Weekly Review: Managing Covered Calls and Cash-Secured Puts Portfolio

Systematic Weekly Portfolio Maintenance

Managing a multi-ticker options portfolio requires consistent weekly maintenance to track expired positions, adjust cost basis, and set up new trades. This comprehensive weekly review demonstrates the complete workflow for maintaining a covered call and cash-secured put portfolio across multiple positions.

Following a systematic weekly review process ensures accurate cost basis tracking, prevents missed opportunities, and maintains clear visibility into all active positions. This article walks through the complete maintenance workflow using real positions across CLOVE, MVIS, RUM, NVAX, and GRAB.

The Weekly Review Process: A Systematic Approach

A proper weekly review follows a specific sequence to ensure nothing gets missed and all positions are properly maintained. The systematic approach makes managing multiple tickers straightforward and prevents tracking errors.

Step 1: Clear Expired Positions

The first step in every weekly review is clearing out options that expired worthless the previous Friday. This updates your active positions and frees up collateral for new trades:

  • Navigate through each ticker in your cost basis tracker
  • Identify expired contracts by checking expiration dates
  • Delete expired worthless options from the position
  • Update share counts to reflect current holdings
  • Recalculate collateral requirements after removing expired puts
Example from CLOVE:

Started with 400 shares, one call contract and two put contracts that expired December 2nd. After clearing the expired options, the position showed clean 400 shares of stock with no active options. Collateral dropped to zero since no puts remained in play.

Step 2: Review Current Cost Basis

Before setting up new trades, you need to know exactly where each position stands. Reviewing cost basis ensures you set strikes that align with your profit targets:

  • Cost basis with premium: Break-even point including all collected premiums
  • Cost basis without premium: Actual cost of shares excluding option income
  • Proposed cost basis: What cost basis will be if active puts get assigned

Why Cost Basis Matters for Strike Selection

Your covered call strike should typically be at or above your cost basis without premium to ensure you profit on the shares if assigned. However, if you've collected substantial premium, you might accept assignment below your share cost basis while still realizing overall profit.

Step 3: Set Up New Covered Calls

After clearing expired positions, it's time to sell new covered calls on your shares. The strike selection depends on your cost basis and market conditions:

  • Check current stock price to assess realistic strike options
  • Target strikes at or above cost basis for profitable assignments
  • Prioritize weekly expirations to maximize premium frequency
  • Go further out in time if weeklies offer insufficient premium
  • Adjust premium expectations by checking bid-ask spreads

Step 4: Sell New Cash-Secured Puts

The final step is playing the opposite side by selling puts below your current position. This bilateral trading strategy generates income whether the stock moves up or down:

  • Select strikes below current cost basis to improve position if assigned
  • Calculate collateral requirements before committing capital
  • Consider spreads when pricing and try for better fills
  • Use multiple contracts strategically based on available capital

Position-by-Position Review: Real Examples

Let's walk through specific positions to see how the weekly review process works with actual trades, strikes, and decisions.

CLOVE: Managing Low-Price Stock Challenges

CLOVE presented an interesting challenge with limited premium available and the stock trading well below cost basis. Here's how to handle difficult positions:

Position Details:
  • Shares: 400 shares
  • Cost basis with premium: $1.79
  • Cost basis without premium: $2.01
  • Current stock price: $1.34
Strategy Implemented:

With stock at $1.34 and cost basis at $2.01, selling a $2.00 strike call offered no premium for nearby expirations. Had to extend three weeks out to December 23rd to get $1 premium on the call. On the put side, sold 2 contracts at $1.00 strike for December 23rd, collecting premium while waiting for price recovery.

Managing Underwater Positions

When stock price is significantly below cost basis, you have two options: sell far out-of-the-money calls with minimal premium while waiting for recovery, or accept a small loss on shares while keeping all premium collected. The bilateral approach of also selling puts continues generating income while potentially averaging down your cost basis further.

MVIS: Playing Both Sides on Small Position

MVIS showed how to manage a smaller position while still generating premium on both sides:

Position Details:
  • Shares: 200 shares (2 contracts worth)
  • Target call strike: $4.00
  • Current stock price: $3.08
Trades Executed:
  • Covered calls: Sold 2 contracts at $4.00 strike expiring December 9th
  • Cash-secured put: Sold 1 contract at $3.00 strike, trying for $0.11 premium (bid $0.07, ask $0.16)

Even with smaller premium amounts on lower-priced stocks, the bilateral strategy continues building position and collecting income. The key is managing expectations and staying consistent with the process.

