TaxSlayer

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.

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.

April is an infrastructure-layer tax company that embeds AI-powered tax filing capabilities directly into third-party financial apps via API. Rather than a standalone consumer app, April partners with banks, fintech platforms, and financial institutions to offer seamless in-app tax filing for their customers. The April engine proactively identifies tax optimization opportunities throughout the year — not just at filing time — analyzing financial data to surface deductions, withholding adjustments, and planning strategies in real time. For end users, this means encountering April's tax tools within apps they already use: a bank might integrate April to offer tax filing alongside checking accounts, or a gig economy platform might use April to help workers optimize quarterly estimated taxes. The conversational AI guides users through filing with dynamic questions that adapt based on their financial situation. April's standout capability is its continuous tax intelligence layer — rather than treating taxes as an annual event, the platform provides year-round guidance on how financial decisions affect tax outcomes. From a consumer perspective, access to April depends entirely on whether their existing financial apps have integrated it. The technology is well-regarded in the fintech ecosystem as a genuine innovation in embedded financial services rather than a simple white-label tax solution.