A Look At MicroStrategy (MSTR) Valuation As Bitcoin Buying Pauses For Convertible Note Buybacks

May 26, 2026

Strategy (MSTR) has paused its steady Bitcoin buying to repurchase about US$1.5b of 2029 convertible notes at a discount, shifting attention to debt reduction, capital recycling, and balance sheet resilience.

See our latest analysis for Strategy.

The recent pause in Bitcoin purchases and focus on repurchasing 2029 convertible notes comes after a weak near term share price patch, with the 1 day, 7 day and 30 day share price returns all down. This contrasts with the 90 day share price return of 28.31%, a 1 year total shareholder return decline of 56.73%, and a very large 3 year total shareholder return, suggesting momentum has cooled recently after a powerful multi year run.

If you are weighing what this balance sheet reset means for crypto linked equities more broadly, it could be a good moment to scan other Bitcoin and blockchain related plays using our 22 cryptocurrency and blockchain stocks

With Strategy’s share price down over the past year, yet still carrying a very large 3 year total return and only a small intrinsic discount to estimated value, are you looking at a reset entry point or a stock that already reflects future growth?

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Most Popular Narrative: 75.9% Undervalued

With Strategy’s last close at $159.89 and the most followed narrative pointing to a fair value of $663, the gap between price and thesis is wide and very explicit.

Valuing MicroStrategy remains the ultimate $1,000,000 question. It represents a completely unique investment concept, directly tied to the performance of a highly volatile digital commodity: Bitcoin. As a leveraged beta play on Bitcoin, MicroStrategy introduces not only the inherent risks of Bitcoin’s volatility but also the amplified exposure from its aggressive financial strategies.

Read the complete narrative.

Want to see what underpins that big valuation spread? The narrative leans on aggressive treasury expansion, ambitious Bitcoin holding targets, and margin assumptions more often reserved for high growth compounding stories.

Result: Fair Value of $663 (UNDERVALUED)

Have a read of the narrative in full and understand what’s behind the forecasts.

However, this hinges on Bitcoin sentiment and leverage staying supportive, and a sharp pullback or tighter funding markets could quickly compress that 75.9% undervaluation gap.

Find out about the key risks to this Strategy narrative.

Next Steps

With sentiment split between concern over risks and optimism about rewards, this is a moment to move quickly and test the thesis against the data yourself using our 2 key rewards and 1 important warning sign

Looking for more investment ideas?

If you stop at a single stock, you risk missing other opportunities that better fit your goals, risk tolerance, and preferred mix of quality and value.

This article by Simply Wall St is general in nature. We provide commentary based on historical data
and analyst forecasts only using an unbiased methodology and our articles are not intended to be financial advice.
It does not constitute a recommendation to buy or sell any stock, and does not take account of your objectives, or your
financial situation. We aim to bring you long-term focused analysis driven by fundamental data.
Note that our analysis may not factor in the latest price-sensitive company announcements or qualitative material.
Simply Wall St has no position in any stocks mentioned.

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