User reports using Claude Cowork for tax preparation with complex self-employment returns

Using Claude Cowork for tax preparation

A Reddit user reported using Claude Cowork to handle their tax filing, specifically mentioning they have a complex self-employment situation. The user emphasized they have personal experience with tax filing and tax laws, and warned others not to attempt this unless they know what they're doing.

Key details from the experience

The user provided Claude Cowork with their 1099s and profit/loss statement from their business. According to the report:

• Claude Cowork filled out the forms "perfectly in minutes" after asking a few questions
• The user typically spends "a couple hours each year" cross-referencing different forms, double-checking math, and ensuring everything lines up
• For straight W2 situations, the user suggested this approach "seems like a no-brainer"
• The tool also worked well for "more complex returns as long as you know your numbers"

Privacy considerations

The user took specific privacy measures:

• Turned off data sharing in privacy settings
• Left out their SSN on all forms
• After these steps, they considered the privacy risk "just about the same as using any other digital tax filing tool"

The user suggested this could serve as a "solid free alternative to TurboTax if you'd rather not pay for software."