, it may have to resort to the STRC preferred shares, raising the promised dividend, and making its playbook even more expensive.

In 2025, Strategy has no BTC-backed loans, threatening the need for liquidation. The BTC have no risk exposure, but they are also not considered valuable by MSTR holders, who do not actually have a claim on the coins. 

MSTR can only be valuable if BTC starts another rally, making the playbook viable again. In general, MSTR is considered a tool to amplify BTC trends. MSTR recovered slightly to $172.19, after dipping to a local low of $166. 

Strategy is still unable to buy the dip

The current stock level means Strategy is unable to “buy the dip,” and instead has been exposed to BTC prices during rallies and near all-time peaks. For now, Strategy’s breakeven is just above $74,000, and the company has hinted at possibly selling some of the BTC to service its obligations. 

Strategy has some leeway on its $8B in convertible debt, most of which is already out of the money. The maturity dates of this debt are still years away, but creditors may already show impatience with the company’s ability to repay. 

Strategy generates limited free cash, instead relying on new raises for liquidity. For Strategy, the only hope is another BTC bull cycle as its debt matures, which may also save the MSTR price. 

The debt will start maturing between 2028 and 2032, potentially creating a scenario of rapidly selling BTC to cover the obligations. In the interim, Strategy will have to service $700M in annual dividend obligations while waiting for an eventual BTC recovery. 

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