- Intro: 2026, the First Season Where Tax Filing Moved to AI Assistants
- 1. The 2026 Tax Tech Landscape
- 2. US Consumer Tax - The TurboTax + Intuit Assist Dominance
- 3. H&R Block + AI Tax Assist
- 4. FreeTaxUSA - The Affordable Stalwart Rises
- 5. Cash App Taxes - The All-Free Route
- 6. TaxAct · Jackson Hewitt · TaxSlayer
- 7. IRS Direct File - The Government's Free Direct Filing
- 8. What AI Assistants Actually Do
- 9. US Business and Accountant Tools
- 10. Practice Management
- 11. Sales Tax and VAT Compliance
- 12. Korea - The Evolution of NTS Hometax
- 13. Samjeomsam (3.3 / Jobis & Villains) - The Refund Market Storm
- 14. Toss Tax Service · KakaoBank Tax Refund
- 15. Korea B2B - Smart-A · Wetax · eTax
- 16. Korean AI Tax - Chatbots and Auto-Matching
- 17. Japan - The Invoice System and Electronic Bookkeeping Law
- 18. NTA e-Tax + My Number Portal Integration
- 19. freee Accounting + Tax Filing
- 20. Money Forward Cloud
- 21. Yayoi - Desktop Era Stalwart, Cloud Era Challenger
- 22. TKC · PCA · Daichoku Daijin - Japan's Other Axis
- 23. Real-Time Bookkeeping
- 24. Crypto Tax - Koinly · CoinTracker · Cryptact
- 25. Self-Employed and Gig - QuickBooks Self-Employed · Found · Jjantaek
- 26. AI Risks - Hallucination, Liability, Regulation
- 27. Real-World Filing Workflow Examples
- 28. Wrap-Up
- References
Intro: 2026, the First Season Where Tax Filing Moved to AI Assistants
The 2026 tax filing season marks a clear inflection point. What was just last year a "tried chatting with an AI about taxes" novelty has, this year, moved deep inside the default workflow of consumer tax software like TurboTax and H&R Block. Users no longer ask "what goes in this box" - they ask context-aware questions like "how do I combine these two 1099-NECs with last year's K-1 on my return," and the AI answers in place and fills the corresponding fields on the form.
This is not just a US story. Korea's National Tax Service Hometax has strengthened its chatbot and auto-refund recommendations, while mobile refund apps like Samjeomsam (3.3 / Jobis & Villains), Toss Tax Service, and KakaoBank Tax Refund have become the first entry point for ordinary filers. In Japan, the October 2023 enforcement of the Invoice System (qualified invoice retention method) and the January 2024 mandatory enforcement of the Electronic Bookkeeping Preservation Law have effectively forced everyone toward cloud accounting tools like e-Tax, freee, Money Forward, and Yayoi.
This post covers consumer tax apps, business and accountant tools, government portals, AI features, risks, and controversies across the US, Korea, and Japan markets - all in one place.
1. The 2026 Tax Tech Landscape
Start with the macro view. First, AI Q&A is now pervasive. TurboTax Intuit Assist and H&R Block AI Tax Assist, both pilot-launched in the 2024 season, are by the 2025 and 2026 seasons default features across free and paid tiers. Second, IRS Direct File expansion. The IRS's free direct-filing service began as a 12-state pilot in the 2024 season, expanded to 25 states in 2025, and supports more income types and credits in the 2026 season. Third, deepening AI inside Korea's Hometax. Chatbots, auto-filing recommendations, expected refund notifications - all now flow through the mobile Sontax app. Fourth, Japan's mandatory Invoice and Electronic Bookkeeping enforcement has exploded the cloud accounting market.
These four trends together are rapidly shifting tax from a "specialists-only" activity to a "with an AI assistant by your side" activity. That said, the IRS, Korean Consumer Agency, and Japan's NTA are all watching AI accuracy and liability closely, so users still own the final review and the final responsibility.
2. US Consumer Tax - The TurboTax + Intuit Assist Dominance
The US personal tax software market remains overwhelmingly dominated by TurboTax. Per Intuit's FY2024 report, the ProTax + Consumer segment exceeded $5B in revenue, with TurboTax at its core. It officially launched the "Intuit Assist" GenAI assistant in the 2024 season, and integration deepened by 2026.
- TurboTax Free Edition: For W-2-only filers. Intuit cites about 37% of filers as eligible for free, but side income, student loan interest deductions, etc., quickly bump filers into paid tiers (Deluxe / Premier / Self-Employed).
- TurboTax Deluxe / Premier / Self-Employed: Tiered pricing that climbs every year. For the 2026 season, Self-Employed federal-alone is about $130 and state-alone is about $60 (pre-deadline price hikes are normal).
- TurboTax Live: Real EAs / CPAs review on video. Live Full Service hands off the entire return to a pro - $200 to $600+ depending on complexity.
- Intuit Assist: GenAI assistant. Answers natural-language questions like "compare to last year's 1099" or "should I take the standard mileage or actual expenses for vehicle costs," and auto-fills form fields.
Note that Intuit settled with the FTC in 2022 over an order to more clearly signal free filing eligibility to eligible users, and "Free" labeling guidelines have since tightened.
