Strategy Stock Plummets to 4-Month Low: Is Michael Saylor About to Double Down on Bitcoin?

MicroStrategy's stock just hit its lowest point in four months—and all eyes are on whether Michael Saylor will treat this dip as another buying opportunity.

The Bitcoin Bull's Next Move

When traditional equities falter, Saylor historically doubles down on digital gold. The company's stock slide creates precisely the kind of divergence he's built his strategy around: weakening legacy assets against strengthening crypto fundamentals.

Wall Street's predictable panic meets crypto's calculated accumulation. While analysts fret over quarterly earnings, Saylor's playing a multi-year game where the only metric that matters is Bitcoin dominance.

Another day, another chance for traditional finance to underestimate the man who treats volatility like a discount coupon. The real question isn't whether he'll buy—it's how much.

Strategy (formerly MicroStrategy) is once again making headlines – but not for great reasons. The company’s stock fell to its lowest level since April after Michael Saylor announced a policy change that gives the firm more room to issue shares and buy more Bitcoin.

The moves are now sparking debate. Here are the details! 

Stock Hits Four-Month Low

On Tuesday, MSTR closed down 7.43% at $336.57, with another small drop in after-hours trading. The stock has now lost more than 21% in the past month.

The fall came just as Bitcoin slipped from a record $124,000 to $113,000, an 8.6% pullback in a few days. For Strategy, the timing was brutal – a weaker Bitcoin and an upset shareholder base.

The Rule Change That Sparked It

At the center of the selloff is Strategy’s updated Equity ATM Guidance.

Back in July, the company said it WOULD not issue new shares below 2.5 times its net asset value (mNAV), except to cover debt interest or dividends. But this week, Saylor changed things. 

The new guidance allows the company to issue shares even under that 2.5x mark “to pay interest on debt obligations, fund preferred equity dividends, and when otherwise deemed advantageous to the company.”

That single change triggered a wave of frustration among investors.

Investors Call It a Red Flag

The backlash came quickly on X. One user wrote: “Just a couple of weeks ago at the earnings call, it was announced no issuance below 2.5mNAV. Why the change? Promising investors one thing, then changing very soon after, is not a good sign in my opinion.”

I don’t disagree with issuing common stock opportunistically; however this is a real issue for me. Just a couple of weeks ago at the earnings call, it was announced no issuance below 2.5mNAV. Why the change? Promising investors one thing, then changing very soon after, is not a…

Another former shareholder added: “The head of the company said he wouldn’t sell below 2.5 mNAV, so I bought. … And then he sold below mNAV 2.5.”

Some traders, however, took the opposite view. One pointed out bluntly: “He’s literally telling you straight up he’s gonna buy a… TON more BTC.”

Still Buying at the Top

Despite the controversy, Strategy hasn’t slowed down. Just a day earlier, the firm announced another $51 million bitcoin purchase, even as BTC traded at record highs.

The company now holds 629,376 BTC, worth about $71.3 billion. Strategy’s entire identity is tied to Bitcoin and Saylor seems determined to keep doubling down.

A Wider Crypto Selloff

It wasn’t just Strategy in the red. Other crypto-linked stocks also dropped on Tuesday: Galaxy Digital fell 10%, Coinbase slipped nearly 6%, Robinhood lost over 6%, and Bullish and Circle also slid. The Nasdaq Composite closed down 1.46%.