Cash-secured put assignments mark the transition point where cash collateral becomes stock shares, triggering a workflow shift from monitoring put obligations to implementing covered call strategies. This demonstration walks through the complete assignment handling process on BITO (ProShares Bitcoin Strategy ETF), showing how a $32 strike cash-secured put that collected $186 premium ultimately got assigned when BITO dropped to $29, and how that assignment immediately enabled bilateral position management selling both covered calls and additional cash-secured puts for continued premium collection.
The workflow begins with reviewing brokerage account statements to identify assignment events, then transitions to systematic transaction recording in MyATMM that tracks the stock purchase, updates cost basis calculations, and reconciles account balances. Once the assignment is recorded and shares are owned, the strategy pivots to selling covered calls against those shares while simultaneously placing another cash-secured put at the new lower price point, creating the bilateral structure that generates premium regardless of directional movement.
What makes this approach particularly powerful for wheel strategy implementation is how assignments become opportunities rather than problems. When that cash-secured put gets assigned and forces stock purchase at $32 per share, you're not stuck holding an underwater position. Instead, you own shares that can generate covered call income immediately, and you can sell another cash-secured put at an even lower strike price, positioning for additional share accumulation through dollar cost averaging if BITO continues declining.
The assignment discovery process starts by reviewing your broker account to see the results of options that expired during the previous week and determine which positions expired worthless versus which generated assignment obligations.
The first indication of assignment typically appears in your broker's position monitoring tab. In this case, checking the monitor tab in the IRA account showed BITO shares appearing in the position list, signaling that a put option had been exercised and shares were assigned to the account.
This immediate visual confirmation in the monitoring tab provides the first clue before diving into detailed account statements. When you see shares appear for a ticker where you had cash-secured puts but no previous stock ownership, you can safely assume assignment occurred on one or more of those put contracts.
To get precise assignment details including execution date, assignment price, and commission structure, you need to review the detailed account statement transaction history. This shows the complete chronological record of every trade, assignment, and account activity.
The statement review process works backward from the current date to find the relevant transactions:
The April 1st fill at $1.86 per share on one contract generated $186 in gross premium before commissions. This exceeded the $180 target by $6, demonstrating how limit orders protect against bad fills while still capturing favorable price improvements when market conditions shift in your favor overnight.
Before recording the assignment transaction, checking the current BITO price provides context for the assignment decision. The chart review showed BITO had been experiencing choppy price action, bouncing up and down within a range. The last traded price sat at $29, well below the $32 strike price where the cash-secured put was sold.
This $3 per share distance between the $32 strike and $29 current price meant the put finished deep in the money at expiration, virtually guaranteeing assignment. The put buyer exercised their right to sell shares at $32 when they could only get $29 in the open market, transferring those shares to you at the $32 strike price as the put seller.
Understanding this price relationship clarifies why assignment occurred and what it means for your position: you now own shares with a $32 per share cost basis while the market trades at $29, creating an immediate unrealized loss of $3 per share that will be offset by the $1.86 per share in premium already collected plus any future premium from covered calls and additional cash-secured puts.
After identifying the assignment in your brokerage statements, the systematic workflow continues by recording all relevant transactions in MyATMM to maintain complete position history and accurate cost basis calculations.
Before making any transaction entries, the demonstration shows checking that the MyATMM dashboard balance ($10,125.25) matches the ThinkOrSwim brokerage balance exactly. This pre-entry balance check confirms that all previous transactions were recorded accurately and provides a clean baseline before adding new data.
This verification step prevents compounding errors. If the balances don't match before you start entering new transactions, you know there's an existing data problem that needs correction before proceeding. Waiting until after you enter new transactions makes it much harder to identify where the discrepancy originated.
Since this represents the first BITO position in this account, the initial step requires adding BITO as a new ticker symbol to the cost basis tracking dropdown. This is accomplished by:
Once added, BITO appears in the symbol dropdown and can be selected for position tracking. This creates a new cost basis tracking workspace specifically for BITO with empty position groups ready to receive transaction data.
