has become embroiled in a dispute over the timing of Strategy's (MSTR) sale announcement, which sent shares down nearly 6% and pushed Bitcoin below $71,500 on Monday.
The business intelligence software company formerly known as , one of the largest corporate Bitcoin (BTC) holders, revealed in a 1 Jun filing with the US that it sold 32 BTC between 26 and 31 May to help fund dividend obligations.
However, the sale occurred before the 31 May expiry of a high- contract on events-market firm Polymarket regarding when such a sale would occur, and was disclosed only after the contract's expiry.
Disclosure timing sparks fight
Decentralized prediction market Polymarket saw a contract with more than $130mn in trading volume descend into controversy in the wake of Strategy's disclosure. Strategy's BTC sales, worth roughly $2.5mn, were its first since December 2022.
Supporters of a "Yes" resolution of the Polymarket contract argue the SEC filing confirms the sale happened within the contract period and the outcome should reflect that reality. Polymarket initially resolved the market as "No", citing the absence of public confirmation during the market's active period.
According to a notice attached to the contract, Polymarket said: "No information from MSTR, data, or consensus of credible reporting confirmed that MicroStrategy [sic] sold Bitcoin within the market's timeframe. Confirmation achieved outside of the market's time frame does not qualify."
The market has since been challenged twice and remains under review. If no consensus is reached, the dispute is expected to escalate to a vote by holders of UMA's . UMA is a decentralized oracle designed to provide verifiable data for and serves as the final arbiter for contested Polymarket outcomes.
Prediction market growing pains
This episode exposes a broader challenge facing as they expand into increasingly specific corporate and financial events. Unlike election results or sporting outcomes, corporate disclosures can occur days after the underlying event. This creates ambiguity over whether contracts should be judged by when the event occurred or when it became publicly verifiable.
Similar timing disputes have arisen before, including a 2025 Polymarket market on a Ukraine mineral deal that drew criticism over UMA tokenholder voting influence. The current dispute comes as prediction markets gain significant traction among traders and institutions. Polymarket volumes have surged over the past year as regulatory pressure in the US has eased. Market participants increasingly use event contracts to express views on politics, economics, and corporate developments.
Strategy's Bitcoin treasury stood at 843,706 BTC as of the 1 Jun filing, according to the company's disclosures. While the financial value of the 32 BTC sale was relatively modest compared to that total, the outcome could help establish an important precedent for how prediction markets handle events confirmed only after a contract expires.
Strategy first adopted Bitcoin as a primary treasury reserve asset in 2020 and has since raised billions of dollars through debt and equity offerings specifically to acquire more BTC. Its strategy has made it a bellwether for corporate adoption of Bitcoin among listed companies. Polymarket, built on the Polygon , allows users to bet on real-world events using and has emerged as the leading platform in the decentralized prediction market sector.
