One Prompt Replaced a $700/Year Tax Service for Day Traders

Jan 19, 2026
Source

The Challenge

If you're a day trader, you know the pain of matching up thousands of trades every year and making sure everything is accounted for correctly for the IRS.

Tax reconciliation for active traders involves:

  • Matching buy and sell orders across multiple platforms
  • Calculating cost basis for each position
  • Tracking wash sales and adjustments
  • Generating accurate reports for tax filing

The Traditional Solution

Previously, this task required paying approximately $700/year for professional tax reconciliation services. These services manually process trade data, match transactions, and prepare IRS-compliant reports.

The Claude Cowork Solution

With Claude Cowork, all it took was one prompt.

Claude Cowork was able to:

  1. Import and parse trade history from multiple sources
  2. Automatically match corresponding buy/sell transactions
  3. Calculate accurate cost basis and gains/losses
  4. Generate IRS-ready reports

The Result

  • Time saved: Hours of manual work reduced to minutes
  • Cost saved: $700/year in professional services
  • Accuracy: AI-powered matching with human verification

Why This Works

Claude Cowork excels at this type of task because it can:

  • Understand context: It recognizes the patterns in trade data without extensive setup
  • Handle complexity: Thousands of transactions are processed systematically
  • Maintain accuracy: Cross-references data to ensure nothing is missed
  • Adapt to formats: Works with various export formats from different brokerages

Source: Original post on X

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