Strategy (MSTR) Stock: Saylor Drops His Favorite Signal — Is a Bitcoin Buy Coming?

TLDR

• Michael Saylor posted his signature “Working Better” chart on Sunday, widely seen as a signal that Strategy is about to announce a new Bitcoin purchase.
• Strategy paused buying after repurchasing $1.5 billion in convertible notes due 2029, paying roughly $1.38 billion in cash.
• The firm holds 843,738 BTC at an average cost of $75,701, while Bitcoin was trading around $73,566 — below that average.
• Strategy moved 411.48 BTC to Coinbase Prime on May 29, then withdrew a near-identical amount the next day — analysts say it may be a tax-loss harvesting move.
• A June 7 proxy vote on semi-monthly STRC dividends is approaching, and Strategy is pushing retail shareholders to participate.

Bitcoin was trading around $73,566 at the time of writing — about 3.65% lower on the month — sitting below Strategy’s average purchase price of $75,701 per coin.

Strategy Inc, MSTR

That hasn’t stopped Michael Saylor from signaling another buy.

On Sunday, May 31, the Strategy executive chairman posted his now-famous “Orange Dots” bubble chart to X, captioned simply “Working Better.” That chart has reliably preceded purchase announcements over the past several years. The market took notice.

Strategy last bought 24,869 BTC worth over $2 billion, funded through a $2 billion offering of its Variable Rate Series A Perpetual Stretch Preferred Stock and $84 million raised via MSTR Class A common stock.

As of May 25, Strategy holds 843,738 BTC valued at approximately $62.24 billion, with cash holdings of around $871 million.

Why Strategy Paused Buying

The company’s recent pause had a specific reason. Strategy bought back the entire $1.5 billion principal of its 0% Convertible Senior Notes due 2029, paying around $1.38 billion in cash — settling the debt at a discount.

The buyback was an unusual detour for a firm that typically channels capital into Bitcoin without hesitation. But it cut the company’s convertible debt load and freed up balance sheet flexibility going forward.

The Coinbase Prime Transfer

On May 29, on-chain tracking platform Lookonchain flagged that Strategy moved 411.48 BTC — roughly $30.3 million — to Coinbase Prime across two transactions following a small test transfer.

Some read this as a potential selloff. But the very next day, Strategy withdrew approximately the same amount — 411.5 BTC worth around $30.2 million — back from Coinbase Prime.

Crypto Banter CEO Ran Neuner offered an explanation: the move was likely a tax-loss harvesting tactic. The strategy involves selling Bitcoin at a loss and immediately repurchasing it to record that loss on paper.

Blockstream CEO Adam Back pointed out on Sunday that Bitcoin’s 200-week moving average has risen well past $61,000 — a level some technical traders watch as a long-term trend signal.

Strategy is also pressing retail shareholders ahead of a June 7 proxy vote. The vote concerns a proposal to shift STRC perpetual preferred stock dividends from monthly to semi-monthly payments. The company says this would reduce reinvestment lag and improve liquidity.

The amendment needs 50% of all 85 million shares outstanding to pass. Historically, retail investors vote only about 29% of their owned shares, compared to 77% for institutional holders.

CEO Phong Le posted a video on May 30 asking STRC shareholders to cast their votes before the deadline.

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