After placing cash-secured put orders, the next critical step is accurately logging those transactions into your cost basis tracking system. This follow-up process can make or break your ability to maintain precise records and understand your true portfolio performance over time.
In this comprehensive guide, we'll walk through the complete workflow for recording cash-secured put transactions from ThinkOrSwim (TD Ameritrade) into MyATMM's cost basis tracking platform. You'll discover why the transaction history feature in ThinkOrSwim provides a significant advantage over other brokerages, saving valuable time and preventing reconciliation errors.
This tutorial covers the actual logging process for three cash-secured put positions: NVAX, RUM, and TLRY. We collected over $200 in premium for the week, and you'll see exactly how each transaction gets recorded with pre-calculated fees, eliminating the need for manual reconciliation later.
One of the most frustrating aspects of tracking options trades is dealing with brokerage fees. Some platforms make you wait until the next day to download confirmation PDFs, forcing you to manually update your records multiple times for the same transaction.
ThinkOrSwim (TD Ameritrade) solves this problem with its transaction history feature. When you access your transaction history from the Ameritrade website, the system automatically calculates and deducts all fees from your premium amounts before displaying the final numbers.
When you log a transaction with ThinkOrSwim's pre-calculated amounts, the number you enter is the final number. You won't need to reconcile anything or go back to adjust for fees after downloading confirmation documents. This "set it and forget it" approach dramatically reduces administrative overhead.
With Robinhood and similar platforms, traders often rely on browser plug-ins like the "Robinhood Transaction History Downloader" to export data to CSV format. While helpful, these tools typically only capture the initial premium collected or the gross transaction cost. They don't automatically factor in fees.
This creates a two-step reconciliation process:
ThinkOrSwim eliminates steps 2-4 entirely. The amount you see in the transaction history is the amount that actually hit your account, fees already deducted.
Let's walk through the actual process of logging three cash-secured put transactions: TLRY, NVAX, and RUM. Each follows the same efficient workflow using MyATMM's cost basis tracking system.
The first transaction involves selling two put contracts on Tilray (TLRY). Here's the complete transaction data:
| Detail | Value |
|---|---|
| Position Type | Sell to Open PUT |
| Number of Contracts | 2 |
| Expiration Date | December 16, 2022 |
| Strike Price | $3.50 |
| Premium Per Contract | $0.25 |
| Gross Premium | $50.00 |
| Net Premium (After Fees) | $48.68 |
Important Note on Position Filtering: When logging this transaction in MyATMM, the ticker TLRY doesn't initially appear when filtering by "positions only" because there are currently no active positions. The filter must be removed to access tickers that have been traded previously but don't currently have open positions.
In MyATMM, we add a new position for TLRY, selecting "Sell to Open" with position type "PUT." After entering 2 contracts at $3.50 strike expiring December 16th, the system initially calculates $50.00 as the premium credit.
However, we don't save this proposed amount. Instead, we immediately edit the transaction record to reflect the actual net premium of $48.68 from the ThinkOrSwim transaction history. Once saved with the correct amount, the transaction is complete with no future reconciliation needed.
The system automatically updates the collateral requirement and calculates the proposed cost basis assuming assignment. Since no shares are currently owned, there's no cost basis with or without premium yet—that will only appear if the puts get assigned.
The second position involves Novavax (NVAX), a stock that has been actively traded with cash-secured puts for several consecutive weeks:
| Detail | Value |
|---|---|
| Position Type | Sell to Open PUT |
| Number of Contracts | 1 |
| Expiration Date | December 16, 2022 |
| Strike Price | $16.50 |
| Premium Per Contract | $1.09 |
| Gross Premium | $109.00 |
| Net Premium (After Fees) | $108.34 |
This marks the third consecutive week selling a cash-secured put on NVAX at or near the $16.50 strike. Each previous week, the put expired worthless, allowing the premium to be pocketed without assignment.
The cost basis currently sits at $28.26 per share without premium, representing 300 shares already owned. If this put were assigned, it would bring the total position to 400 shares and lower the cost basis to $25.50 per share.
More importantly, the cumulative premium collected across all NVAX transactions totals $1,884.74. This means that even if all shares were sold at break-even with no capital gains, the position would still be profitable by nearly $1,900 purely from premium income.
The final transaction covers Rumble (RUM), a position that has accumulated shares over time while the stock price has declined:
| Detail | Value |
|---|---|
| Position Type | Sell to Open PUT |
| Number of Contracts | 1 |
| Expiration Date | December 16, 2022 |
| Strike Price | $7.50 |
| Premium Per Contract | $0.25 |
| Gross Premium | $25.00 |
| Net Premium (After Fees) | $24.34 |
RUM presents an interesting case study in managing a declining stock position through consistent premium collection. The current cost basis sits at $10.70 per share, while the stock is trading around $8.05. However, the cost basis with premium factored in is $8.23, much closer to the current market price.
The proposed cost basis (accounting for the active cash-secured put) would be $10.17 per share if assigned. While this represents an unrealized loss at current market prices, the consistent premium collection continues to lower the cost basis over time.
RUM demonstrates a patient, income-focused approach to managing positions that have declined in value. Rather than selling for a loss or holding without generating income, continuing to sell cash-secured puts accomplishes multiple goals:
As the position accumulates more shares, the cost basis lowers more slowly due to the larger share count. However, the willingness to hold long-term and continue collecting premiums makes this a viable strategy for stocks you're comfortable owning.
