Bitcoin News: Michael Saylor’s Strategy (Nasdaq: MSTR) disclosed in a June 29 filing that it may sell up to $1.25 billion in Bitcoin, framing the move as a “Bitcoin Monetization Program” aimed at boosting liquidity, funding preferred dividends, and servicing debt obligations.

The filing signals a meaningful shift from Saylor’s long-standing accumulation-first strategy, which has been central to the company’s pitch to both institutional and retail investors.

The turning point came on June 27, when Strategy’s mNAV — the ratio of enterprise value to its Bitcoin holdings — fell below 1 for the first time. This level is critical, as the company’s capital model depended on maintaining a premium to its Bitcoin net asset value. That premium enabled Strategy to issue equity and preferred shares to acquire additional BTC at favorable terms. With mNAV at 0.99, that mechanism has effectively lost traction.

Strategy holds approximately $2.55 billion in cash reserves and said Bitcoin sales would occur “from time to time,” depending on market conditions and capital requirements, without committing to a fixed schedule.

In parallel, the company authorized two share repurchase programs of up to $1 billion each—one for its Class A common stock and another for its Digital Credit Securities, including preferred series STRK, STRF, and STRD.

Pressure is most acute within the preferred structure. STRK carries an 8% dividend on roughly $584 million raised, while STRF offers a 10% yield that can rise to 18% if payments are deferred, based on $711 million raised. The latest issuance, STRD, generated approximately $979.7 million at a 10% non-cumulative rate.

Combined, these instruments create more than $700 million in annual dividend obligations. When Bitcoin traded near $125,000 and mNAV remained above 1, these costs were easily covered through new equity issuance. With BTC now around $60,000 and mNAV below 1, that approach has become significantly more constrained.

Strategy has already made a small move in this direction. On June 1, it sold 32 BTC for about $2.5 million to fund preferred payouts. The latest filing, however, expands the potential scale of sales substantially.

Recent market conditions have compounded the pressure. Bitcoin fell to roughly $58,000 last week amid about $3 billion in outflows, while MSTR shares declined sharply, compressing the company’s NAV buffer. Although BTC has since recovered to around $60,000, it remains well below levels that previously supported Strategy’s model, with options positioning around that level contributing to continued volatility.

Critics were quick to respond. Peter Schiff described Strategy as “now a Bitcoin seller,” highlighting the contrast with Saylor’s earlier stance that BTC should never be sold. While pointed, the criticism reflects a broader structural dynamic: Strategy’s aggressive accumulation acted as a form of price support, which can reverse if selling increases.

The company has rejected suggestions of a strategic pivot, reiterating that Bitcoin remains its primary treasury reserve asset and emphasizing that the move is about liquidity management, not long-term conviction.

The board has also adopted a policy requiring at least 12 months of reserve coverage for preferred dividends and interest obligations, signaling a shift toward stricter balance-sheet discipline and acknowledging reduced reliance on continuous market access.

MSTR shares were trading at $82.31 at the time of writing, down 3.5% on the day and significantly below prior highs reached when Bitcoin approached $125,000. The divergence underscores a key reality: MSTR has functioned not just as a Bitcoin proxy, but as a leveraged bet on mNAV remaining above 1—an assumption that no longer holds.

Bitcoin News: MSTR Outlook — Testing Key Support

Currently near $92, MSTR is holding just above a psychological support level around $90. A break below that threshold could accelerate selling pressure, particularly from investors who previously viewed the stock as a premium Bitcoin vehicle. With that premium now eroded, the equity offers neither direct BTC exposure nor the stability of a cash-generating business.

The dual $1 billion buyback programs provide a potential stabilizing tool for both common and preferred shares. If deployed aggressively, they could help establish a near-term floor.

However, authorization does not ensure execution. The company’s immediate priority remains meeting preferred dividend obligations, limiting flexibility for capital returns.

In the near term, MSTR is likely to trade in a range of $80 to $89, with direction closely tied to Bitcoin’s trajectory. A move above $63,000 could push mNAV back above 1 and reopen the equity issuance channel. Conversely, a decline toward $55,000 may force larger Bitcoin sales beyond the current $1.25 billion authorization and trigger further repricing across its preferred securities.

Meanwhile, El Salvador continues accumulating Bitcoin despite external pressures, highlighting that not all large BTC holders face the same structural constraints as Strategy.

The next key signal will be whether Strategy executes a meaningful Bitcoin sale in the near term and how markets—particularly its preferred securities—respond.