Public recipe: cash-secured wheel sized to equity, 35 DTE / 2% OTM puts and calls, manage at 21 DTE. Simulated window 2024-10-18 to 2026-10-16.
Two paired wheel simulations on MSFT, one managed at 21 DTE. On this simulation the 21-Day Rule finished -8.6 pp behind holding to expiry — managing early hurt here.
| Metric | Standard (hold to expiry) | 21-Day Rule | Delta |
|---|---|---|---|
| Total return | 12.0% | 3.4% | -8.6 pp |
| Annualized return | 5.9% | 1.7% | -4.2 pp |
| Buy-and-hold return | 26.5% | 26.5% | 0.0 pp |
| Max drawdown (from peak equity) | 24.7% | 19.5% | -5.1 pp |
| Assignment rate | 33.3% | 23.1% | -10.2 pp |
| Call-away rate | 37.5% | 27.3% | -10.2 pp |
| Average cycle return | 1.3% | 0.1% | — |
| Sample cycles | 9 | 26 | — |
| History days | 728 | 728 | — |
| Entry fills | 17 | 48 | — |
| Entry fills priced from real option bars | 47% | 50% | — |
| 21-DTE buy-backs priced from real option bars | — | 52% | — |
Across the 37 published tickers, the 21-Day Rule finished ahead of holding to expiry on 18 and behind on 19. The MSFT total-return delta of -8.6 pp ranks 27th of 37 (1st is where managing early helped most); the median delta is -1.4 pp.
Without the rule, the standard arm returned 12.0% against 26.5% for buy-and-hold, so the plain wheel trailed holding the shares by 14.5 percentage points in this simulation.
Among its mega-cap tech and semiconductor peers AMZN, GOOGL, META and NVDA, the rule finished ahead of holding to expiry on 2 of 4; MSFT itself came in at -8.6 pp.
The separate 10 DTE / 2% OTM wheel snapshot for MSFT shows a put assignment rate of 30.3% and wheel P&L of $4,976 against $11,089 for buy-and-hold. That is a different recipe from the 35 DTE study on this page, so the two results are not additive.
| Metric | MSFT | Family median | Rank (highest first unless noted) |
|---|---|---|---|
| Rule total-return delta | -8.6 pp | -1.4 pp | 27th of 37 |
| Rule drawdown delta | -5.1 pp | -1.3 pp | 9th of 37 (lowest first) |
| 21-Day total return | 3.4% | 14.4% | 30th of 37 |
| 21-Day annualized return | 1.7% | 7.0% | 30th of 37 |
| Standard total return | 12.0% | 14.7% | 23rd of 37 |
| 21-Day max drawdown | 19.5% | 20.8% | 15th of 37 (lowest first) |
| 21-Day call-away rate | 27.3% | 39.1% | 32nd of 37 |
| Standard annualized return | 5.9% | 7.1% | 23rd of 37 |
| Buy-and-hold return | 26.5% | 38.6% | 24th of 37 |
| Standard max drawdown | 24.7% | 24.3% | 20th of 37 (lowest first) |
| Standard assignment rate | 33.3% | 30.8% | 15th of 37 |
| 21-Day assignment rate | 23.1% | 32.0% | 27th of 37 |
| 21-Day sample cycles | 26 | 27 | 20th of 37 |
| 21-Day average cycle return | 0.1% | 0.5% | 33rd of 37 |
| Ticker | Standard return | 21-Day return | Rule delta | Buy-and-hold | Standard drawdown | 21-Day drawdown | Standard assignment | 21-Day assignment |
|---|---|---|---|---|---|---|---|---|
| MSFT | 12.0% | 3.4% | -8.6 pp | 26.5% | 24.7% | 19.5% | 33.3% | 23.1% |
| AMZN | 3.0% | 8.8% | +5.8 pp | 32.3% | 24.1% | 20.6% | 41.7% | 36.4% |
| GOOGL | 21.0% | 35.2% | +14.3 pp | 108.4% | 24.7% | 21.6% | 21.4% | 23.3% |
| META | 34.4% | 21.7% | -12.7 pp | 23.0% | 30.8% | 20.8% | 60.0% | 41.7% |
| NVDA | 60.9% | 22.1% | -38.8 pp | 55.2% | 28.2% | 27.6% | 25.0% | 46.2% |
MSFT wheel snapshot — the other published study on this ticker.
Month-end P&L of holding 100 MSFT shares over the same window as this study, taken from the stored series of the 10 DTE wheel snapshot. The best month for holders was 2026-07 ($9,170) and the worst was 2026-06 (−$7,722).
| Month | Buy-and-hold P&L | Change in month | Running high | Below its peak | Worst fall so far |
|---|---|---|---|---|---|
| 2024-10 | −$1,181 | — | $1,437 | $2,618 | $2,618 |
| 2024-11 | $530 | $1,711 | $1,437 | $907 | $2,618 |
| 2024-12 | $334 | −$196 | $3,630 | $3,296 | $3,296 |
| 2025-01 | −$310 | −$644 | $3,630 | $3,940 | $3,947 |
| 2025-02 | −$2,117 | −$1,807 | $3,630 | $5,747 | $6,193 |
| 2025-03 | −$4,277 | −$2,160 | $3,630 | $7,907 | $7,907 |
| 2025-04 | −$2,290 | $1,987 | $3,630 | $5,920 | $9,990 |
| 2025-05 | $4,220 | $6,510 | $4,253 | $33 | $9,990 |
| 2025-06 | $7,925 | $3,705 | $7,929 | $4 | $9,990 |
| 2025-07 | $11,534 | $3,609 | $11,534 | $0 | $9,990 |
| 2025-08 | $8,853 | −$2,681 | $11,748 | $2,895 | $9,990 |
| 2025-09 | $9,979 | $1,126 | $11,748 | $1,769 | $9,990 |
| 2025-10 | $9,965 | −$14 | $12,391 | $2,426 | $9,990 |
| 2025-11 | $7,385 | −$2,580 | $12,391 | $5,006 | $9,990 |
| 2025-12 | $6,546 | −$839 | $12,391 | $5,845 | $9,990 |
| 2026-01 | $1,213 | −$5,333 | $12,391 | $11,178 | $11,178 |
| 2026-02 | −$2,542 | −$3,755 | $12,391 | $14,933 | $15,760 |
| 2026-03 | −$4,799 | −$2,257 | $12,391 | $17,190 | $18,530 |
| 2026-04 | −$1,038 | $3,761 | $12,391 | $13,429 | $18,530 |
| 2026-05 | $3,208 | $4,246 | $12,391 | $9,183 | $18,530 |
| 2026-06 | −$4,514 | −$7,722 | $12,391 | $16,905 | $18,924 |
| 2026-07 | $4,656 | $9,170 | $12,391 | $7,735 | $18,924 |
| 2026-08 | $8,913 | $4,257 | $12,391 | $3,478 | $18,924 |
| 2026-09 | $9,474 | $561 | $12,391 | $2,917 | $18,924 |
| 2026-10 | $11,089 | $1,615 | $12,529 | $1,440 | $18,924 |
One ticker and one window prove nothing general; the rule arm sometimes cannot exit at 21 DTE
Period 2024-10-18 to 2026-10-16, refreshed 2026-10-18.
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