After placing option trades, the real work of portfolio management begins. Every covered call sold and every cash-secured put opened represents a transaction that must be tracked accurately to maintain true cost basis visibility. Without systematic entry of these transactions into a tracking platform, you're flying blind when making future trade decisions.
This detailed tutorial walks through the complete workflow for entering Robinhood option transactions into MyATMM. From downloading transaction history to logging individual options to accounting for potential assignments, this process ensures your cost basis calculations remain accurate across all positions.
The session demonstrates real transactions across multiple tickers—CLOV, GRAB, MO, MVIS, NVAX, RIG, and RUM—showing how to handle different scenarios including multi-contract positions, varying expiration dates, and collateral allocation for open puts. Each ticker receives systematic treatment following the same repeatable process.
Robinhood doesn't provide an easy-to-use transaction export feature natively. The platform shows individual trades in your history, but organizing multiple transactions for systematic entry requires a better approach.
A Chrome extension called "Robinhood Transaction History Downloader" solves this problem. Search for it in the Chrome Web Store and install it. This tool adds a download button to your Robinhood account history page.
When you click the download button, the extension exports all recent transactions to a CSV file that can be opened in any spreadsheet program. This spreadsheet format makes it dramatically easier to review what executed and prepare for systematic entry into MyATMM.
The downloaded CSV contains all transaction types—stocks, options, dividends, fees. For option tracking purposes, filter to show only option transactions. Then sort by ticker symbol to group all transactions for the same underlying together.
This sorting step is crucial. When you're ready to enter transactions into MyATMM, you'll work ticker by ticker. Having all CLOV transactions together, then all GRAB transactions, then all MO transactions creates an efficient workflow.
The transaction history CSV shows gross premium amounts but doesn't always include exact fees and commissions. Robinhood charges small fees (often a few cents per contract) that slightly reduce your actual net credit.
For perfect accuracy, you'll need to access the official trade confirmations in your Robinhood account (available the business day after each trade executes). These PDF documents show the exact net credit after all fees. Most traders update their MyATMM entries later with these precise figures, accepting that initial entries will be slightly off by pennies.
With your organized transaction spreadsheet ready, begin systematic entry into MyATMM. The process follows a consistent pattern for every ticker.
In MyATMM, navigate to the cost basis page and select the ticker you're updating. The cost basis page displays all existing positions, current share count, cost basis metrics, and the transaction history for that ticker.
Before entering any transaction, verify it hasn't already been logged. Check the transaction date on your spreadsheet against the dates in MyATMM's transaction history. If you see a matching date and premium amount, skip that transaction—it's already recorded.
This verification step prevents duplicate entries that would throw off your cost basis calculations. It's especially important when you've had interruptions in your tracking workflow and aren't certain what's been entered already.
Click "New Position" or the equivalent button to add a transaction. MyATMM presents a form for entering the details:
Fill in each field carefully from your spreadsheet data. The platform calculates total premium automatically based on price per share and contract count, but verify the calculation matches your spreadsheet.
After entering all details, save the transaction. MyATMM creates a draft position. Review the draft for accuracy, then move it to the permanent transaction history by clicking the save icon.
Watch the cost basis numbers as you move transactions to history. You'll see the cost basis per share decrease slightly as each premium gets factored into the calculation. This real-time feedback confirms that premium collection is actively reducing your breakeven point.
When you enter a cash-secured put, you're committing to potentially purchase shares at the strike price. MyATMM allows you to account for this potential assignment by adjusting your position's share count and collateral.
For example, if you sold one $3 put and already own 200 shares, update to show 300 shares with $300 additional collateral ($3 strike × 100 shares). This shows your proposed cost basis—what your cost basis would become if the put is assigned.
If the put expires worthless, simply revert those numbers back to the original 200 shares. The temporary adjustment helps you understand the impact of potential assignments before they happen.
Walking through actual examples across different tickers demonstrates how the process handles various scenarios.
Two transactions executed on CLOV:
Entry process for the put: Select "Sold to Open," choose "Put," enter 2 contracts, set expiration to December 2, strike price $1, price $0.02. Premium automatically calculates to $4. Save and move to transaction history.
Before moving to history, note the current cost basis. After moving to history, watch it decrease by a few cents as the $4 premium factors into the calculation.
Next, account for collateral. The two put contracts represent potential purchase of 200 shares at $1 each = $200 collateral. Update share count from 400 to 600 and add $200 to collateral. This shows proposed cost basis if the puts assign.
