In 2026, AI tax assistants fall into three categories: DIY filing software with an AI chat assistant (TurboTax, H&R Block), tools where AI does real work with a human CPA signing off (FlyFin, Keeper), and professional research tools (TaxGPT, Blue J Tax, Bizora, Filed). H&R Block was named Best Overall Tax Service for 2026 and Best Use of AI by CNET. Its AI Tax Assist, launched in 2023, has grown 152%, handling 6.45 million messages with responses delivered in an average of 2.2 seconds. When the AI cannot answer confidently, users escalate to a live tax professional. New for the 2026 tax season, H&R Block introduced Sidekick, an AI assistant for tax professionals providing expert-verified answers in 2 to 3 seconds. In testing, H&R Block’s AI answered specific deduction questions accurately within 3 seconds but was less aggressive about proactively surfacing deductions than TurboTax. Pricing: Free (simple returns), Deluxe $35, Premium $65, Self-Employed ~$85, all including AI Tax Assist. TurboTax, serving over 100 million filers, uses Intuit Assist to guide a structured interview, scanning answers for deduction opportunities and flagging questions users might not think to ask. Its strength is proactive deduction discovery.