RUM: Strategic Strike Selection with Wide Spreads

RUM demonstrated how to handle stocks with wider bid-ask spreads and multiple active contracts:

Position Details:
  • Shares: 400 shares total
  • Active positions: 2 call contracts at $12.00 already in play
  • Break-even cost basis: $8.50
  • Profitable exit cost basis: $11.50
New Trades Setup:
  • Additional calls: Sold 2 more contracts at $11.50 strike for $0.10 (trying for better fill on 20-cent spread)
  • Cash-secured put: Sold 1 contract at $8.50 strike for $0.40 (trying for 5 cents better than mid-point on 10-cent spread)

Working Wide Spreads

When options show wide bid-ask spreads (like 20 cents or more), you can often capture better fills by pricing between the bid and ask. Start with a limit order at a better price than the mid-point. If it doesn't fill, you can adjust lower, but frequently you'll get filled at the better price when market conditions shift.

NVAX: The Near-Assignment That Wasn't

NVAX provided an interesting lesson on how option assignment timing works with after-hours price movements:

The Assignment That Didn't Happen:
  • Put strike: $16.50
  • Stock price at market close: $16.52 (safe by 2 cents)
  • Stock price after hours: $16.40 (would have triggered assignment)
  • Result: No assignment because options only exercise based on regular market hours closing price

This situation highlights an important rule: options assignments are based on the closing price during regular market hours, not after-hours prices. While initially confusing to see the stock below the strike after hours without assignment, this creates an opportunity to sell another put at the same strike for additional premium.

NVAX Position Management:
  • Shares: 300 shares
  • Active calls: 3 contracts at $28.00 strike expiring December 16th
  • Cost basis: $28.00 without premium, pulled down from original $39.50 cost
  • New put: Sold 1 contract at $16.00 strike for $0.69, continuing to play the put side while calls remain active

GRAB: Already Playing Both Sides

GRAB showed a position already optimized with active contracts on both sides, requiring no action:

Active GRAB Position:
  • Shares: 200 shares
  • Active calls: 2 contracts expiring December 16th
  • Active puts: 1 contract expiring December 16th
  • Action required: None - both sides already covered for two weeks

When positions already have active contracts on both sides with time remaining, the best action is often no action. Let the current contracts play out before setting up new trades.

Trading Platform Strategy and Transition Planning

This weekly review also addressed an important strategic decision about trading platforms and capital allocation. Understanding platform strengths and commission structures impacts long-term profitability.

The Commission Question

Commission-free trading platforms like Robinhood offer clear advantages for option sellers, especially on lower-priced stocks where $0.65 per contract can meaningfully impact profit margins. However, more sophisticated platforms offer capabilities that may justify the commission costs as your strategy evolves.

When Commission-Free Trading Makes Sense

For stocks trading under $20 where option premiums might be $0.50 to $2.00, avoiding $0.65 per contract saves 10-30% of your premium. This makes commission-free platforms highly attractive for wheel strategy execution on lower-priced stocks.

Transitioning Capital Between Platforms

The strategy outlined in this review involved gradually transitioning capital from commission-free trading back to a more sophisticated platform for additional trading strategies beyond the wheel:

  • Continue active positions: Let current covered calls and puts play out on the commission-free platform
  • Move idle capital: Transfer cash not tied up in collateral to the new platform
  • Maintain tracking discipline: Use MyATMM to track positions across multiple platforms
  • Choose platform by strategy: Use commission-free for wheel strategy, full-featured platform for other approaches

Future Ticker Selection

When moving to a new platform, focus returns to tickers with strong option premium characteristics:

  • Tilray (TLRY): Lower-priced stock with excellent premiums on both calls and puts
  • FUBO: High-volume options with consistent premium opportunities
  • High volume matters: Ensures tight spreads and easy entry/exit

The Power of Cost Basis Tracking

Throughout this weekly review, one tool proved essential: accurate cost basis tracking. Without clear visibility into your true cost basis across all positions, you cannot make informed decisions about strike selection.

Multiple Cost Basis Views

MyATMM tracks three critical cost basis calculations that inform your trading decisions:

  • Cost Basis Without Premium: Your actual share cost, critical for determining if selling at a specific strike creates a gain or loss on shares
  • Cost Basis With Premium: Your break-even point after factoring in all collected option income, showing when you're truly profitable
  • Proposed Cost Basis: Shows what your cost basis will become if active cash-secured puts get assigned, essential for planning
Real Example from NVAX:

Original cost basis started around $39.50. Through consistent put assignments and premium collection, cost basis pulled down to $28.00. Even though current calls are sold at $28.00 (giving up $0.26 per share from cost basis), all the premium collected means overall profit when assignment happens. Plus, continuing to sell puts below market keeps pulling cost basis lower, making future assignment more profitable.