Repeat the same process for the call. The call premium further reduces cost basis. Since calls are covered by existing shares, no collateral adjustment needed.
GRAB transaction: Sold 2 contracts, $3 strike, November 25 expiration, $0.05 per share = $10 total premium.
Entry follows the same pattern: Sold to Open, Put, 2 contracts, November 25 expiration, $3 strike, $0.05 price. Save and move to history. Watch cost basis decrease by approximately $0.05 per share as the $10 premium spreads across the existing share count.
Account for collateral: 2 contracts × 100 shares × $3 strike = $600 potential commitment. Update share count by 200 and collateral by $600 to reflect proposed position if assigned.
MO transaction: Sold 1 contract, $46 strike, November 25 expiration, $0.01 per share = $1 total premium.
This represents a very conservative covered call far above the current stock price. The minimal premium ($1) barely moves the cost basis, but it's free money for taking essentially no assignment risk. Entry process identical: Sold to Open, Call, 1 contract, November 25 expiration, $46 strike, $0.01 price.
After moving to history, cost basis decreases by about one penny per share. Not substantial, but it demonstrates that even small premiums compound over time when executed consistently.
RUM had the most complex activity with four separate transactions:
| Type | Contracts | Strike | Expiration | Premium |
|---|---|---|---|---|
| Put | 1 | $10 | Nov 25 | $95 ($0.95/share) |
| Call | 1 | $12.50 | Dec 2 | $10 ($0.10/share) |
| Call | 1 | $13 | Nov 25 | $5 ($0.05/share) |
| Put | 1 | $8 | Nov 25 | $15 ($0.15/share) |
Each transaction gets entered individually following the same systematic process. The $10 put at $0.95 premium represents excellent income—$95 for committing to buy 100 shares at $10. The various calls at different strikes demonstrate a layered approach to selling premium.
After entering all four transactions, collateral accounting becomes important. Two puts are open: one at $10 strike (100 shares, $1,000 collateral) and one at $8 strike (100 shares, $800 collateral). Total collateral: $1,800 representing potential purchase of 200 additional shares.
Update the position to reflect this: increase share count by 200, increase collateral by $1,800. The proposed cost basis updates to show what would happen if both puts assign. This forward-looking view helps evaluate whether accepting assignment at these strikes supports overall strategy goals.
MyATMM calculates two different cost basis figures, each serving a distinct purpose in your trading decision-making.
This represents your average share purchase price ignoring all premium collected. If you bought 100 shares at $30, 100 shares at $28, and 100 shares at $26, your simple cost basis is $28 (the average of your purchase prices).
This number tells you what you actually paid for shares. It's useful for understanding your stock investment but doesn't reflect the complete picture of your position profitability.
This represents your true breakeven point after accounting for all premium collected. Using the same example, if you collected $600 in total option premium on those 300 shares, your premium-adjusted cost basis would be $26 ($28 simple cost basis minus $2 in premium per share).
This number is critical for trade planning. When selecting strike prices for covered calls, compare strikes to this premium-adjusted cost basis. Selling calls above this level ensures you'll profit even if assigned. Selling calls below this level means assignment would result in a net loss despite all the premium collected.
Early in the session, the trader mentions initially targeting cost basis with premium when selecting strikes for new positions. This created a pattern of breaking even repeatedly—positions would get assigned near the premium-adjusted cost basis, resulting in no net gain or loss.
The realization: target the simple cost basis (without premium) when selecting strike prices. This ensures that when assigned, you profit from both the stock appreciation and keep all the premium collected. The premium becomes pure profit on top of the stock gain.
Simple Cost Basis (without premium): $28.26 per share
Premium-Adjusted Cost Basis: $23.58 per share (after $2,959 total premium collected)
Total Shares: 300
Current Stock Price: $19.45
Unrealized Loss: -$7,505 (on paper)
True Position Status: Need stock to reach $23.58 to break even (not $28.26)
Strike Selection: Selling $26 calls allows for profit if assigned ($26 is above $23.58 breakeven but below $28.26 simple cost basis)
This example shows how premium collection creates a dramatically different breakeven point. On paper, the position shows a massive loss. In reality, the position needs far less price appreciation to become profitable thanks to the $2,959 in collected premiums.
Selling cash-secured puts provides a paid form of dollar cost averaging. Instead of buying shares outright at current prices, you get paid to commit to buying shares at lower prices if the stock drops.