With BITO added as a tracked symbol, the next step records the original cash-secured put that ultimately led to this assignment. The transaction details from ThinkOrSwim transfer directly into MyATMM:
| Field | Value | Source |
|---|---|---|
| Start Date | April 1st | Execution date from statement |
| Action | Sell to Open | Cash-secured put = sell to open |
| Type | Put | Option type |
| Contracts | 1 | Number of contracts sold |
| Expiration | April 5th | Friday expiration |
| Strike Price | $32.00 | Strike where put was sold |
| Premium | $1.86 per share | $186 total premium received |
After entering these values and clicking Save, MyATMM moves the position from the draft area into the "Puts" group and automatically generates a proposed transaction record in the temporary work area.
MyATMM's proposed transaction system provides pre-calculated helper records that streamline final transaction entry. When you save a position, the system automatically:
The demonstration shows the initial proposed record had fees of $0.01, but checking the ThinkOrSwim statement revealed actual fees were $0.02. Using the number picker control, the fees field is adjusted up by one penny to match the broker's actual charges. This attention to precise fee matching ensures perfect balance reconciliation.
Once commissions and fees are verified, clicking the blue calculation button performs the math: $1.86 premium minus $0.65 commission minus $0.02 fees equals $1.19 net credit per share, or $119 total for one contract. This calculated amount populates the permanent transaction record automatically.
The toggle button indicating whether the transaction involves stock or options shows "unchecked" (false) since this is an option transaction, not a stock purchase. With all fields verified, clicking the Save button adds this transaction to the permanent transaction history.
Upon saving, MyATMM immediately updates the summary metrics showing credits received, and all position calculations refresh to include this premium in cost basis adjustments. The demonstration shows deleting and re-adding the transaction to illustrate how the summary totals dynamically update, confirming the integration between permanent transaction history and real-time summary calculations.
With the original cash-secured put recorded, the next step processes the assignment itself, which converts the option obligation into actual stock ownership and updates position metrics accordingly.
MyATMM provides a dedicated assignment workflow accessed through the dropdown on each active option position. For this cash-secured put that expired in the money, selecting "Assigned" from the dropdown opens the assignment entry form with specific fields for processing stock assignments.
The assignment entry requires:
It's important to understand that the assignment price equals the strike price where you originally sold the put, not the current market price. You're obligated to buy shares at $32 even though the market trades at $29, which is precisely why the put buyer exercised the option and assigned it to you.
Clicking Submit on the assignment form triggers MyATMM to perform several automatic operations:
The demonstration shows that after clicking Submit, the stocks position group expanded from zero to one position, with the new BITO stock record appearing. The proposed transactions area also received a new record showing the stock purchase details.
An important detail for option assignments: most brokers including ThinkOrSwim charge zero commissions and zero fees for stock assignments resulting from option exercises. The transaction records simply show the $3,200 stock cost with no additional charges.
This differs from voluntary stock purchases where you'd typically pay commissions. For assignments, the commission was already collected when you sold the original put option, and no additional fees apply when that option gets exercised and stock is delivered to your account.
In the MyATMM proposed transaction record for the stock assignment, both commission and fees fields show $0.00, which is correct and matches the ThinkOrSwim statement.
The proposed transaction system generated all the necessary information for the stock purchase. Notice that for stock transactions, the toggle indicator automatically switched to "true" (checked), indicating this is a stock purchase rather than an option transaction.
The helper system populated:
Clicking the Save button moves this record from proposed transactions into permanent transaction history. The system immediately recalculates all position metrics to reflect the new share ownership and updated cost basis.
After recording both the cash-secured put and the subsequent stock assignment, MyATMM displays comprehensive position metrics that reveal the complete economic picture of your BITO position.
