One of the most powerful techniques in the wheel strategy involves rolling cash-secured put positions to avoid assignment while continuously generating premium from the same collateral. This systematic approach allows option sellers to collect multiple credits from a single block of buying power, dramatically increasing the effective return on capital without deploying additional funds.
This tutorial demonstrates rolling multiple cash-secured put positions on KeyCorp (KEY), Walgreens Boots Alliance (WBA), Ford (F), and AT&T (T) using ThinkOrSwim. The core strategy involves monitoring extrinsic value across all positions, identifying puts trading near or below the $0.10 threshold, and rolling those positions to future expiration dates while targeting at least 1% return on investment for each roll transaction.
The key principle behind this strategy is capital efficiency: when you lack available buying power to open new positions, rolling existing puts allows you to continue generating income without assignment. Each roll extends the expiration date, collects additional premium, and maintains your optionality to eventually own shares at favorable prices when market conditions align with your strategic objectives.
The foundation of effective roll management starts with proper position monitoring. The demonstration shows creating a custom watchlist in ThinkOrSwim that displays extrinsic value for all cash-secured put positions in a single column, allowing rapid identification of positions approaching the roll threshold without opening each individual option chain.
Extrinsic value (also called time value) represents the portion of an option's price that exceeds its intrinsic value. For cash-secured puts, monitoring extrinsic value provides an early warning system for assignment risk:
The tutorial demonstrates adding a custom column to the ThinkOrSwim watchlist that displays extrinsic value for each position. This creates an at-a-glance dashboard showing which positions need attention. The watchlist includes positions on Ford, AT&T, KeyCorp, Walgreens, and VF Corporation, each showing real-time extrinsic values that fluctuate throughout the trading session.
Critical observation from the demonstration: extrinsic values can jump significantly in short timeframes. Walgreens showed extrinsic value bouncing between $0.05 and $0.15 every few seconds during volatile morning trading, illustrating why you need systematic monitoring rather than sporadic position checks.
The first roll demonstrated involves Ford (F), which presents a unique technical challenge: the strike price has been automatically adjusted by ThinkOrSwim due to a dividend payment, creating a non-standard strike of $12.32 instead of the original $12.50. This dividend adjustment affects how you approach rolling the position to future expiration dates.
ThinkOrSwim provides a "Create Rolling Order" function accessed by right-clicking on the position row in your position statement or active trader interface. The demonstration shows the following workflow:
The Ford position initially shows strike prices marked as "not traded" when attempting to roll one week forward. This occurs because the dividend-adjusted $12.32 strike price does not exist in future expiration cycles - only standard strikes like $12.00 and $12.50 are available. The solution involves pushing the expiration date further out until finding a timeframe with adequate liquidity and tradeable strikes.
The demonstration settles on rolling Ford approximately 31 days forward (from near-term expiration to March 28th), which provides a $0.14 credit. This represents more than 1% return on the $12.32 strike price, meeting the minimum profitability threshold for executing the roll.
| Position Detail | Original | After Roll |
|---|---|---|
| Strike Price | $12.32 (dividend adjusted) | $12.32 (maintained) |
| Expiration | Near-term (days remaining) | March 28th (+31 days) |
| Credit Received | — | $0.14 ($14 per contract) |
| ROI on Roll | — | 1.13% for 31 days |
When rolling positions with dividend-adjusted strike prices, you may need to push expiration dates further than your typical one-week increments to find tradeable strikes with adequate liquidity. Accept slightly longer timeframes when necessary to maintain the position and collect meaningful premium.
KeyCorp presents a more nuanced decision scenario: the extrinsic value hovers at $0.12, slightly above the typical $0.10 roll threshold but with only four days remaining until expiration. This creates a judgment call where you must balance the minimal time premium remaining against the transaction costs and effort of executing a roll.