If assigned, you acquire shares at your chosen strike price minus the premium collected. If not assigned, you keep the premium and can sell another put. Either outcome is acceptable, creating a win-win scenario that traditional stock purchases don't offer.
Over time, this strategy pulls your cost basis down systematically. Each assignment adds shares at progressively lower effective costs (strike minus premium). Eventually, you can sell covered calls at strikes that offer substantial premium because they're still above your deeply reduced premium-adjusted cost basis.
After completing transaction entry, the MyATMM dashboard provides comprehensive position metrics and premium tracking across all tickers.
The dashboard includes a dedicated Premiums tab that groups all option income by month and year. This view shows total premiums received for each time period, creating a clear picture of strategy effectiveness over time.
Before entering the session's transactions, the November premium total was around $1,200. After entering all the week's executed trades, it increased to $1,551. This $350+ increase represents one week's systematic execution across the portfolio.
Comparing month to month reveals patterns and trends. Are you generating more premium as positions grow? Are certain months historically better for your tickers due to seasonal volatility patterns? The monthly breakdown makes these patterns visible.
The dashboard displays what percentage of your total capital is not currently working for you. This includes cash sitting idle and shares not currently covered by any options.
For cash flow investors, keeping this percentage low is ideal. You want as much capital as possible deployed in income-generating positions. A high unused capital percentage suggests opportunity for additional option positions or strategic share purchases.
The positions view shows each ticker's percentage of total portfolio value, current profit/loss status, and key metrics. This creates visibility into concentration risk and helps identify which positions are performing well versus those needing attention.
Seeing multiple positions in the red (negative unrealized P&L) can be discouraging, but the premium collection numbers provide the complete story. A position showing -$7,500 unrealized loss might have generated $3,000 in premium, making the true loss only -$4,500.
MyATMM displays two account balance figures: your actual brokerage account balance and the calculated balance based on all tracked transactions. These numbers should match exactly.
If they don't match, it indicates a missing or incorrectly entered transaction. This reconciliation feature serves as a critical error-checking mechanism, ensuring your tracking remains accurate as complexity increases across multiple tickers and hundreds of transactions.
The detailed transaction entry process might seem tedious, especially when dealing with dozens of small premium transactions across multiple tickers. The temptation to skip this step or delay it is strong. Resist that temptation.
Without accurate tracking of every transaction, you're making trading decisions based on incomplete information. You might think your cost basis is $30 when it's actually $27 after premium adjustments. That $3 difference dramatically changes which strike prices make sense for new covered calls.
Systematic tracking transforms subjective feelings about your positions into objective data. Instead of wondering if your strategy is working, you have concrete evidence in the form of premium totals, cost basis trends, and position-level profitability.
Many traders start with spreadsheets for tracking option trades. For one or two tickers with monthly options, this works adequately. When you scale to five tickers with weekly options, selling both calls and puts, tracking assignments, and managing rolling positions, spreadsheets become unmanageable.
Formula errors creep in. Missing transactions break calculations. Different spreadsheet versions create confusion about which is current. The administrative overhead of maintaining accurate spreadsheets eventually exceeds the time available for actual trading.
Purpose-built platforms like MyATMM solve this scaling problem. The structured transaction entry ensures consistency. Automatic calculations eliminate formula errors. Centralized storage prevents version confusion. The platform handles the complexity so you can focus on trading decisions.
When tax season arrives, you'll need accurate records of every option transaction, every assignment, every premium collected. Brokerages provide 1099 forms with aggregate totals, but understanding your actual profit/loss by position requires detailed tracking.
Having a complete transaction history for the entire year makes tax preparation straightforward. You can generate reports showing total premium by ticker, capital gains from assignments, and cost basis for any remaining shares. Without this documentation, tax season becomes a nightmare of reconstructing trades from incomplete brokerage statements.
Individual small premiums—$4 here, $10 there, $50 on another trade—don't feel significant in isolation. The systematic tracking reveals their compounding effect. That $1,551 monthly premium total represents hundreds of dollars in income generated from a portfolio requiring minimal active management time.
Seeing the cumulative totals provides psychological reinforcement that the strategy works. On down days when stock prices drop and unrealized losses increase, the growing premium totals remind you that the cash flow strategy is still functioning exactly as designed.
MyATMM displays a "Principle Left" metric in red for each position. This important number represents capital still at risk in the position.
Principle Left equals current stock value minus total premium collected. If you own 1,000 shares at $20 current price ($20,000 total value) and have collected $3,000 in premium, your Principle Left is $17,000.