How MyATMM Simplifies Weekly Reviews

A purpose-built cost basis tracker transforms the weekly review process from tedious to systematic:

  • See all positions at a glance instead of hunting through spreadsheets
  • Accurate cost basis calculations automatically update with each transaction
  • Track expired contracts and easily remove them from active positions
  • Calculate collateral requirements instantly when planning new puts
  • View both detail and summary perspectives of your portfolio

Beyond Brokerage Tools

Your brokerage shows your current positions but doesn't track cost basis the way option sellers need it. MyATMM factors in all premium collected, all assignments, and all cost basis adjustments to show you exactly where you stand before making your next trade.

The Bilateral Trading Advantage

This weekly review consistently demonstrated the power of playing both sides of every position. Rather than simply holding shares and selling covered calls, the bilateral approach generates income in both directions.

Why Play Both Sides?

Selling covered calls and cash-secured puts on the same stock creates multiple advantages:

  • Income in any market direction: Collect premium whether stock goes up, down, or sideways
  • Lower average cost basis: Put assignments bring your cost basis down
  • Higher probability of profit: Multiple ways to win on the same stock
  • Collateral efficiency: Use cash reserves to generate put premium instead of sitting idle
Bilateral Trading in Action:

On RUM with 400 shares: Sold 4 covered calls total (2 from previous week still active, 2 new) and sold 1 cash-secured put. If stock goes up, calls profit. If stock goes down, put premium profits and potential assignment improves cost basis. Either direction generates income.

Strike Selection for Bilateral Trading

When playing both sides, strike selection follows clear guidelines:

  • Call strikes: At or above cost basis to ensure profitable assignment
  • Put strikes: Below current cost basis to improve position if assigned
  • Gap between strikes: Wide enough to avoid whipsaw assignments, close enough to generate meaningful premium

The Continuous Improvement Cycle

Each put assignment lowers your cost basis. Lower cost basis means call strikes can be set lower while remaining profitable. Lower call strikes have higher premium and higher probability of assignment. Assignment frees up shares to repeat the cycle.

Portfolio Performance and Expectations

At the time of this review, the portfolio was showing approximately $1,400 unrealized loss, primarily driven by NVAX position. Understanding how to view portfolio performance in the context of an option selling strategy is essential.

Unrealized Loss vs. Income Generation

A common misunderstanding when evaluating wheel strategy performance is focusing solely on unrealized stock losses while ignoring premium income:

  • Unrealized losses reflect current stock prices below purchase prices
  • Realized income from premium collection offsets those paper losses
  • Cost basis improvements through put assignments change the math over time
  • Assignment likelihood increases as cost basis comes down
NVAX as Case Study:

300 shares with cost basis that started at $39.50 and is now at $28.00. Current stock price around $16.50 shows significant unrealized loss, but all the premium collected and cost basis reduction means the position is working as designed. As cost basis continues dropping through put assignments, the stock just needs to recover to low-$20s instead of high-$30s to achieve profitable assignment.

Patience and Consistency

The wheel strategy and bilateral trading approach require patience and consistency:

  • Weekly premium accumulation compounds over months
  • Cost basis improvements happen gradually through assignments
  • Stock recoveries eventually happen on quality stocks
  • Position management beats trying to predict stock direction

Key Takeaways from Weekly Portfolio Review

This comprehensive weekly review demonstrated essential practices for managing a multi-ticker options portfolio:

  • Systematic process prevents mistakes: Following the same sequence each week (clear expired, review cost basis, set calls, set puts) ensures nothing gets missed
  • Cost basis tracking is non-negotiable: You cannot make informed strike decisions without knowing your exact cost basis across all positions
  • Bilateral trading maximizes income: Playing both sides generates premium in any market direction
  • Platform selection matters: Choose platforms based on commission structure and strategy needs
  • Wide spreads offer opportunity: Don't accept the bid-ask midpoint on wide spreads; try for better fills
  • Assignment rules are specific: Options exercise based on regular market hours close, not after-hours prices
  • Patience and consistency win: Weekly premium accumulation and gradual cost basis improvements compound over time

The Foundation of Successful Options Income

A consistent weekly review process combined with accurate cost basis tracking creates the foundation for successful long-term options income generation. The systematic approach demonstrated in this review ensures you maintain control of all positions and make informed decisions every week.

Important Risk Disclosure

Options trading involves significant risk and is not suitable for all investors. Selling covered calls limits upside potential, and selling cash-secured puts requires sufficient capital to purchase shares if assigned. Stock prices can decline below put strikes, resulting in losses. Wide bid-ask spreads can impact entry and exit prices. Past performance does not guarantee future results.

This content is for educational purposes only and should not be considered financial advice. Every trader's situation is different. Always conduct your own research and consider consulting with a qualified financial advisor before implementing any options strategy.

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