Strategy (MSTR), formerly MicroStrategy, shares have taken investors on a volatile ride, plummeting 40% over the past six months as Bitcoin (BTCUSD) price swings and concerns about the company’s aggressive fundraising strategy weigh on the stock.

The software company, which has transformed itself into the world’s largest corporate holder of Bitcoin, saw its shares hit a seven-month low this week after the cryptocurrency briefly dipped below $100,000.

What was once a winning bet during the crypto boom has turned sour as investors question whether Chairman Michael Saylor’s strategy of continually buying more Bitcoin makes sense at current prices.

The sale of Strategy’s preferred shares has raised concerns about shareholder dilution, while the premium investors once paid for MSTR shares over their Bitcoin holdings has been sharply reduced.

Let’s see if you should buy, sell or hold MSTR stock right now.

Michael Saylor’s bold Bitcoin strategy faces its toughest test yet as investor enthusiasm cools and the company struggles to maintain momentum. Over the past five years, Strategy has evolved from a modest software company to become the world’s largest corporate holder of Bitcoin.

Strategy recently announced that it will increase its preferred stock dividend to 10.5% in November. The move comes as the company tries to revive sluggish demand for these securities, which have become its main source of funding to buy more Bitcoin.

MSTR shares have fallen roughly 45% since their November high as the premium it once enjoyed over its Bitcoin holdings has narrowed dramatically. Its market-to-net asset value multiple has fallen to 1.06 times from 2.7 times last year and is near a 20-month low. This decline makes the issuance of new common stock dilutive to existing shareholders, forcing the company to consider alternative financing options.

Although BTC recently hit an all-time high, it is down 20% from record levels. In the third quarter of 2025, Strategy reported net income of $2.8 billion tied to unrealized gains on its crypto stock, valued at $70 billion. A few days ago, Strategy added 487 Bitcoin using “only” $50 million of preferred stock sales, a far cry from the multibillion-dollar purchases that once moved the markets.

In particular, Strategy will no longer issue common stock below 2.5 times its net asset value, except to cover interest and dividend payments, which total $689 million annually. However, with its premium hovering just above 1.0x, this threshold seems restrictive.

Strategy is now exploring international markets and considering ETFs backed by its preferred shares. It also plans to launch its first euro-denominated preferred stock, with $715 million in proceeds.

Investors should gain exposure to MSTR stock in November 2025 if they are bullish on Bitcoin. BTC prices increased more than 7 times between January 2023 and October 2025. During this period, MSTR shares increased 30 times.

Out of 15 analysts covering MSTR stock, 12 recommend “Strong Buy”, one recommends “Moderate Buy”, one recommends “Hold” and one recommends “Strong Sell”. The average price target for MSTR stock is around $523, indicating a potential upside of more than 120% from current levels.

As of the date of publication, Aditya Raghunath had no positions (either directly or indirectly) in any of the securities mentioned in this article. All information and data in this article is for informational purposes only. This article was originally published on Barchart.com