This number is displayed in red because it represents capital at risk. If the stock went to zero, you'd lose this entire amount. The premium you've collected provides a cushion against loss, but it doesn't eliminate risk entirely.
The ultimate goal is collecting enough premium over time that Principle Left reaches zero or goes negative. At that point, you own the stock "for free" in the sense that total premium collected equals or exceeds current stock value.
This doesn't mean you're risk-free—the stock can still decline, reducing the value of what you own. But it means all your original capital has been recovered through premium collection. Any future stock value is pure profit.
Reaching this point requires extended time in a position with consistent premium collection. It's more achievable with higher-volatility stocks that offer larger premiums relative to stock price. Lower-volatility blue chips take longer to achieve this status.
The red color serves as a constant reminder that this capital remains at risk. It prevents complacency about positions just because you're collecting consistent premium. Until Principle Left reaches zero, meaningful downside risk exists.
When evaluating new positions or deciding whether to add capital to existing positions, check Principle Left across your portfolio. If most positions show high Principle Left relative to total value, adding more capital increases overall risk. If several positions have low or negative Principle Left, adding new capital to build additional positions becomes more palatable.
Position: RUM (Rumble)
Shares Owned: 400
Current Price: $10.50
Current Stock Value: $4,200
Total Premium Collected: $1,000
Principle Left: $3,200 (displayed in red)
Interpretation: If RUM went to zero, maximum loss would be $3,200 (not $4,200) because $1,000 in premium has already been collected. Need to collect $3,200 more in premium to own the position "for free."
The detailed workflow demonstrated in this tutorial—extracting Robinhood transaction data, systematically entering each option trade, accounting for collateral on open puts, and verifying cost basis calculations—represents the foundation of successful cash flow investing.
This process takes 15-30 minutes after each week's trading activity. That modest time investment creates comprehensive visibility into position status, cost basis accuracy, premium collection totals, and capital deployment efficiency. Without this tracking, you're operating on assumptions rather than data.
The Robinhood transaction history downloader Chrome extension makes the first step straightforward—exporting recent trades into an organized spreadsheet. Sorting that data by ticker symbol creates the structure needed for efficient entry. Taking the time to verify no duplicate entries exist prevents tracking errors that compound over time.
MyATMM's structured transaction entry forms guide you through capturing every relevant detail: contract count, strike price, expiration date, premium amount. The platform calculates total premium automatically and shows real-time cost basis updates as each transaction moves from draft to permanent history.
Accounting for collateral on open cash-secured puts provides forward-looking visibility. You can see proposed cost basis before puts assign, helping evaluate whether accepting assignment at those strikes supports overall strategy goals. This forward-looking perspective enables proactive position management rather than reactive scrambling.
The two cost basis figures—simple and premium-adjusted—tell complementary stories about position status. Simple cost basis shows average purchase price. Premium-adjusted cost basis shows true breakeven after all premium collection. Understanding both numbers and using them appropriately for strike selection decisions separates successful option sellers from those who constantly struggle to generate consistent profits.
Dashboard metrics provide the 30,000-foot view of portfolio status. Monthly premium totals demonstrate strategy effectiveness. Unused capital percentages identify deployment opportunities. Position breakdowns reveal concentration risk. Account reconciliation catches errors before they compound. These aggregated metrics turn individual transaction details into actionable portfolio insights.
Build the tracking habit now, while portfolio complexity remains manageable. As you add tickers, increase contract counts, and begin rolling positions frequently, the organizational foundation created by systematic tracking becomes essential infrastructure. Without it, scaling becomes impossible. With it, managing dozens of weekly positions across multiple tickers becomes routine.
The 15-30 minutes spent on tracking each week isn't overhead—it's an investment in strategy sustainability. The alternative is flying blind, making decisions based on guesses, and eventually hitting a complexity wall that forces you to abandon systematic option selling altogether. Choose systematic tracking. Your future self will thank you.
Options trading involves significant risk and is not suitable for all investors. Selling cash-secured puts obligates you to purchase shares at the strike price, potentially resulting in losses if the stock declines significantly. Covered calls cap upside potential and provide limited downside protection only to the extent of premium received.
Accurate tracking and cost basis calculation do not eliminate market risk or guarantee profitability. Stock prices can decline below any cost basis, including premium-adjusted figures. The strategies discussed require sufficient capital, risk tolerance, and understanding of option mechanics.
This content is for educational purposes only and should not be considered financial advice. Consult with qualified financial professionals before implementing any options trading strategy.
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