Column Tax

Cash App Taxes (formerly Credit Karma Tax) is the most genuinely free tax filing service available, covering both federal and state returns at zero cost for virtually all filers — with no income limits, no hidden upgrade prompts, and no premium features locked behind a paywall. Owned by Block (formerly Square), it serves as a financial gateway to Cash App's broader ecosystem of banking, investing, and payments. The filing software handles a comprehensive range of tax situations: W-2 income, 1099 freelance income (Schedule C), investment sales (Schedule D), rental income (Schedule E), itemized deductions, educational credits, retirement contributions, and more. The interface is straightforward and well-paced, walking users through an organized interview with contextual help at each step. Import capabilities cover W-2 PDFs and prior-year returns uploaded as PDFs. One notable limitation is the lack of live CPA or enrolled agent support — users who need professional guidance during filing must seek assistance elsewhere. Multi-state filing is also limited in some edge cases. Despite these gaps, Cash App Taxes covers the vast majority of individual filer scenarios and represents an extraordinary value proposition. For any filer with a straightforward-to-moderately-complex return who is comfortable navigating tax software independently, Cash App Taxes is difficult to beat.

TaxSlayer is a reliable tax filing platform that has served consumers and professional tax preparers since 1965, offering competitive pricing particularly for self-employed filers and military service members. The Classic plan at $22.95 handles all standard tax situations including itemized deductions, investment income, and rental income — covering significantly more than the basic tiers of competitors at a comparable price. The Self-Employed tier at $52.95 is among the most affordable dedicated freelancer packages in the market, including Schedule C guidance, self-employment tax calculation, and home office deduction. Military members receive the Classic tier completely free. TaxSlayer's interface has improved significantly in recent years with a cleaner step-by-step interview, though it remains less visually polished than TurboTax. The Premium plan adds Ask a Tax Pro live chat support with CPAs and enrolled agents. Prior-year data import works reliably from TaxSlayer's own platform and accepts PDFs from competitors. The mobile apps for iOS and Android are capable and support fingerprint login. Occasional navigation quirks and less comprehensive help documentation compared to TurboTax are the main drawbacks. For users with self-employment income, Schedule D investment sales, or active military status seeking quality filing software at a below-market price, TaxSlayer represents outstanding value.

Keeper Tax is purpose-built for freelancers, contractors, and gig economy workers who have business expenses eligible as tax deductions but lack the accounting knowledge to identify and document them effectively. The app connects to bank accounts and credit cards, then uses AI to automatically scan transaction history for potential business deductions — flagging purchases that commonly qualify for Schedule C write-offs across hundreds of occupation categories. Keeper's deduction-finding algorithm is trained on IRS guidelines and covers expenses ranging from home office costs and software subscriptions to business meals, vehicle mileage, and professional development. Each flagged transaction is presented for user confirmation, keeping humans in the loop while doing the heavy lifting of identification. The subscription price covers both year-round deduction tracking and actual tax filing at year-end — users don't pay separately for the return. Keeper also offers quarterly tax estimates to help freelancers avoid underpayment penalties. A CPA review option is available for complex situations. The platform's tax filing covers Schedule C, self-employment tax, retirement contributions (SEP-IRA, Solo 401k), home office deduction, and most common freelancer scenarios. For independent workers who previously left thousands of dollars in deductions on the table, Keeper's automated approach often saves significantly more than the subscription cost.