Microsoft Bears Load Up on Deep ITM Puts as $4.96M Options Bet Targets $535 Strike

By TrendSpider Editor

A single unusual options contract on Microsoft Corporation is drawing attention Monday, with a put purchase carrying a premium of $4,959,000 commanding the spotlight. The contract sits deep in the money relative to MSFT's current price of $508.47, signaling a notable directional bet from at least on

Microsoft Bears Load Up on Deep ITM Puts as $4.96M Options Bet Targets $535 Strike

A single unusual options contract on Microsoft Corporation is drawing attention Monday, with a put purchase carrying a premium of $4,959,000 commanding the spotlight. The contract sits deep in the money relative to MSFT's current price of $508.47, signaling a notable directional bet from at least one sophisticated market participant. With shares trading within a 52-week range of $349.20 to $553.72, the stock sits in the upper half of that band, making this bearish positioning worth watching closely.

Key Drivers of the MSFT Stock Move

• Main Catalyst: A single put contract with a $535 strike expiring January 21, 2028 printed with a premium of $4,959,000, representing 600 contracts against an open interest read of 385% above existing levels, flagging it as a highly unusual and deliberate trade.
• Bull Case: MSFT shares are up 1.70% on the session to $508.47, demonstrating underlying price strength even as this bearish bet was placed. The stock remains well above its 52-week low of $349.20, suggesting the broader trend has favored buyers over the past year.
• Bear Case: The $535 put sits above the current price of $508.47, meaning it is already in the money. A trader paying nearly $5 million in premium for a deep ITM put expiring in January 2028 may be positioning for sustained downside or hedging a large long exposure, either of which reflects caution about where MSFT goes from here.

The forward setup for Microsoft is a balancing act between its strong long-term positioning in cloud and artificial intelligence and the risks that come with a stock trading near the top of its 52-week range. The $535 strike on this put contract represents a level that MSFT has previously traded at, and the long-dated January 2028 expiration gives this trade considerable runway. Whether this is outright speculation or a hedge against an existing long position, the sheer size of the premium deployed suggests conviction. Investors will want to monitor whether additional unusual flow emerges in the coming sessions to determine if this is a one-off print or the beginning of a broader pattern of institutional repositioning.

MSFT Unusual Options Activity

One unusual options contract was flagged on Microsoft today, August 10, 2026. The details are as follows:

• Type: Put | Strike: $535 | Expiry: January 21, 2028 | Volume (Size): 600 contracts | Open Interest: 385% above existing OI | Status: In the Money

The total premium on this single contract block came in at $4,959,000, and it stands as the only unusual contract flagged today, with a total unusual contract count of one. The 385% open interest reading indicates this trade was not simply adding to an established position but rather represents a significant new directional commitment relative to the existing options market structure at this strike and expiration.

MSFT Seasonality

August has historically been a mixed month for large-cap technology stocks, with late-summer trading often characterized by lower volume and headline-driven volatility. A long-dated January 2028 expiration bypasses multiple earnings cycles and seasonal patterns, suggesting the trader behind this put is focused on a multi-quarter thesis rather than a near-term catalyst.

MSFT Relative Performance

Microsoft gained 1.70% on Monday to close at $508.47, a solid session for the stock. The current price places MSFT roughly in the middle-to-upper portion of its 52-week range of $349.20 to $553.72, sitting approximately $45 below its 52-week high. The day's gain reflects relative strength, though the presence of a nearly $5 million in-the-money put trade suggests not all participants are aligned with that bullish near-term momentum.