The demonstration initially considers passing on rolling KeyCorp because the extrinsic value sits at $0.12, suggesting there is still some time premium to collect before assignment becomes likely. However, several factors push the decision toward rolling anyway:
The create rolling order interface initially suggests rolling KeyCorp one week forward for an $0.11 credit. However, this credit falls short of the 1% ROI target on the $14.00 strike (would need $0.14 minimum). The demonstration pushes the expiration date one additional week to March 15th (18 days out), which provides a $0.22 credit meeting the minimum profitability requirement.
| Roll Option | Days Extension | Credit | ROI | Decision |
|---|---|---|---|---|
| One Week | 7 days | $0.11 | 0.79% | Insufficient ROI |
| Two Weeks | 18 days | $0.22 | 1.57% | ✓ Executed |
The AT&T position demonstrates a challenging scenario where the stock trades significantly below the strike price and near-term roll options provide insufficient premium. This forces a decision between accepting assignment and owning shares versus rolling much further forward than typical to capture adequate income for maintaining the put position.
AT&T shows extrinsic value well below the $0.10 threshold at just $0.04, with 11 days remaining to expiration. The $17.00 strike sits $0.44 above the current trading price of $16.56, meaning the put is in the money and assignment is likely at expiration unless the stock rallies significantly.
The initial roll attempt shows meager credits for short-term extensions:
Frustrated by inadequate near-term premium, the demonstration extends the search to April 19th, approximately 53 days from the current date. This longer timeframe finally produces meaningful premium: $0.34 credit representing a 2% return on the $17.00 strike price, or approximately 1% per month over the extended holding period.
The decision to execute this unusually long roll stems from specific strategic considerations:
Rolling positions 6-8 weeks forward typically exceeds recommended timeframes for active put selling. However, this becomes acceptable when: (1) near-term rolls provide insufficient ROI, (2) you want to avoid assignment but lack capital for the bilateral wheel strategy, and (3) the extended timeframe produces a meaningful credit jump suggesting elevated IV from upcoming events.
After executing multiple roll transactions in ThinkOrSwim, accurate position tracking requires entering each roll into MyATMM's cost basis system. The demonstration shows the streamlined process for recording rolls, which ThinkOrSwim conveniently combines into single net transactions rather than forcing you to enter separate buy-to-close and sell-to-open legs.
When you roll a position in ThinkOrSwim, the platform executes two simultaneous transactions: buying to close your existing put and selling to open a new put at the extended expiration date. However, ThinkOrSwim reports this as a single net credit or debit transaction, dramatically simplifying the tracking requirements in MyATMM.
The demonstration shows tracking the Walgreens roll executed earlier in the day:
The demonstration emphasizes the importance of recording precise fees for each roll transaction. ThinkOrSwim charges fees for both the closing transaction and the opening transaction, even though they execute simultaneously as part of the roll order. For the Walgreens roll:
MyATMM automatically calculates the net premium received after commissions and fees when you enter these values in the temporary transaction section, ensuring your transaction history shows the actual cash impact of each roll rather than just the gross credit received.
After recording the Walgreens roll, MyATMM displays the cumulative position statistics showing $103 total premium collected on $2,250 collateral for this ticker. This running total demonstrates the power of the repeated rolling strategy: you have generated $103 in income from $2,250 in buying power without ever owning shares or deploying additional capital.
The demonstration repeats this process for each of the other rolled positions (Ford, AT&T, KeyCorp), building a complete transaction history that shows:
| Ticker | Latest Roll Credit | Total Premium Collected | Collateral |
|---|---|---|---|
| WBA | $24.68 | $103.00 | $2,250 |
| F (Ford) | $12.68 | $141.00 | $1,232 |
| T (AT&T) | $32.68 | $63.70 | $1,700 |
| KEY | $20.68 | $89.00 | $1,400 |
After entering all the day's roll transactions, the demonstration shows a critical best practice for option sellers: reconciling MyATMM's total cash balance against the actual brokerage account statement in ThinkOrSwim. This verification process catches entry errors, missed transactions, and ensures your tracking system remains perfectly synchronized with reality.
The MyATMM dashboard displays total account value calculated from all entered transactions, deposits, and withdrawals. After entering the four roll transactions, the demonstration navigates to the dashboard to verify this calculated total against the actual ThinkOrSwim account balance:
The mismatch prompts a review of the ThinkOrSwim account statement history, which reveals a rolled transaction on VF Corporation (VFC) executed on February 22nd that was never entered into MyATMM. This demonstrates why systematic reconciliation matters - without comparing totals regularly, tracking errors accumulate and cost basis calculations become increasingly inaccurate.
