You've read about cash-secured puts. You understand the mechanics. You know the risks. Now you want to actually do it.

This guide walks you through the entire process on Interactive Brokers—from logging in to executing your first trade. It's the bridge between theory and practice.

Pre-Flight Checklist: Before You Log In

1. Verify Your Account Type Supports Options

Not all Interactive Brokers accounts can trade options. You need at least:

Account type: Individuals accounts work. Company/trust accounts may have restrictions.
Account status: Account must be fully opened (not pending verification)
Options level: You need "Level 2" options approval minimum (CSPs are Level 2)

To check:

Log into Trader Workstation (TWS)
Go to Account → Account Settings
Scroll to "Options Approval" section
Confirm: "Level 2 - Covered Calls & Protective Puts" or higher

If you have Level 1, you'll need to upgrade. Go to the "Profile" section and request an upgrade.

2. Ensure You Have the Right Cash

Cash-secured puts require a cash buffer equal to the strike price × 100.

Example: You want to sell a $100 strike put. You need $10,000 in cash available.

Check your cash:

TWS home screen, look at "Account Summary"
Find "Cash (USD)" or "Available Funds"
Confirm you have enough for your trade + 10% buffer (in case of margin calls)

Pro tip: IB allows margin. But for CSPs, you typically need to reserve the full strike price in cash. Some brokers require 20-30% down if you accept margin. We'll assume you're using cash for simplicity here.

3. Choose Your Broker Platform

Interactive Brokers has multiple platforms:

Trader Workstation (TWS): Desktop app (most powerful, complex)
Mobile App: Simple, limited features
Web Portal: Middle ground

For selling puts, use TWS. It has the best options chains and order entry tools.

Step 1: Open the Options Chain

Via Trader Workstation Desktop

Log into TWS
Search for a stock (e.g., "MSFT" for Microsoft)
- Use the top search bar or click "Quote" tab
Right-click on the stock → Select "Option Chain"
A new window opens with the options chain

You'll see:

Calls (Left Side)                 | Stock/Details (Center) | Puts (Right Side)
Strike | Bid-Ask | Implied Vol    |  MSFT = $427           | Implied Vol | Bid-Ask | Strike
...
230    | 197-200 | 1.2%           |                        | 0.8%       | 200-205 | 210
...
420    | 7.20-7.50 | 22%          |                        | 18%        | 0.80-1.10 | 410
...
430    | 2.00-2.20 | 20%          |                        | 18%        | 1.50-1.80 | 420

The right side shows puts. This is what you care about for selling.

Reading the Puts Column

From right to left:

Implied Vol (IV): How much the market expects the stock to move
Bid-Ask: The spread—bid is what buyers will pay to buy, ask is what sellers will receive to sell
Strike: The price at which you're selling the put

Step 2: Pick Your Expiration Date

The options chain shows multiple expiration dates along the top. Common choices:

Weekly: Expires next Friday (usually 0-7 days out)
Monthly: Expires 3rd Friday of next month (usually 30-45 days)

For your first trade, pick monthly (less stressful than weekly).

Click on the monthly expiration (e.g., "Nov 21" for third Friday in November).

The chain updates to show puts expiring on that date.

Step 3: Choose Your Strike

Now you're staring at rows of strikes. Which one to pick?

The key question: "At what price would I be comfortable owning this stock?"

Example: MSFT is trading at $427. You'd be happy to own it at $410 (a ~3.8% discount).

Scan down the Strike column on the right until you find $410 (or close to it).

You'll see something like:

Puts
Implied Vol | Bid-Ask | Strike
18%         | 2.10-2.40 | 410

This means:

Bid: $2.10 → Brokers will buy this put from you for $2.10/share
Ask: $2.40 → Brokers will sell this put to you for $2.40/share
Implied Vol: 18% → Market expects ~18% annualized volatility

Step 4: Calculate Your Return

Before you sell, calculate what you're actually getting.

Formula:

Annualized ROI = (Premium / Strike Price) × (365 / Days to Expiration) × 100

Example:

Premium: $2.10 (bid price)
Strike: $410
Days: 30

$$ \text{ROI} = \frac{2.10}{410} \times \frac{365}{30} \times 100 = 0.51% \times 12.17 = 6.2% \text{ annualized} $$

Is this good? Yes. 6%+ annualized on a 30-day put is solid. If returns drop below 2% annualized, the premium isn't worth the capital lock-up.

