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Days to Expiry
Option Selling Analyzer
Built for systematic options sellers

Systematic Options Selling, Precisely Tracked

See what is expiring, what is at risk, and what to do next — whether you are selling your first covered call or managing positions across multiple expiration cycles.

Track expirations before they become urgent
Review roll, hold, close, and assignment decisions in one place
Scan opportunities against your own DTE and risk rules

General information only. Not financial advice.

Days to Expiry dashboard showing expiring positions, DTE timeline, and next-action workflow

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Choose your path

One workflow. Two starting points.

Whether you are building your first options income system or refining one that already runs, Days to Expiry meets you where you are.

Building Your System

For investors learning covered calls, cash-secured puts, and the wheel. Start with calculators, backtests, primers, and guided examples.

  • Covered call & CSP calculators
  • Strategy backtesting
  • Step-by-step guides
Explore Beginner Tools

Optimizing Your System

For sellers already managing positions, expirations, rolls, and income goals. Sync your portfolio, set alerts, and review execution plans.

  • Portfolio sync & alerts
  • Expiration tracking
  • Roll & close guidance
See Pro Workflow
Reframe

Why options do not have to be gambling

The right comparison is not options versus no options — it is unpaid limit orders versus paid commitments. If you already have a buy price and a sell price, these strategies pay you while you wait.

You hold the shares or reserve the cash

Keeps the strategy grounded in assets you own or want to own — no leverage required.

You choose the price first

The strike is not random. It is your pre-decided buy or sell level.

The main risk is usually opportunity cost

On quality assets without margin, the common trade-off is capped upside, not account blow-ups.

Days to Expiry opportunity detail with premium, break-even, and assignment metrics

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Covered calls

Getting paid while you are willing to sell

Start with a stock you already own. Pick your sell price. Someone pays you today for the right to buy those shares before expiry.

  • You already own 100 shares of a stock or ETF you are comfortable holding.
  • You pick a sell price where you are happy to exit.
  • If price stays below the strike, you keep the shares and the premium.
  • If price runs through the strike, you sell at your chosen price and miss only the upside beyond it.

The key trade

You exchange some upside for immediate cash flow. That is opportunity cost, not hidden leverage.

Covered call search screen in Days to Expiry showing strike, premium, and risk metrics
Real covered call search view in Days to Expiry

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Cash-secured puts

Getting paid while you are willing to buy

Set aside the cash to buy shares at your dip price. Someone pays you today for the right to sell you the shares at that price.

  • You set aside enough cash to buy 100 shares if assigned.
  • You choose a buy-the-dip price where you genuinely want the shares.
  • If the stock stays above the strike, you keep the cash and the premium.
  • If the stock falls, you buy at your planned level with premium lowering your cost basis.

The key trade

You are not hoping for chaos. You are getting paid while waiting for an entry you already wanted.

Options scanner showing candidate contracts with probability and income context
Real scanner view for evaluating conservative put candidates

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The wheel

Get paid to enter, hold, and exit the same stock

Sell a cash-secured put on a quality ticker. If assigned, sell a covered call. If called away, you are back to cash and can restart. Both legs are just paid limit orders around the same asset.

1
Start with Cash

Have cash ready and a target stock in mind.

2
Sell Cash-Secured Put

Set your desired entry price and collect premium.

?
If worthless:

Keep premium, back to step 1

If assigned:

You own the stock, continue

3
Sell Covered Call

Set your target exit price and collect more premium.

?
If worthless:

Keep premium and shares, repeat step 3

If called away:

Stock sold, back to step 1

Wheel strategy backtest inside Days to Expiry
Backtest wheel cycles before committing real capital

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Wheel planning with strike and assignment context
Plan the CSP leg

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Strategy comparison screen
Compare wheel candidates

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LEAPS

A small convex allocation, funded by wheel income

The base engine is boring on purpose. A smaller slice of collected premium can fund long-dated calls on high-conviction themes. Defined risk, allocated from income rather than capital.

A simple allocation story

Keep most of the portfolio in wheel-friendly assets, then allocate only 10%–30% of collected premium to a small LEAPS allocation. If the thesis fails, the loss is limited to that budget.

LEAPS comparison screen showing different long-dated call opportunities
Compare long-dated upside ideas

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LEAPS backtest showing how different allocations changed outcomes
Test how a small LEAPS allocation changes historical outcomes

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Interactive calculator

See how wheel income funds your LEAPS

Adjust your monthly wheel income and allocation % to see the barbell in action.

Monthly wheel income$500

Conservative estimate based on 1-2% monthly yield on cash-secured positions.

LEAPS allocation (% of income)20%
Conservative (5%)Aggressive (40%)
$500
Monthly wheel income
$100
To LEAPS (20%)
$400
Reinvested/cash (80%)

The convexity: limited risk, exponential upside

Stock -50%
-$2,800
Max loss
Stock +30%
$0
Breakeven
Stock +100%
+$8,400
3x
Stock +200%
+$22,400
8x
Stock +300%
+$56,000
20x+
Annual LEAPS budget:$1,200

One +300% winner returns $56,000— that's a 47x your entire annual LEAPS budget from a single position.

Visual breakdown$500 total
80% Reinvest
20% LEAPS
Base (reinvest/cash)
Convex (LEAPS upside)

Why this is convexity, not speculation

Each LEAPS is only 233% of your annual budget. One +300% winner returns $56,000 — enough to fund your LEAPS program for 47years. The wheel base keeps generating income regardless. That's the barbell: boring base + lopsided upside.

Guardrails

Making this work long-term

These aren't rules to memorise. They are the defaults that keep a premium-selling strategy from turning into something it shouldn't be.

Own quality assets only

Only sell covered calls on tickers you are comfortable owning long-term. Positions should survive assignment without regret.

Treat upside caps as opportunity cost

Covered calls limit your upside. Know your strike before you sell. Backtesting confirms the expected trade-off on each ticker.

Keep LEAPS small and funded

Size the convex allocation from collected premium—not from underlying capital. A defined-risk loss hurts less than a capital loss.

Option finder showing assignment probability and ROI for covered call candidates
Assignment probability and ROI at a glance

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Why the tool helps

All the numbers you need, in one view

  • Assignment odds in plain language

  • ROI and DTE side-by-side

  • Backtests before trades

  • One place to track premium income

Is this for me?

Know before you start

Systematic options selling works best for investors who treat expiration management as a repeatable process, not a one-off trade.

This is for you if…

  • You sell options for income and need clarity on what is expiring soon
  • You want a repeatable weekly review instead of ad-hoc spreadsheet checks
  • You are willing to learn a small amount of options vocabulary
  • You think in terms of expiration cycles, not just quarterly performance

Skip this if…

  • You want to bet on short-term price moves without a plan
  • You are not comfortable holding a stock long-term if assigned
  • You cannot stomach weeks of unrealised losses occasionally
  • You need capital to be fully liquid at any moment

The workflow

  • Review open positions by expiration and DTE risk
  • Decide whether to hold, close, roll, or let assignment happen
  • Scan new opportunities against your capital and risk rules
  • Track premium capture and income across every cycle

Want to see the full platform? Explore the demo portfolio

Income estimator

What could your portfolio yield?

Enter your portfolio size and model a rough premium income estimate before you trade a single option.

$
60%

Most investors start at 50%–70% and adjust from there.

Strategy posture

See what is new in action

A quick walkthrough of the latest portfolio and strategy features

Frequently asked questions

Turn scattered expiration decisions into a weekly system

Review what is expiring, decide whether to hold, close, roll, or let assignment happen, then scan for the next opportunity.

General information only. Not financial advice.