After logging all three transactions, it's valuable to review the total premium collected. MyATMM makes this easy through the Dashboard's Premiums tab, which aggregates all premium income across all positions.
For the week covering these transactions, the total premium collected from ThinkOrSwim positions was:
| Transaction | Premium (After Fees) |
|---|---|
| TLRY - 2 Contracts | $48.68 |
| NVAX - 1 Contract | $108.34 |
| RUM - 1 Contract | $24.34 |
| Robinhood Positions | ~$50.00 |
| Total Weekly Premium | $231.36 |
| Month-to-Date (December) | $455.21 |
These numbers represent actual deposited amounts after all brokerage fees. The month-to-date figure of $455.21 reflects consistent weekly cash-secured put selling across multiple positions and brokerages.
Generating over $200 per week in premium income might not seem extraordinary on its own, but the consistency is what makes this strategy powerful. Annualized, this weekly rate represents over $12,000 in income purely from option premium collection.
This income stream exists regardless of whether stocks go up, down, or sideways. It provides portfolio cushion during downturns, accelerates gains during uptrends, and generates returns during stagnant markets. The key is maintaining accurate records so you can calculate true returns and make informed trading decisions.
The transaction logging process demonstrated in this tutorial might seem like basic data entry, but it serves critical functions for options traders:
Your brokerage account might show unrealized losses on certain positions, but those numbers don't include all the premium you've collected over time. By tracking cost basis with premium factored in, you can see your true profit/loss picture and make informed decisions about when to close positions or continue trading them.
Knowing your exact cost basis helps you select appropriate strike prices for covered calls. If your cost basis is $25.50 but your brokerage shows $28.26, you might unnecessarily avoid selling calls at $26 or $27 strikes that would actually be profitable when accounting for collected premium.
When cash-secured puts approach expiration, deciding whether to roll or accept assignment depends on understanding what your new cost basis would be. MyATMM's "proposed cost basis" feature shows exactly what your cost basis would become if active puts get assigned, helping you make strategic decisions.
Accurate records of every transaction, including the exact premium collected after fees, makes tax preparation significantly easier. You'll have a complete audit trail of all trades, premiums, assignments, and resulting cost basis adjustments.
Understanding the total premium collected on positions helps you evaluate risk tolerance. A position showing an unrealized loss might be psychologically easier to hold when you can see that cumulative premium has already offset most or all of that loss.
While the transaction logging workflow demonstrated here is straightforward, MyATMM includes several features that make the process even more efficient:
When you enter a cash-secured put position, MyATMM automatically calculates the required collateral based on the strike price and number of contracts. You don't need to manually compute that you need $700 in buying power to secure a $7.50 put—the system does it for you.
Before your puts get assigned, you can see exactly what your cost basis would become. This "what-if" analysis helps you decide whether to roll positions or accept assignment based on how it affects your overall cost basis.
The Dashboard's Premiums tab aggregates all premium collected across all positions and time periods. You can instantly see daily, weekly, monthly, and annual premium totals without creating complex spreadsheet formulas or manually adding up transaction history.
Toggle between viewing all tickers you've ever traded versus only active positions with current holdings. This flexibility helps you navigate large portfolios while keeping historical data accessible for reference.
Every recorded transaction remains in the system, creating a complete audit trail. You can review past trades, verify premium amounts, and analyze your trading history to identify patterns and improve your strategy.
Unlike general portfolio trackers or spreadsheets, MyATMM is purpose-built for traders who sell covered calls and cash-secured puts. Every feature is designed specifically to address the cost basis tracking challenges that option sellers face, making it the ideal alternative to manually maintaining complex spreadsheets.
To maintain accurate records and minimize future reconciliation work, follow these best practices when logging cash-secured put transactions:
Don't let transactions accumulate. Log them the same day they execute, preferably right after accessing your brokerage's transaction history. This prevents missing trades and ensures your cost basis tracking stays current.
Never log the gross premium shown in your order confirmation. Always wait for the transaction history to show the net amount after fees, then log that exact number. This eliminates reconciliation work later.
Double-check expiration dates when logging positions. A typo here could cause confusion when options expire and you're trying to determine which positions closed and which remain active.
After saving a transaction, take a moment to review how it affected your cost basis. Make sure the numbers make sense relative to your existing position. This quick sanity check can catch data entry errors before they compound.
Periodically compare your tracking system's premium totals against your brokerage statements. They should match (accounting for timing differences if logging trades the same day). Significant discrepancies indicate missed transactions or data entry errors.
While not strictly necessary if you log transactions accurately, keeping screenshots of your brokerage's transaction history provides backup documentation for tax purposes and helps resolve any disputes about executed trades.
Options trading involves substantial risk and is not suitable for all investors. Cash-secured puts obligate you to purchase shares at the strike price if assigned, which could result in losses if the stock declines significantly. Past performance does not guarantee future results. The examples shown represent actual trades but should not be interpreted as typical results or recommendations. Always consider your risk tolerance, investment objectives, and financial situation before trading options. This content is for educational purposes only and should not be considered financial advice. Consult with a qualified financial advisor before making investment decisions.
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