Strategy escapes crisis signal despite heavy hedging, Anchorage says

Strategy’s options market has remained below historical crisis levels even as defensive Bitcoin positioning has climbed into the top fifth of historical readings, according to new research from Anchorage Digital.

According to a June 25 report by Anchorage Digital head of research David Lawant, traders across Bitcoin options, BlackRock’s iShares Bitcoin Trust (IBIT), and Strategy (MSTR) continue to pay a premium for downside protection, yet Strategy’s options market is not signaling fears of a severe company-specific breakdown.

The research examined options activity on Deribit alongside IBIT and MSTR, arguing that the combination offers a more complete picture of sentiment across crypto-native participants, institutions, and retail investors than any single market on its own.

The Put skew remained elevated in both Deribit and IBIT options, indicating that investors have preferred hedging against losses instead of chasing additional upside. According to the report, defensive positioning ranked in the 82nd percentile of IBIT’s history and the 84th percentile of Deribit’s five-year record.

Lawant also found that Bitcoin options have spent nearly half of 2026 pricing one-week implied volatility above one-month implied volatility. The report attributed the unusual pattern to repeated macroeconomic events, geopolitical developments, and crypto-specific catalysts that have kept traders focused on immediate uncertainty.

Lawant wrote that a return to one-month implied volatility trading above one-week levels would suggest investors are becoming more comfortable looking beyond current risks.

Strategy options remain below historical stress levels

Although Strategy has come under growing pressure in recent weeks, Anchorage Digital said its options market has not reached the conditions that accompanied previous periods of severe market stress.

According to the report, traders continue to buy downside protection, but put skew has not climbed to levels that typically signal expectations of forced deleveraging or a broader crisis surrounding the company.

The assessment comes as Strategy’s capital structure has faced fresh strain. The company’s perpetual preferred stock, STRC, dropped to $82.53 on June 22, about 17% below its $100 par value, before recovering after Strategy disclosed that it had increased its fiat reserves to $1.3 billion. By Thursday, STRC was trading near $75, leaving it roughly 25% below par.

Pressure has also spread to the company’s common stock. Yahoo Finance data showed MSTR shares were trading around $85 on Thursday after falling about 78% over the past year and reaching a fresh 52-week low.

Legal scrutiny has intensified alongside stock weakness

Outside the options market, Strategy has encountered increasing legal and investor scrutiny.

Rosen Law Firm recently announced that it is investigating whether the company made materially inaccurate business disclosures. The firm said it is evaluating potential securities claims and considering a possible class action on behalf of shareholders who suffered losses.

The investigation followed public comments from Bitcoin critic Peter Schiff, who argued that investors in Strategy’s STRC preferred shares could have legal grounds to pursue claims if they purchased the security based on Michael Saylor’s promotion of the company’s Bitcoin treasury strategy. Schiff made those remarks before any law firm publicly disclosed an investigation into potential shareholder claims.

Adding to investor attention, Strategy director Jarrod Patten recently sold another 1,500 MSTR shares as the stock continued its decline.

Despite those developments, Anchorage Digital’s analysis indicates that options traders are preparing for additional volatility rather than pricing in a severe breakdown.

Strategy, led by Executive Chairman Michael Saylor, remains the world’s largest corporate holder of Bitcoin with 847,363 BTC on its balance sheet after pioneering the corporate Bitcoin treasury model in 2020.