The missing VFC roll transaction details:
| Transaction Element | Value |
|---|---|
| Transaction Date | February 22nd |
| Transaction Type | Roll (combined buy-to-close and sell-to-open) |
| New Expiration | March 8th |
| Strike Price | $17.00 |
| Net Credit | $0.19 ($19 total) |
| Commissions & Fees | $1.32 total |
After entering this missed transaction following the same process used for the other rolls, the MyATMM dashboard balance updates to exactly match the ThinkOrSwim account balance of $12,784.00. This perfect alignment confirms that all transactions have been captured and the cost basis tracking system reflects true position values.
The demonstration concludes by highlighting recent MyATMM platform updates that streamline the workflow for managing multiple ticker positions. These enhancements address common user requests for faster navigation between positions and better tools for cleaning up completed or closed positions.
Previously, switching between ticker positions in the cost basis screen required clicking a dropdown menu, selecting the new ticker from a list, and waiting for the page to reload. The new interface adds previous and next arrows that allow sequential navigation through all your tracked tickers:
This navigation enhancement proves especially valuable when reviewing daily transactions across multiple positions, as you can quickly cycle through each ticker to verify entries without repeatedly accessing the dropdown menu.
The platform now includes a delete button for removing ticker symbols from your cost basis tracking system. This feature helps members clean up their position lists by removing tickers they no longer trade or positions they have completely closed out. Key aspects of the deletion system:
The demonstration shows the deletion interface but does not complete the operation, preserving the VFC position data. This safeguard approach (requiring typed confirmation) prevents accidental deletion of valuable transaction history that cannot be recovered after removal.
The systematic approach demonstrated across multiple positions provides a repeatable framework for managing cash-secured puts through rolling rather than assignment. This strategy maximizes capital efficiency by generating multiple income events from the same collateral while maintaining flexibility to eventually accept assignment when market conditions become favorable.
The decision framework for rolling versus accepting assignment depends on several strategic factors:
| Scenario | Recommended Action | Rationale |
|---|---|---|
| Limited buying power, no capital for covered calls | Roll the put | Owning shares without ability to write calls reduces income generation |
| Adequate buying power, strong bilateral opportunity | Accept assignment | Can immediately write covered call and new put for maximum income |
| Stock significantly below strike, poor roll credits | Consider assignment | Better to own shares and collect dividends than roll for minimal premium |
| Stock near strike, excellent roll credits available | Roll the put | Capture premium without capital commitment, maintain optionality |
| Elevated IV from upcoming earnings/dividends | Roll to capture inflated premium | Premium spike provides outsized credits for extended rolls |
The demonstration illustrates impressive capital efficiency from systematic rolling. Across the four positions rolled in this session, the collective results show:
While maintaining this exact pace daily is impossible due to time decay and market conditions, the numbers demonstrate how rolling cash-secured puts multiple times on the same collateral dramatically amplifies returns compared to simply selling puts and waiting for expiration.
Rolling cash-secured puts to avoid assignment does not eliminate the obligation to purchase shares if the stock remains below the strike price. Each roll extends your exposure to downside risk and commits collateral for longer periods. Stocks can decline significantly during extended timeframes, resulting in substantial losses when eventually assigned.
The 1% ROI target described in this tutorial represents a minimum threshold, not a guaranteed return. Market conditions, volatility changes, and individual stock dynamics can make achieving this target impossible for certain positions. Rolling for insufficient premium to avoid assignment may result in worse overall outcomes than accepting assignment and owning shares.
The positions and roll transactions shown in this tutorial are actual trades for educational demonstration purposes. Past performance does not guarantee future results. Option premiums, extrinsic value, and optimal roll timeframes vary significantly based on market conditions, implied volatility, and stock-specific factors.
This content is for educational purposes only and should not be considered financial advice. Rolling strategies require active monitoring, decision-making ability, and sufficient buying power to eventually accept assignment when rolling becomes uneconomical. Always consider your risk tolerance, capital availability, and investment objectives before implementing systematic rolling strategies.
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