JPMorgan is urging Strategy to build up its dollar reserves and win back investor confidence after the company's first Bitcoin sale since 2022. At the same time, the analysts are shifting their overall assessment of digital assets from "overweight" to "cautious."
Strategy, formerly MicroStrategy, is a publicly listed US company that has accumulated Bitcoin as its primary treasury asset since 2020 and gears its capital raising toward acquiring more BTC. The business model rests on issuing shares and preferred stock, with the proceeds flowing directly into Bitcoin. Originally, this construction, marketed as a "digital capital markets structure," counted as an innovative model, yet it now faces criticism over its financing viability. With 843,706 BTC, the company holds the largest Bitcoin position of any publicly listed firm, at a total cost basis of around USD 63.8 billion. CEO Michael Saylor had consistently tied the strategy to the principle of "no Bitcoin sales" until early 2026. Now the market is turning against him.
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32 Bitcoin, 2.5 million USD: Strategy's first sale since 2022
In late May 2026, Strategy sold 32 Bitcoin at an average price of USD 77,135, generating proceeds of around USD 2.5 million. The company disclosed the transaction on June 1 through an 8-K filing and stated the purpose as the dividend payment on the STRC Perpetual Preferred Stock. The previous sale had taken place in December 2022 and served tax-loss harvesting at the time. Measured against the total holdings, the 32 BTC amount to just 0.004 percent of the position.
Economically, the sale is therefore barely relevant, yet symbolically it marks a break. For years, Saylor had geared his model toward pure accumulation, which is why any disposal counts as a departure from the core principle. JPMorgan describes the step as "symbolic and voluntary," a demonstration of commitment and flexibility toward the preferred shareholders, but nonetheless characterizes the market impact as "spooked."
The reaction confirmed this reading. Bitcoin fell to a two-month low of around USD 71,000 after the announcement, while the MSTR share lost around 5 percent on the day of the disclosure. Furthermore, US Bitcoin ETFs recorded sustained net outflows across several trading sessions in the following weeks. Bitcoin currently trades at a multi-month low of around USD 63,000.
JPMorgan warns of structural risk in Strategy's dividends
Strategy's capital structure comprises several classes of preferred stock such as STRC and STRK with fixed dividend obligations that total around USD 1.7 billion per year. To service these payments, the company set up a USD reserve position of USD 1.44 billion in December 2025, which was also meant to cover interest on outstanding debt. According to JPMorgan, however, the current reserves now cover only around 6.3 months of dividends. The STRC preferred stock carries a dividend rate of 11.5 percent and recently traded at around USD 94.60, thus below the par value of USD 100. This constellation feeds the concern that the obligations become hard to finance without further Bitcoin sales.
This is exactly where the demand from the analysts under Managing Director Nikolaos Panigirtzoglou comes in. A rebuild of the dollar reserves could be necessary to restore confidence and dispel the concern that Strategy would have to sell more Bitcoin to cover the dividends, they write in the report. Benchmark analyst Mark Palmer, by contrast, sees the BTC holdings as a "viable backstop" for the dividend payments, which shifts the company's risk model. This juxtaposition reveals the core question of the debate: whether the Bitcoin holdings represent sufficient security, or whether they would first have to be liquidated through sales. Moreover, Saylor's shift in communication since the first quarter of 2026 underpins the discussion, because in the Q1 results he placed a more flexible capital allocation in place of the previous "never sell."
JPMorgan still expects 32 billion USD in Bitcoin purchases in 2026
Despite the more cautious tone, JPMorgan is raising its purchase forecast for Strategy. Extrapolating the current year's pace so far, the company is likely to acquire Bitcoin worth around USD 32 billion in 2026. Furthermore, the analysts revised this estimate upward from USD 30 billion compared with the previous month. For comparison, annual purchases in 2024 and 2025 stood at around USD 22 billion each, which points to a structurally growing accumulation pace. The forecast therefore stands in tension with the concern over reserve coverage expressed at the same time.
Saylor himself already signaled the next step publicly. In early June, he hinted at a further purchase via X with the remark "A good time to add more dots." A day later, a shareholder vote was scheduled at Strategy that, among other things, concerned switching the STRC dividend from a monthly to a twice-monthly payout.
Digital assets under broad pressure: JPMorgan's wider picture
The shift in sentiment reaches beyond Strategy. As recently as February 2026, the same analysts had rated digital assets as "overweight" and "positive," whereas the assessment now reads "cautious." At the same time, capital flows have halved. JPMorgan puts inflows since the start of the year at around USD 22 billion, annualized around USD 52 billion and thus about half the prior-year level. This estimate factors in crypto fund flows, CME futures positioning, VC fundraising and corporate treasury purchases, which also include Strategy's acquisitions. Moreover, the bank now puts the chance of the Digital Asset Market Clarity Act 2026 passing at under 50 percent.
The Clarity Act had cleared the markup phase in the Senate Banking Committee on May 14 and still counted as support for institutional inflows in the February report. However, JPMorgan now points to the approaching US midterm elections, the ongoing debate over stablecoin yields and remaining legislative hurdles. These factors thus push regulatory clarity further back.
The macro backdrop also remains fragile. JPMorgan puts Bitcoin production costs, which stood at USD 90,000 at the start of the year, at USD 77,000 at one point and most recently at around USD 87,000, with Bitcoin trading below that for most of the year. Historically, the bank views these costs as a "soft floor" for the price. Furthermore, the "debasement trade" is weakening. The narrative of Bitcoin as an inflation hedge is cooling, according to the analysts, which further reduces its institutional appeal. For altcoins and Ethereum, JPMorgan likewise sees little room to outperform Bitcoin without stronger network activity.
