Strategy is pushing for a shareholder vote on a proposal to change the dividend payment cycle for its STRC preferred shares to twice a month from once a month, and Peter Schiff has criticised the move.

On May 27, blockchain media outlet BeInCrypto reported that the voting deadline is June 8, and that if the proposal passes, the first record date is set for June 30.

The key point of the proposal is to increase dividend frequency while keeping the annualized yield at 11.5 percent. Strategy said that increasing the number of payments can reduce delays in reinvestment and improve market efficiency, and can support price stability around STRC's $100 par value. Chairman Michael Saylor (마이클 세일러) urged shareholders on social media to vote, saying, "Please participate in the vote to further develop STRC."

For the proposal to take effect, it needs approval from both MSTR and STRC holders. Saylor stressed that the change offers tangible benefits for retail investors. Strategy said about 80 percent of STRC is held by retail investors, and argued that changing the dividend cycle would directly affect cash flow management for the majority of holders. STRC's dividend rate has been maintained at 11.5 percent since April, and the vote is separate from the board's calculation of the dividend rate.

Debate in the market over Strategy's funding structure is also resurfacing alongside the vote. Schiff, known as a gold advocate, criticised the company for selling STRC to raise cash, using those funds to buy Bitcoin (BTC), and then relying on new issuance again to pay dividends. He took aim at Saylor, saying, "They are running out of cash. What will you sell next to keep the wheels from coming off?"

The back-and-forth is drawing more attention as it intersects with Strategy's recent financial measures. Strategy used $1.38 billion in cash-equivalent assets to buy back $1.5 billion of convertible bonds due in 2029 at an 8 percent discount. After the deal, dollar reserves fell to about $871 million from about $2.0 billion.

In its first-quarter 2026 earnings release, Saylor acknowledged that the company could sell Bitcoin to secure funding for dividends if other capital-raising options are lacking. Schiff said the remarks confirmed his concerns. He took issue with the point that because Bitcoin does not generate cash flow, sustaining dividends would require external financing or asset sales.

Still, Strategy bought an additional 24,869 BTC over the same period using proceeds from issuing STRC and common shares. Total holdings increased to 843,738 BTC. The company paused additional Bitcoin purchases for one week while the convertible bond buyback was being completed, but it did not abandon its existing Bitcoin accumulation strategy.

In this situation, STRC shareholders' decision on June 8 is expected to be a gauge of how much income-oriented investors trust the current dividend model. A key point to watch is whether expanding dividend frequency will be received positively by retail investors, or whether liquidity concerns will influence the vote.

$MSTR did not really buy back convertible bonds at a bargain. Strategy prepaid a zero-interest loan two years early at roughly present value. The so-called 8% discount reflects the time value of money. @Saylor reduced debt, but gave up free financing and burned badly needed cash.