With 100 shares purchased through assignment at $32 per share, the raw cost basis calculation is straightforward:
However, the stock cost alone doesn't tell the complete story. The premium collected from selling the cash-secured put that led to this assignment must be factored into the true economic cost basis.
The cash-secured put generated $185 in net credit after commissions and fees ($186 premium minus $0.65 commission minus $0.02 fees = $185.33 net). This premium reduces the effective cost of the stock acquisition:
| Component | Amount |
|---|---|
| Stock Purchase Cost | $3,200.00 |
| Premium Collected | -$185.33 |
| Net Capital Deployed | $3,014.67 |
| Cost Basis with Premium | $30.15 per share |
This $30.15 premium-adjusted cost basis represents your true breakeven price. While you paid $32 per share for the stock, the $1.85 per share in premium already collected means you need the stock to recover only to $30.15 to break even economically, not $32.
At the time of recording with BITO trading at $29 per share, the position showed:
The premium collection reduced what would have been a $300 paper loss down to $114.67, cutting the unrealized loss by more than 60%. This demonstrates the protective cushion that option premium provides against adverse price movement in the underlying stock.
The demonstration notes that initially the overall gain/loss showed as -$3,200 because MyATMM hadn't yet pulled in the current BITO price. Navigating away from the cost basis page to the dashboard and then returning triggered the price update mechanism.
After the price update, the unrealized loss refreshed to show the actual -$249 value, and the overall position showed slightly negative because the unrealized loss exceeded the premium credits collected to that point. This real-time price integration allows you to see current position status without manually entering or updating stock prices.
Once the assignment is recorded and shares are owned, the wheel strategy transitions from pure cash-secured put selling into bilateral premium collection by selling covered calls against the shares while simultaneously selling additional cash-secured puts at lower strikes.
The power of bilateral positioning comes from generating premium regardless of directional movement:
This creates the mathematical advantage where at least one side is guaranteed to win every week since the price can only move in one direction. Either the upside covered call side wins, or the downside cash-secured put side wins, but both sides collect premium regardless of outcome.
With 100 shares owned at $32 cost basis (before premium adjustments), the covered call analysis begins by examining the $32 strike. The ThinkOrSwim analyze tab shows the options chain for the next Friday expiration with the $32 strike offering:
The demonstration shows adding the "Mark" column to the options chain display using the customize function in ThinkOrSwim, eliminating the need to manually calculate the midpoint between bid and ask. This mark price represents the realistic fill expectation for limit orders.
Selling the $32 strike makes strategic sense because:
The order placement process for the covered call:
The covered call order queues for execution when market opens. As a Sunday placement, it won't fill until Monday morning at the earliest, and may require price adjustment if BITO gaps significantly overnight.
With BITO currently trading at $29.51 (as shown in the demo), the cash-secured put analysis looks at the at-the-money strike for optimal premium collection. The $29.50 strike shows:
The demonstration highlights the extrinsic value column, explaining that for out-of-the-money options, the entire premium consists of extrinsic (time) value. Only when options move in-the-money does intrinsic value appear, with extrinsic value declining as the time component shrinks.
The $29.50 strike selection provides:
Following the same order placement workflow:
Now both orders queue: one covered call at $32 strike targeting $29 credit, and one cash-secured put at $29.50 strike targeting $100 credit, for combined potential premium of approximately $129 for the week.
The total collateral involved in both transactions:
If both orders fill at target prices generating $129 combined premium, this represents 2.2% return on the $5,850 in capital committed to these specific transactions over one week. However, the demonstration title references 5.8% ROI, which likely accounts for the combined premium from both the original put assignment transaction ($186) plus the new bilateral positions ($129), totaling approximately $315 in premium against collateral deployed over the multi-week cycle.
After recording all transactions for the assignment cycle, systematic reconciliation confirms that every entry was processed accurately and MyATMM's calculated balances match the broker's actual account values.
The dashboard displays the current brokerage value after all recorded transactions. The demonstration shows comparing this MyATMM-calculated balance against the ThinkOrSwim account statement ending balance to verify exact match.