Step 5: Place the Order

Right-Click on the Put

In the options chain, right-click on the row where the $410 strike is located.

A menu appears:

Trade
Buy
Sell
Sell Short

Click "Sell" (you're selling the put).

The Order Ticket Opens

A window appears with preset fields:

Action:           SELL
Quantity:         1 contract (= 100 shares)
Order Type:       LIMIT (safer than MARKET)
Limit Price:      $2.10 (or what you want to receive)
Time in Force:    DAY (or GTC = Good Till Canceled)

Adjust the Order Details

Action: Already set to SELL ✓

Quantity: "1" means 1 contract = 100 shares ✓

Order Type:

LIMIT (recommended): Specify the minimum premium you'll accept. Example: you want $2.10/share minimum. You'll wait for that price.
MARKET: Sell immediately at whatever the market offers (could be $2.05 if bid drops). Riskier.

For your first trade, use LIMIT.

Limit Price:

Set it to the bid price or slightly higher (e.g., bid is $2.10, set limit to $2.12)
The limit price is what you'll receive per share
Don't set it too high or your order won't fill

Time in Force:

DAY: Order cancels at end of trading day if not filled
GTC (Good Till Cancelled): Order stays active until filled or you cancel

For first trade, use DAY. You want quick feedback.

Example Completed Order

SELL to open 1 contract MSFT NOV 21 2025 410 Put
Limit Price: $2.10
Time in Force: DAY
Commission: ~$1.65 (IB charges ~$1.65 per options contract)
Net Premium if Filled: $2.10 - $0.017 = ~$2.08/share
Total if Filled: $208 on 1 contract

Step 6: Submit the Order

Click "Transmit" or "Send Order" (button text varies by platform).

A confirmation appears:

Order Confirmed
Order ID: 12345678
Status: SUBMITTED

Your order is now in the market. You're waiting for a buyer (someone else wanting to buy the put from you).

Step 7: Monitor the Order

Watch for Fills

Your order is now "working" in the market. The options market is usually faster to fill than stocks—often fills within seconds.

Check your order status:

In TWS, open "Monitor" or "Orders" tab
Look for your order (Action: SELL, Qty: 1, Strike: 410)
Status will show:
- Submitted: Order received, awaiting fill
- Filled: Congrats! You've successfully sold the put
- Partially Filled: Half your order executed
- Cancelled: Order expired (didn't get filled during the day)

If not filled by market close:

Your DAY order expires
You can resubmit at the same price tomorrow
Or adjust the limit price slightly lower (more attractive to buyers)

Example: Your Order Gets Filled

Order ID: 12345678
Action: SELL to open
Contract: MSFT NOV 21 2025 410 Put
Quantity: 1 (100 shares)
Fill Price: $2.10
Commission: -$1.65
Net Credit: $208.35
Status: FILLED
Timestamp: Oct 21, 2025 10:45 AM

Congratulations. You've successfully sold a cash-secured put. You're now obligated to buy 100 shares of MSFT at $410 if the put is assigned.

Step 8: Confirm Your Position

After fill, check your account to confirm the position is registered.

In TWS:

Go to "Portfolio" or "Positions" tab
Look for a section called "Short Options" or "Selling"
You should see:

MSFT NOV 21 2025 410 Put (Short)
Quantity: -1 contract
Entry Price: $2.10
Current Price: (market value)
P&L: (current unrealized gain/loss)

Also confirm cash reserve:

Your $10,000 cash is now "reserved" (you can't deploy it elsewhere). IB shows this as "Buying Power Reduction" in your Account Summary.

Step 9: Monitor Until Expiration

Your put is now active. Here's what happens each day:

If MSFT stays above $410:

Your put stays out-of-the-money
Premium value decays daily (good for you)
On Nov 21, put expires worthless
You keep the $208 premium as profit ✓

If MSFT drops below $410:

Your put goes in-the-money
Premium value increases (bad for you)
You have options:
- Let it expire and take assignment (own 100 shares)
- Buy it back early (close the position, free up cash)
- Roll it (sell a later put at a lower strike for more premium)

For your first trade: let it expire. Don't close early or get fancy.

Step 10: Assignment Day (If It Happens)

Expiration date arrives. If MSFT is below $410, you're assigned.

