Ask ten wheel traders when they roll their puts and you'll get ten different answers. "When I feel nervous." "When the stock drops through my strike." "When my broker tells me to." None of these are wrong, exactly — but none of them are optimal either. The best roll decisions are mathematical, not emotional.
Here are the four specific signals that tell you — with numbers, not feelings — whether rolling is the right move.
What Is the 21-DTE Rule for Rolling CSPs?
Research from tastytrade shows that theta decay accelerates dramatically inside the final 21 days before expiration. If your CSP has already captured more than 50% of its maximum profit potential and you still have 21 or more days until expiration, holding and waiting isn't efficient. The remaining premium isn't enough to justify the ongoing capital commitment and gamma risk.
If Current Premium ≤ 50% of Original AND DTE ≤ 21 → Close or RollRolling lets you lock in the existing gain and immediately start collecting premium on a new position with better time value. Holding to expiration for the last 50% of premium takes twice as long as collecting the first 50%.
Should You Ever Roll for a Net Debit?
Rarely, and only with very clear justification. As a general rule, a roll that doesn't produce a net credit is not a roll worth making. If you can't find a strike or expiration that gives you a positive net credit after closing costs, that's often the market telling you that accepting assignment and moving to covered calls is the better path forward.
Net Roll Credit = New STO Premium − Old BTC Cost > $0If you're deep in the money and the only rolls available are net debits, you're likely better off taking assignment and beginning your covered call phase immediately.
What Delta Should You Target When Rolling?
When your CSP's delta pushes above 0.40-0.50, the market is pricing in a high probability of assignment. At this point, a roll down in strike (moving to a lower strike price) can bring delta back to a more comfortable 0.20-0.30 range. The target delta tells you two things: roughly how much premium you'll collect and roughly how much downside buffer you're building in.
How Do You Calculate Whether a Roll Actually Improves Your Position?
After any proposed roll, recalculate your break-even with the roll credit included:
New Break-Even = New Strike − (Accumulated Premiums + Roll Credit) ÷ 100If the new break-even is lower than your current break-even, the roll is mechanically improving your position. If it isn't — if all you're doing is buying time without reducing your real risk — it's worth asking whether you're rolling toward a better position or just delaying an inevitable assignment.
A Four-Step Decision Framework
- Is the stock still a company you'd want to own long-term? If the fundamental thesis has changed, rolling doesn't help. Close the position.
- Can you roll for a meaningful net credit? If not, take assignment and start selling covered calls.
- Does the roll lower your break-even? If yes, it's mechanically improving your position. Roll.
- How many times have you already rolled this position? Multiple rolls on the same position usually signal that you should reassess the thesis, not roll again.
Use OptionWheelTracker to log every roll and see your cumulative net credits across an entire campaign. Over time, seeing your running ACB drop with each roll makes the math — and the discipline — much easier to maintain.