Analyzing an Interactive Brokers portfolio is spreadsheet hell. You export a CSV, open it in Excel, write formulas to calculate DTE and premium totals, then realize you exported the wrong date range and start over.
What most traders do next is worse: they copy-paste portfolio data into ChatGPT. It feels smart—until the model hallucinates a strike price, misreads a date format, or gives advice based on stale data.
There is a better way. A live data connection that lets you ask your portfolio questions in plain English and get answers backed by real-time IBKR data.
The Problem: IBKR Analysis is a Data Pipeline, Not a Conversation
Interactive Brokers gives you everything. Greeks, P&L, assignment history, flex queries. But the interface assumes you are a quant who enjoys SQL-like filtering and manual reconciliation.
The typical workflow looks like this:
- Log into IBKR Account Management
- Run a Flex Query for open positions
- Download CSV
- Open in Excel or Google Sheets
- Calculate DTE manually (Excel date math is painful)
- Try to remember which positions you rolled last week
- Give up and trade on intuition
Even traders who export regularly rarely do it more than once a week. By Wednesday, your "portfolio view" is already stale.
Why Copy-Paste into ChatGPT Breaks
Copy-pasting into ChatGPT feels like a shortcut. It is actually a reliability trap:
- Hallucination risk: The model might misread "AAPL 180 Call" as "AAPL 190 Call" and give you roll advice on the wrong strike
- Stale data: Your paste is a snapshot. If AAPL moves 3% after you paste, the AI's advice is wrong
- Context loss: The AI cannot see your full trade history, so it does not know you already rolled this position twice
- Privacy exposure: You are pasting financial data into a third-party service with unclear retention policies
The root problem is that ChatGPT has no connection to your actual portfolio. It is analyzing a static text dump, not live positions.
The Better Way: A Live Data Connection
Days to Expiry exposes your portfolio data through a secure API that connects directly to Claude, Cursor, or Windsurf. Instead of copy-pasting, you ask questions and the AI pulls fresh data in real time.
Here is what that looks like in practice:
"Which positions expire this week?"
The AI queries your live portfolio, checks every open position's expiration date, and returns a sorted list with DTE, strike, and moneyness. No manual date math. No CSV exports.
"What's my best roll opportunity right now?"
The AI runs the portfolio's rolling alert engine against your positions. It checks DTE zones, assignment probability, and roll economics. Then it presents the top candidates with projected P&L for each option.
"Find me a covered call on AAPL with 30 DTE and 0.30 delta"
The AI triggers the opportunity scanner with your exact filters, pulls live options chain data with Greeks, and returns the best matches—complete with backtested assignment rates and ROI projections.
"How much premium did I collect last month?"
The AI queries your trade history, filters for closed short options positions in the date range, sums premiums collected, and breaks it down by strategy and underlying. It takes about 2 seconds.
"Should I roll my TSLA put or let assignment happen?"
The AI pulls your TSLA position detail, checks the current mark, analyzes roll options at nearby strikes and expirations, and compares the economics of rolling versus taking assignment. It presents both scenarios with projected outcomes.
How to Set It Up
The setup is simpler than most traders expect. You need two things: a Pro subscription and about 30 seconds.
Step 1: Generate an API key
In Days to Expiry, go to Profile → Connect Your AI. Click "Generate New Key." Copy the full key—you will only see it once.
Step 2: Paste into your AI app
The page gives you a JSON config snippet. Copy it and paste it into your AI app's MCP settings:
- Cursor:
~/.cursor/mcp.json - Claude Desktop:
~/Library/Application Support/Claude/claude_desktop_config.json - Windsurf:
~/.codeium/windsurf/mcp_config.json
Step 3: Start asking questions
Restart your AI app. The connection is live. Ask "Which positions expire this week?" and watch it respond with real data from your portfolio.
What the AI Can Actually Do
The integration exposes 9 portfolio tools to your AI:
| Capability | Example Question |
|---|---|
| Full portfolio view | "Show me my open positions sorted by DTE" |
| Trade history query | "How many assignments did I have in Q1?" |
| Position deep-dive | "What's the roll economics on my AAPL call?" |
| Roll alerts | "Which positions need attention this week?" |
| Opportunity scanning | "Find CSPs under $50 with 30 DTE" |
| Scan status check | "Are my scanner results ready?" |
| Flex query import | "Import my latest IBKR flex query" |
| Strategy finder | "What covered calls match my criteria?" |
| Options chain | "Show me the AAPL chain for June expiry" |
The AI does not make investment recommendations. It is a data interface. You ask, it retrieves and presents. The decisions are still yours.
Security and Privacy
This is the most common concern, and it is valid. Here is how the connection works:
- Scoped API keys: Each key is unique to your account and can be revoked instantly
- Read-only access: The AI can query your portfolio data but cannot execute trades
- No training data: Your portfolio data never feeds into AI model training
- Bearer token auth: Every request is authenticated and encrypted in transit
- No data retention: Days to Expiry does not store AI conversation history
Compare this to copy-pasting into ChatGPT, where your data enters a third-party system with opaque retention and training policies.
Who This Is For
This integration is designed for traders who:
- Manage 10+ open positions and lose track of expiration dates
- Want to scan for opportunities without clicking through 4 screens
- Prefer conversational analysis over spreadsheet pivot tables
- Already use Claude, Cursor, or ChatGPT for research and want the same interface for portfolio management
It is not for traders who enjoy manual reconciliation or who only hold 2-3 positions at a time. The value scales with portfolio complexity.
Try It Without Connecting Your Portfolio
Not ready to generate an API key? You can see the AI interaction model on our demo portfolio. The demo shows example questions and responses using realistic positions—no account required.
If you want to explore the full feature set first, check out our platform features page. The AI analysis layer sits on top of the same portfolio engine that powers the dashboard, scanner, and backtesting tools.
The Bottom Line
Interactive Brokers gives you the data. Days to Expiry organizes it. The AI connection turns it into a conversation.
You do not need to export CSVs, write Excel formulas, or paste screenshots into ChatGPT. You just ask.
Demo Portfolio Overview
Explore positions, trades, income, and analytics with realistic sample data.
Want to track your own portfolio? Import your trades and see analytics like this.
Try FreeReady to connect your AI? Upgrade to Pro and generate your API key in under a minute.
Frequently Asked Questions
Written by Days to Expiry Trading Team
The Days to Expiry trading team brings together experienced options traders and financial analysts dedicated to helping investors generate consistent income through proven options strategies.
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