What happens automatically:

Your broker executes the assignment
100 shares of MSFT are deposited to your account (at $410 strike)
$41,000 cash is withdrawn from your account
Your short put position closes

You now own 100 shares of MSFT.

Check your account:

Positions (Stocks)
MSFT: 100 shares @ $410 cost basis
(Your cost basis is actually $410 - $2.10 = $407.90 after the premium)

Next step: You have options:

Hold the shares (you bought them at your target price!)
Sell covered calls against them (generate more income)
Exit immediately (take your assignment cost basis as the loss if down)

Common Mistakes to Avoid

Mistake 1: Selling Too Deep in the Money (High Strike)

Wrong: MSFT at $427, sell $430 put. This is basically guaranteeing assignment.

Right: MSFT at $427, sell $410 put. You get premium and assignment probability is low.

Why it matters: Deep ITM puts almost always get assigned. You're not "selling" anymore, you're "committing to buy." That's OK if you meant to, but dangerous if you didn't.

Mistake 2: Ignoring the Bid-Ask Spread

Wrong: Setting limit price at the midpoint of bid-ask spread. Example: Bid $2.10, Ask $2.40. Set limit at $2.25.

Your order might sit all day without filling because you're underselling compared to what buyers are asking.

Right: Set limit to the bid price ($2.10) or slightly higher ($2.12). Increases chance of fill.

Mistake 3: Selling Puts You're Not Comfortable With

Wrong: Selling a put on a stock you'd hate to own. You just want the premium.

Result: You get assigned. Now you own 100 shares of a stock you dislike. Bad decision made.

Right: Only sell puts at strikes you'd genuinely like to own the stock at.

Mistake 4: Over-Sizing Your Position

Wrong: Selling 5 puts on a stock (500 shares worth) when your account can only handle 200.

Result: Multiple assignments overwhelm your cash reserves. You're scrambling.

Right: Sell only 1-2 puts per stock. Keep dry powder.

Mistake 5: Selling Puts Right Before Earnings

Wrong: Earnings are in 3 days. Stock has high IV. Premium looks fat. You sell.

Earnings come. Stock gaps 10%. Your put moves deep ITM. You get assigned at the worst time.

Right: Avoid earnings dates. Sell puts 2+ weeks after earnings, or 1+ week before.

Tax Considerations

Short-term vs long-term:

Premium from selling puts is always short-term income (ordinary income tax rates)
If you're assigned and hold the stock long-term (1+ year), future gains are long-term
If you're assigned and exit quickly, gains are short-term

Recordkeeping:

Track: date sold, strike, premium received, date expired, assignment status
Use a spreadsheet or broker's tax reports
Interactive Brokers provides downloadable tax data

Progression: From First Trade to System

Month 1: Sell 1 put per stock on 2 stocks. Track everything.

Month 2-3: Sell 1-2 puts per stock on 4-5 stocks. Refine timing.

Month 4+: Sell puts on a recurring basis. Track monthly income. Optimize for best premiums.

By month 6, you'll have sold 15-20 puts. You'll have real data on outcomes, assignments, and returns.

Your First Trade Checklist

Next Steps After Your First Put

Wait for 30 days. Let time decay work.
Monitor weekly. Check if your put is still on track.
If assigned: Note the outcome. Did you like owning the stock?
If not assigned: Collect the premium. Repeat the process.
After 5-10 puts: Review your data. Are you profitable? Comfortable? Ready to scale?

The Bottom Line

Selling cash-secured puts on Interactive Brokers is straightforward once you know the process.

Find a stock you'd buy at a target price
Sell a put at that price
Collect premium
Wait for expiration
Either keep the premium (happy) or own the stock (also happy)

It's that simple. Now it's your turn.

To maximize your CSP returns, read our complete cash-secured puts playbook with DTE-specific strategies. Not sure which stocks to target? Check out our stock screening guide. And to optimize your entry timing, learn about implied volatility and DTE.

Cash-Secured Puts Playbook: DTE Optimization & Assignment Risk - Master DTE-specific CSP strategies
Best Stocks for Selling Cash-Secured Puts: 2025 Screening Guide - Find the best stocks for your CSP trades
Implied Volatility & Days to Expiry: Timing Your Options Entries - Time your entries perfectly

How to Sell Cash-Secured Puts: Interactive Brokers Walkthrough