The account balance decreased from the initial $10,125.25 to $9,815.25 after the stock assignment, representing the $3,200 stock purchase minus the $186 premium collected, plus other account activity. This balance match confirms:
The demonstration makes an important distinction between two different account value metrics visible in ThinkOrSwim:
For this account after the assignment:
MyATMM matches the cash balance rather than net liquidation value because that's the number that represents actual cash flow and deployed capital before considering unrealized gains or losses on stock holdings. This provides the cleaner reconciliation point and more accurately reflects option trading cash flows.
The demonstration emphasizes performing this balance verification after every transaction recording session, not just weekly or monthly. Immediate reconciliation catches data entry errors while the transaction details are fresh and broker statements are open, making corrections simple.
Waiting days or weeks between transaction entry and reconciliation creates situations where you know there's a mismatch but can't easily identify which of dozens of transactions contains the error. Immediate verification after each session maintains data integrity and ensures your cost basis calculations reflect reality rather than accumulated errors.
The assignment handling workflow demonstrates several MyATMM capabilities specifically designed for wheel strategy implementation and systematic position tracking.
The temporary work area that generates proposed transactions with pre-calculated commissions, fees, and net amounts serves multiple purposes:
As demonstrated when deleting and re-adding transactions, MyATMM recalculates position summaries in real-time as transaction history changes. This includes:
These dynamic calculations mean your position status always reflects complete transaction history without requiring manual updates or formula maintenance.
MyATMM provides multiple cost basis views for different decision-making contexts:
| Metric | Calculation | Use Case |
|---|---|---|
| Stock Cost Basis | Total paid for shares ÷ shares owned | Tax reporting, raw acquisition cost |
| Premium-Adjusted Cost Basis | (Stock cost - premium collected) ÷ shares | True economic breakeven price |
| Proposed Cost Basis | Includes active put obligations | Potential future cost if all puts assign |
Each metric serves specific purposes, with premium-adjusted cost basis being most relevant for trading decisions since it shows your actual economic breakeven including all income collected.
When you process an assignment through MyATMM's assignment dropdown:
This automation reduces the manual work from handling assignments while ensuring all data updates consistently across the application.
Successfully managing cash-secured put assignments and transitioning to bilateral premium collection requires systematic transaction recording, thorough cost basis understanding, and disciplined account reconciliation processes.
Implementing covered calls and cash-secured puts simultaneously on the same underlying provides several advantages:
Maintaining accurate position data requires disciplined recording workflows:
Different cost basis metrics serve different purposes:
Understanding which metric applies to each decision prevents emotional reactions to unrealized losses and keeps focus on the systematic premium collection process that drives long-term profitability.
When calculating return on investment for wheel strategy positions:
The 5.8% ROI referenced in the title reflects premium collected relative to capital committed across the multi-week cycle including both the original assignment transaction and subsequent bilateral positions.
Options trading involves significant risk and is not suitable for all investors. Cash-secured put assignments obligate you to purchase shares at the strike price regardless of how far the underlying security has declined, which can result in substantial losses. Covered calls cap your upside potential and provide only limited downside protection equal to the premium received.
BITO is subject to the risks associated with Bitcoin and Bitcoin futures markets, including extreme volatility, regulatory uncertainty, tracking error, and liquidity risk. Bitcoin prices can experience rapid and substantial declines that would result in corresponding losses on BITO shares acquired through assignments.
The 5.8% ROI shown in this demonstration represents specific market conditions and premium levels available at that time. Future returns will vary significantly based on market volatility, strike selection, execution timing, and assignment frequency. Past performance does not guarantee future results.
This content is for educational purposes only and should not be considered financial advice. Always consult with a qualified financial advisor before implementing any options trading strategy.
MyATMM automatically handles assignment tracking, stock purchase recording, premium-adjusted cost basis calculations, and bilateral position management for systematic wheel strategy implementation.
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