With just seven calendar days left until the 27 June 2025 expiration, traders pounced on short-dated MicroStrategy calls at 382.5-390 strikes. The most notable flow of the bunch is the extremely high volume-to-open interest (V/OI) ratio on the 385 strike call. Daily volume for this contract reached 11,182 against 3,741 open interest, resulting in a V/OI ratio of just under 3. This suggests fresh, aggressive buying interest as the volume far exceeds existing open positions.
The total premium deployed across these four call positions exceeds $9.5 million, with individual trade premiums ranging from $2.1M to $3M. All strikes (390, 385, 382.5) are significantly out-of-the-money relative to the spot prices shown (ranging from $367-376). This indicates bullish bets on substantial upward movement within the week. The trade types include blocks, sweeps, and splits, suggesting institutional participation rather than retail activity. The size of these positions – with individual contracts ranging from 5,000 to 7,411 – combined with the short 7-day timeframe to expiration, indicates either a significant catalyst expectation or hedging activity ahead of a potential announcement or event.
Volume and Open Interest Data
Volume in the MicroStrategy $385 calls expiring 27 June 2025 exploded late this week. On the 20th of June, the contract printed 19,850 contracts against just 3,741 open interest This implies a volume-to-OI ratio of roughly 5.3-to-1. That dwarfs the prior session on June 18th, when 4,150 contracts traded versus 1,221 OI (≈3.4-to-1). Open interest grew by 2,520 contracts over those two days, confirming that a meaningful slice of the Friday burst was fresh upside exposure added with only one week left to expiry.
Despite the heavy demand, the option’s closing price eased from $4.69 on June 18th to $3.32 on June 20th, while implied volatility ticked up to about 45 percent. This implies traders paid up for volatility even as the underlying pulled back. Overall, the sharp jump in OI and the outsized V/OI ratio point to aggressive new bullish positioning in the short-dated $385 strike.
More Notable Options Trades Observed
An additional notable sweep order stood out on MicroStrategy’s tape today. 150 contracts of the 19-Sep-2025 $300 calls were lifted at the ask for $88.20 while the stock sat at $368.16. The trader committed roughly $1.3 million in premium. With 252 total contracts trading on the strike for the day, that block represented about 60% of session volume. Yet, overall volume-to-open-interest sits at just 0.15 (252 vol ÷ 1,655 OI). Meaning, the print is sizable in dollars but not large enough in contract count to overwhelm existing positions.
Because the call is deep in-the-money (≈ $68 intrinsic, ≈ $20 extrinsic) and still has about three months until the 19 September expiry, the buyer likely sought high delta exposure. This would have the option contract behave much like the underlying shares while tying up far less capital. The sweep route underscores urgency to secure fills across venues. This reinforces a bullish read on the flow even though the contract-level V/OI ratio remains modest.
What’s Happening at MicroStrategy
MicroStrategy —now formally doing business as Strategy—has kept its foot on the gas in 2025. On June 16th, the company revealed it bought another 10,100 BTC for roughly $1.05 billion. The purchase lifted its treasury to about 592,100 coins and pushed MSTR shares back toward the $400 level. Just weeks earlier, its Q1 2025 report showed holdings of 553,555 BTC as of April 28th; the successful completion of a record $21 billion at-the-market common-stock program; adoption of fair-value accounting that produced a $12.7 billion uplift to retained earnings; and management’s decision to raise full-year “BTC Yield” and “BTC $ Gain” targets.
To fund the nonstop accumulation, Strategy has layered on fresh capital-raising tools, including a new $2.1 billion Series A Perpetual “Strife” preferred-stock ATM announced in May. It also filed for an additional $1 billion common-stock sale earlier this month, which Executive Chairman Michael Saylor hinted would finance further bitcoin buys. The firm’s swelling BTC war-chest has pushed its market cap past $100 billion. This achievement has earned it seats in major benchmarks like the Russell 1000 and Nasdaq 100. Such inclusions quietly inject bitcoin exposure into broad index funds and, by extension, millions of passive investors. Altogether, the recent cadence of billion-dollar equity raises, outsized bitcoin purchases and rising index weight underscores Strategy’s evolution from software vendor into a leveraged proxy for the world’s largest cryptocurrency.
About MicroStrategy
MicroStrategy is a publicly traded enterprise software company best known for its business intelligence (BI) platform, which helps organizations analyze data to make informed decisions. Its core product offers powerful tools for data analytics, dashboard creation, and reporting, catering to large enterprises across industries.
In recent years, however, MicroStrategy has gained widespread attention for its strategic pivot into Bitcoin. Under the leadership of Executive Chairman Michael Saylor, the company has become one of the largest corporate holders of Bitcoin, using it as a primary treasury reserve asset. This dual identity—enterprise analytics provider and Bitcoin proxy—has made MicroStrategy a unique and closely watched player in both the tech and crypto markets.
Analyst Ratings
| Analyst Source | Rating | Updated |
|---|---|---|
| CFRA | Not Rated (No stars) | 06/07/2025 |
| Market Edge | Long | 04/25/2025 |
| Argus | No data | No data |
| Morningstar | No data | No data |
| LSEG | Outperform | 06/08/2025 |
| Schwab Equity Ratings | F (Lowest Grade) | 06/09/2025 |
The analyst sentiment for MicroStrategy (MSTR) appears mixed and polarized based on the most recent updates. Notably, Market Edge gives the stock a “Long” rating, and LSEG (London Stock Exchange Group) rates it “Outperform”, both indicating positive forward expectations. On the bearish end, Schwab Equity Ratings assigns MSTR an “F” grade, its lowest rating, suggesting poor fundamentals or risk concerns. Meanwhile, CFRA, Argus, and Morningstar have either neutral stances or have not issued updated evaluations.
This divergence underscores the controversial nature of MicroStrategy’s investment thesis, which blends traditional enterprise software with aggressive Bitcoin exposure. Bulls see upside potential through Bitcoin and business growth, while bears flag volatility and balance sheet risk.
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Disclaimer: Options trading involves significant risk and is not suitable for all investors. You may lose the entire investment, and certain strategies may result in losses exceeding the initial amount invested. Past performance does not guarantee future results. This content is for informational purposes only and should not be considered investment advice. Always consult a financial or tax advisor before making investment decisions.
