Strategy Stock at a Critical Juncture: Dividend Hike and Bitcoin Buildup

The shares of Strategy have navigated a volatile period, with their value declining sharply since the summer. The company is now sending a strong message to the market: an increased dividend for its preferred shares and continued aggressive Bitcoin acquisitions, even as the cryptocurrency sector shows tentative signs of stabilization. The pivotal question for investors is whether this dual approach of shareholder returns and Bitcoin leverage can solidify the recent apparent bottom in the stock price.

Concurrently, Strategy is steadfastly advancing its position as a corporate Bitcoin treasury vehicle. In a series of transactions between December 22 and 28, 2025, the company purchased an additional 1,229 Bitcoin. The total outlay for this acquisition was $109 million, resulting in an average purchase price of approximately $88,568 per coin.

This latest buying spree brings the company's total holdings to:
* Roughly 672,497 BTC
* A notional total value of about $50.4 billion (based on recent purchase prices)
* This comes as Bitcoin's price has recovered to trade above $89,254

Despite the sheer scale of these holdings, the stock currently trades at an estimated 20–25% discount to the net asset value (NAV) of its Bitcoin portfolio. This discount persists due to ongoing weakness in the broader crypto market. The company is anticipated to report a significant unrealized loss on its holdings for the fourth quarter, even though the assets remain on the balance sheet. This growing Bitcoin reserve, coupled with a tangible NAV discount, forms a core part of the current investment thesis, as investors can buy the stock for less than the stated value of its underlying cryptocurrency assets.

Dividend Increase Signals Financial Confidence

A key driver behind the recent share price recovery was a board resolution concerning the Variable Rate Series A Perpetual Stretch Preferred Stock (Ticker: STRC). According to an SEC filing dated January 2, 2026, the annualized dividend yield on these preferred shares will be raised from 10.75% to 11.00%.

In practical terms, this translates to a monthly distribution of about $0.917 per preferred share. The record date is set for January 15, 2026, with payment following on January 31. Market participants interpret this move as a signal that the company maintains control over its liquidity and cash flows, despite its ambitious Bitcoin accumulation strategy.

Should investors sell immediately? Or is it worth buying Strategy?

This sentiment provided some relief in the equity price. On Friday, the common stock advanced by 3.43% to close at $157.16. While the share price remains deeply wounded, having been halved over the preceding twelve months, near-term demand appears to be stabilizing.

Analyst Perspectives and an Upcoming MSCI Catalyst

Despite the severe price correction, institutional analysts maintain a constructive outlook. The Benchmark Company has reaffirmed its "Buy" rating and a price target of $705 for 2026. From current levels, this implies a theoretical upside potential of nearly 350%.

TD Cowen also remains optimistic, citing a $500 price target. Their rationale centers on the company's debt being largely secured by its Bitcoin assets rather than stemming from operational losses—a crucial distinction for investors focused on balance sheet health.

However, a near-term event is drawing significant attention. On January 15, MSCI is scheduled to rule on the classification of companies holding substantial digital treasury assets. Estimates suggest a negative decision could trigger forced outflows of approximately $2.8 billion from relevant indices and funds. The stock's recent 3% gain is being viewed by some traders as a bet on a more stabilizing outcome from this review.

Technical Outlook and Key Levels

From a charting perspective, the area around $150 is now viewed as critical near-term support. A hold above this level suggests short-term consolidation, though the stock's 46% decline over the past year and its position more than 40% below the 200-day moving average underscore the severity of the preceding downturn.

On the upside, the zone around $200 now stands as the first significant resistance area. The confluence of a raised preferred dividend, a massive Bitcoin inventory, and a visible NAV discount creates a compelling setup. The stock's future trajectory will likely be determined by two primary factors: the mid-January MSCI classification decision and the price direction of Bitcoin, which currently trading above $89,000 reinforces a recent shift in sentiment on the crypto front.