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ChatGPT prompts for cash-secured puts (and how to catch a wrong answer)

Give the AI your put's numbers and ask it to check them, step by step. Here are 8 prompts to copy, and a worked case where a chatbot got the max loss badly wrong.

Options guide · 10-minute read · Updated 2026-10-28

How these prompts work

Each prompt hands the AI numbers you took from your broker, then asks it to check, explain or list. None ask it to choose a stock. That's a guess with confidence, not research.

A cash-secured put, in one line: you sell a Put option and collect a premium now. In return you agree to buy 100 shares at the Strike price if the buyer wants to sell. Your broker sets the cash aside to pay for them.

Fill in the square brackets. These work in any chat assistant. They're one part of using AI for options trading, where you decide and the AI checks.

The 8 prompts

1. Would I own it at this price?

I'm thinking of selling a put on [stock] at strike $[strike]. Ask me 5 questions, one at a time, to test whether I'd truly be happy owning 100 shares at that price for months. Don't give me any opinion on the stock itself.

This is the question that matters most with puts. If you wouldn't buy the shares today at the strike, don't sell the put.

2. Check the cash, break-even and max loss

Cash-secured put. Strike $[strike]. Premium $[premium] per share. One contract = 100 shares. Show every step: premium collected in dollars, cash set aside, break-even price, max gain, and max loss if the stock goes to zero. Use only my numbers. If anything is missing, ask.

3. Say the trade back to me

I plan to sell one put on [stock], strike $[strike], expiry [date], for $[premium] per share. In 4 plain sentences, tell me what I get, what I promise, and what happens if the stock ends below the strike.

4. Outcome table

Same put as above. Make a table of my total result at expiry with the stock at: [5 prices, including one far below the strike]. Show the share result and the premium as separate columns, then the total. Use minus signs for losses.

5. Does it fit my account?

My account holds $[cash]. My rule is no single position bigger than [x]% of the account. This put sets aside $[strike × 100]. Does it fit my rule? If I'm assigned and the stock falls another 20%, what is the loss in dollars, and what share of my account is that?

6. Check the dates I found

My put expires [date]. I looked up: next earnings [date], ex-dividend [date]. Do either fall before expiry? Explain how an earnings report inside the trade changes the risk for a put seller.

Look the dates up on the company's investor page or your broker. See checking the earnings date before selling.

7. Plan what I'll do if assigned

If this put is assigned, I'll own 100 shares at $[strike]. Help me write a plan in advance: when I'd sell a covered call, at what strike relative to my cost, and the price where I'd sell the shares instead. Ask me questions until each step is a clear rule.

8. Test it against my rules

My put-selling rules: [paste them]. My trade: [paste it]. Go through each rule and say pass, fail or unclear. Don't soften a fail.

A worked case: the AI's max loss was wrong (an illustration, not a trade idea)

A made-up stock, XYZ, trades at $50. You'd own it at $45. Your broker's chain shows the 30-day $45 put with a bid of $1.00.

You run prompt 2. Here is a hypothetical answer, showing a slip chat assistants can make:

Three of those four numbers are right. The last one is off by a factor of ten. The real max loss is $4,500 − $100 = $4,400. The AI mixed up per-share and per-contract math somewhere along the way.

Here is how the two answers compare with the stock lower at expiry:

Now follow the trade. A bad news day drops XYZ to $38 before expiry, and it closes there. You're assigned. You now own 100 shares at $45 that are worth $38.

• Shares: ($38 − $45) × 100 = −$700
• Premium kept: +$100
• Total: −$600, and still open if you keep the shares.

A trader who believed "max loss $440" would think this was already past the worst case. It isn't close. Below $38 the loss keeps growing by $100 for every $1 the stock falls.

How to catch a wrong number

The fix takes one minute.

1. Do the four lines yourself first. Cash = strike × 100. Break-even = strike − premium. Max gain = premium × 100. Max loss = cash − premium collected.
2. Sanity-check the size. The max loss on a put is the cash set aside minus the premium, so it's usually close to the full cash amount. If the AI's number is far smaller, it's wrong.
3. Ask it to show the steps. "Show every step" makes slips visible. Here it would have shown the $440 coming from a wrong multiplier.
4. Run it in a tool. The cash-secured put calculator does the arithmetic the same way every time.
5. When they disagree, trust the tool, then find the AI's mistake. Ask it, "Recheck the max loss. Is it per share or per contract?"

The same per-share and per-contract slip shows up with the Greeks too. See can ChatGPT calculate option Greeks?

What never to ask

• "Which stock should I sell puts on?" It's a guess with a confident voice.
• "What's the premium on this put today?" It may not see live prices.
• "Will this put expire worthless?" Nobody knows. Delta on your chain is a rough market estimate.
• "How many puts can I sell?" That's your size rule. Start with how much to risk per trade.

Selling puts is the first step of the wheel strategy. The next step, if you're assigned, is the covered call. Its pack is here: ChatGPT prompts for covered calls.

In Canada, cash-secured puts in a TFSA or RRSP depend on the broker, and options permissions differ from broker to broker. Check yours before you plan around them.

Questions