MicroStrategy maps converts equitization over 3-6 years

Saylor plans to equitize Strategy’s convertible bonds within 3–6 years

michael saylor plans to convert Strategy’s outstanding convertible bonds into equity within roughly three to six years. The stated aim is to reduce debt and simplify the capital structure.

In practice, equitizing convertibles generally depends on the stock trading at or above each bond’s conversion price. When shares are below those thresholds, bondholders typically retain the bonds until maturity rather than convert.

Why it matters: dilution, liquidity, and capital-structure simplification

Equitizing debt can streamline financing and lower future refinancing risk, but it shifts obligations into common equity and raises potential dilution if conversion becomes attractive. Saylor has framed the goal as structural simplification and balance-sheet durability.

“equitize that as the options arrive … and simplify our capital structure,” said Michael Saylor, as reported by Financial Times.

As reported by Forbes, the plan’s feasibility hinges on the shares trading at a premium to market NAV, with convertibles issued far out of the money, often 35%–55% above the stock, and carrying low or zero cash coupons. If conditions strengthen, those features keep financing costs low but increase dilution risk if the stock moves in the money.

Reliance on perpetual preferred stock as replacement capital introduces fixed dividend costs and market-access risk, as reported by Fortune. If market appetite fades or valuations weaken, those dividends persist even as flexibility narrows.

When a convertible’s conversion price is above the current stock price, holders have little incentive to exchange debt for equity. Near term, that dynamic reduces the likelihood of organic conversion and keeps maturities and refinancing needs in focus.

As reported by Barron’s, S&P Global has highlighted liquidity risk because many convertibles are out of the money. Without a sustained share-price move above conversion levels, cash repayment or restructuring pressure could rise as maturities approach.

Execution within three to six years therefore remains conditional on market support, sufficient equity valuation, and investor demand for replacement capital. None of those conditions are guaranteed through the cycle.

Scenarios, risks, and conditions for equitizing debt

OTM vs ITM mechanics: conversion price, incentives, and dilution

Out-of-the-money convertibles do not convert because equity value at conversion is inferior to holding the bond. In-the-money convertibles can convert, reducing debt but diluting existing shareholders. Dilution scales with principal, conversion ratio, and share price.

Conversion timing also matters. A late-cycle move into the money may bunch conversions and elevate dilution near maturities, while a gradual rise allows staged equitization and operational planning.

Liquidity risk, preferred stock costs, and Bitcoin sensitivity

If convertibles remain out of the money into maturity, issuers face cash repayment or refinancing needs. That elevates liquidity risk, especially if capital markets tighten or spreads widen at the wrong time.

Preferred stock can substitute for convertibles but adds fixed dividends and potential call constraints. The structure may stabilize maturities while increasing ongoing financing costs and sensitivity to market access.

At the time of this writing, Bitcoin is about $68,928 with very high 12.37% volatility and neutral momentum by RSI. Such swings can affect Strategy’s refinancing windows and investor appetite for equity-linked capital.

FAQ about convertible bonds

Which Strategy convertible tranches mature between 2027–2030 and what are their conversion prices versus the current share price?

Tranches are due between 2027 and 2030. Conversion prices are described as above the current share price, implying out-of-the-money status. Exact tranche-by-tranche terms were not provided here.

How likely is bondholder conversion vs. cash repayment if the stock stays below the conversion price?

Below the conversion price, bondholders generally avoid conversion. Cash repayment at maturity or refinancing by the issuer becomes more likely while shares remain out of the money.