"Working Better": Saylor Teases BTC Buy After Strategy Sells For First Time Since 2022

Bitcoin is extending its recent weakness overnight (hurt by US-Iran tensions escalating again), trading back below its 100DMA after Strategy (MSTR) sold 32 bitcoin between May 26 and May 31 at an average net price of $77,135 a coin, totaling $2.5 million (disclosed in an 8-K filing on Monday).

Proceeds from the bitcoin sales are expected to be used to fund distributions on preferred stock, the firm said.

This is the first time Strategy has sold bitcoin since December 2022, when the company offloaded 704 BTC, according to onchain analyst Ai Yi.

However, the firm reportedly bought 810 BTC just two days after the sale at a lower price in a tax loss trade.

Strategy now holds a total of 843,706 BTC following the reduction - worth around $61 billion - bought at an average price of $75,699 per bitcoin for a total cost of around $63.9 billion, including fees and expenses.

In addition, for the week, Strategy raised $128.3 million through its at-the-market (ATM) common stock program and allocated a small portion of the proceeds to increase its U.S. dollar cash reserve from $871 million to $900 million.

Anticipated?

The Block.co reports that Strategy's bitcoin sale was anticipated.

Its executives previously said during its first-quarter 2026 earnings call that it may sell some of its holdings to fund dividends for STRC, Strategy's perpetual preferred stock designed to maintain a $100 par value and offer high yields to investors.

Saylor explained then that the sale would eventually help Strategy buy more bitcoin than it would sell to cover STRC's dividends.

He also noted that the firm's current position requires bitcoin to appreciate at 2.3% annually for its existing holdings to cover STRC dividend obligations indefinitely, without selling any common stock.

Today's sale announcement comes shortly after onchain data from Arkham Intelligence showed that Strategy moved roughly 411.6 BTC from its custody account on Coinbase Prime to a cold wallet address on the platform on May 28.

This prompted the odds of Strategy selling bitcoin before the end of 2026 to surge to 84%.

Strategy also noted it has purchased 2.6 times the amount of bitcoin mined in 2026 so far, describing MSTR as a "BitVac."

"Working Better"

But, as CoinTelegraph.com reports, before the 8-K filing was released (but after the actual sales), Strategy chairman Michael Saylor on Sunday signaled the Bitcoin treasury company would be announcing fresh purchases of the cryptocurrency in the coming days.

The social media post comes just days ahead of a proxy vote that depends in large part on retailer shareholders to enable semi-monthly dividend payouts on the company’s STRC perpetual preferred stock.

“Working Better” was Saylor's tweet late Sunday morning to accompany a bubble chart tracking Strategy’s Bitcoin (BTC) purchases over the past nearly six years.

“Working Better” tweet. Source: Michael Saylor

That chart, from Iceland-registered StrategyTracker.com, has been consistently posted by Saylor in the days ahead of news of a purchase by the biggest publicly traded Bitcoin holder.

To be sure, any purchases to be announced will likely reflect the company bought at or below the average cost of previous BTC purchases.

Retail investors pressed to vote on STRC dividend change

Strategy is proposing to pay semi-monthly dividends on STRC, instead of monthly. The company claims that if approved and adopted, it will lead to reduced reinvestment lag, enhanced liquidity, market efficiency and increased price stability.

Just days ahead of the June 7 proxy vote deadline, Saylor and Strategy are pressing retail shareholders to return their proxy votes. On an internal company channel, Strategy’s investor relations team posted a message to all employees concerning the company’s 2026 annual meeting and provided links to the proposals under consideration by shareholders.

Part of message to Strategy employees from internal website. Source: Company filing on Edgar

“The amendment for STRC to pay semi-monthly dividends, needs 50% of all 85M shares outstanding as of April 17, 2026, to pass, which means every single vote counts,” read a May 28 post on Strategy’s verified feed on X.com.

CEO Phong Le posted a video a day earlier thanking STRC shareholders for their trust.

“I wanted to personally walk you through the proposed amendment and what it means for you,” he said as an introduction to the minute-and-a-half video.

Retail investors have shown limited interest in casting proxy votes. A November research note from The Harvard Law School Forum on Corporate Governance revealed data that showed retail investors have consistently voted only about 29% of their owned shares during the past five proxy voting seasons. Institutional holders have voted about 77%.

A Cyclical Bottom?

Bloomberg's Andre de Silva writes that while a steep record daily capital drain in US Bitcoin ETFs exposes immediate fatigue, past precedent suggests that such severe capitulation frequently cleanses short-term positioning and signals a cyclical bottom for the digital asset.

AI infrastructure and semiconductor equities have attracted the most attention, but because Bitcoin typically retains its status as a high-beta proxy for broader risk appetite during macro expansions, this temporary diversion of capital suggests that a classic catch-up rally remains on the table.

The initial euphoria surrounding US Bitcoin ETFs has cooled, giving way to an unprecedented streak of redemptions. Investors pulled $2.96 billion from the funds over 10 consecutive trading sessions to close out May, according ETF providers. That culminated in $2.4 billion in total net outflows for the month. This sharp reversal stands in contrast to the preceding two months of healthy institutional demand, which saw combined inflows of over $3.3 billion across March and April. The late-May selling pressure spared no one, with BlackRock’s usually resilient IBIT hit by a near-record single-day redemption following a massive off-exchange block trade.

This capital flight highlights a stark divergence recently between digital and traditional risk assets.

While global stock benchmarks like the S&P 500, Nasdaq, and Asia’s top indices such as the Kospi scale new heights, Bitcoin has decoupled from the broader market rally.

Even the prospects of supportive regulation have failed to arrest the slide. This includes the Senate Banking Committee recently advancing the landmark Clarity Act to establish a formal crypto market framework, an initiative that Polymarket prices with a 55% chance of being officially signed into law this year. Instead, capital is aggressively migrating toward memory chip and semiconductor companies and, as indicted by David Savage, including Asia, leaving Bitcoin looking sluggish by comparison.

Beneath the surface, this purge of the ETF channel acts as a reliable contrarian indicator.

Historically, when US Bitcoin ETF flows hit these types of extreme negative troughs, they frequently coincided with local market bottoms.

Similar washouts during early 2025 preceded sharp, multi-month recoveries once institutional selling hit exhaustion.

While crypto sentiment has dropped into ‘Fear’ territory according to the Alternative.me Crypto Fear and Greed Index, which is a multi-factor market sentiment tracker, this cleansing of overleveraged or short-term positions might be exactly what the digital asset needs to reset and build a sustainable floor.