3. H&R Block + AI Tax Assist
H&R Block launched the industry's first AI Q&A "AI Tax Assist" in the 2024 season - that is, January through April of 2024. It's publicly disclosed as built on Microsoft Azure OpenAI, combined via RAG with H&R Block's six-decade tax content and guides.
- H&R Block Online (DIY): Free through paid (Deluxe / Premium / Self-Employed). AI Tax Assist is unlimited from a certain tier upward.
- H&R Block Tax Pro Review: User does the input, a tax pro reviews at the end.
- H&R Block Tax Pro Go: Full pro service from start to finish.
- Retail locations: 9,000+ offices across the US. Digital plus retail is H&R Block's structural differentiation.
H&R Block's strengths are (1) early AI Q&A launch, (2) the retail handoff for complex cases, and (3) the "Second Look" free past-return review service.
4. FreeTaxUSA - The Affordable Stalwart Rises
FreeTaxUSA, operated by TaxHawk Inc., is a low-cost tax software that's frequently picked as the best value option in the 2026 season too.
- Free federal filing: Federal is free at any complexity. Schedule C self-employment, Schedule E rental, Schedule D capital gains, 1040-NR non-resident (handled separately) - all broadly supported.
- About $15 per state return: Each state return is around $15 - very affordable.
- Deluxe option (~$8): Adds priority support, live chat, audit assist.
- Pro Support (~$40): Tax pro chat support.
The UI lacks TurboTax's polish but is form-driven, intuitive, and fast. User counts grew rapidly across the 2024 and 2025 seasons, making it the most widely recommended "TurboTax alternative" in the US.
5. Cash App Taxes - The All-Free Route
Cash App Taxes is the successor to Credit Karma Tax, which Square (now Block) acquired. It's an unusual case - when Intuit acquired Credit Karma in 2020, only the tax business was carved out to Cash App for antitrust reasons.
- Free federal and state filing: Truly free, with no ads or upsells.
- Mobile-first (built into Cash App): Natural entry for Cash App users.
- Limited coverage: No multi-state filing, foreign tax credit, or non-resident (1040-NR) support.
- W-2 and 1099 imports auto-populate, so simple returns finish in 5-10 minutes.
Because the price is zero, UI depth and case coverage trail TurboTax and FreeTaxUSA. For W-2 and 1099-INT only filers, it's the fastest path.
6. TaxAct · Jackson Hewitt · TaxSlayer
Beyond the top four, several other meaningful US consumer tools exist.
- TaxAct: A veteran since 1998. Prices below TurboTax but above FreeTaxUSA. Marketing centers on a "$100K Accuracy Guarantee."
- Jackson Hewitt: The #2 US retail chain. Walmart in-store kiosks are signature. Online too, but retail is the core.
- TaxSlayer: Known for free Military Edition. Mid-tier pricing.
- Liberty Tax: US and Canadian retail chain. Online too.
Choosing tax software depends on (1) return complexity, (2) DIY vs. pro-reviewed preference, (3) price sensitivity, and (4) mobile vs. desktop preference.
7. IRS Direct File - The Government's Free Direct Filing
The US IRS piloted "Direct File," a free direct filing system, in 12 states in the 2024 season, and expanded to 25 states in 2025.
- 2024 pilot: 12 states, simple W-2 plus standard deduction. About 140,000 actually used it.
- 2025 expansion: 25 states, added EITC, CTC, student loan interest, some 1099s. About 3 million eligible.
- 2026 season: Adds more states and forms. Subject to volatility under the Trump 2.0 administration's policy shifts.
- API integrations: Some states (California, New York, Illinois, etc.) smoothly hand off into state filings.
IRS Direct File is a lever against commercial tax software vendors. The two key variables remain coverage scope and political durability.
8. What AI Assistants Actually Do
In hands-on use of TurboTax, H&R Block, and FreeTaxUSA AI Q&A, similar limits emerge.
- What they do well: Explain form semantics, identify simple deduction and credit eligibility, answer general tax law questions, auto-fill form items.
- What they struggle with: Multi-state, non-resident, complex K-1, foreign tax credit, and other compound scenarios. AI often falls back to "consult a pro" for these cases.
- Factual consistency: Different answers to the same question at different times. So vendors prominently disclaim that "AI responses are for reference; the user is responsible for the final return."
The 2024 Washington Post and Wall Street Journal reporting flagged multiple hallucination cases in TurboTax and H&R Block AI, and both vendors have since strengthened answer accuracy and source citation.
9. US Business and Accountant Tools
The enterprise and accountant market has different dominant players than the consumer side.
- Drake Tax: The standard for small-to-midsize accountants and tax preparers. Reasonable pricing, desktop-based.
- UltraTax CS (Thomson Reuters): The mid-to-large firm standard. Integrated with the CS suite (Practice CS, Workpapers CS).
- Lacerte (Intuit): TurboTax's cousin. Accountant edition.
- ProSeries (Intuit): For small accountants. Cheaper than Lacerte.
- CCH Axcess Tax (Wolters Kluwer): Cloud-based firm-grade solution.
- ProConnect Tax Online (Intuit): Lacerte's cloud version.
Accountant tools center on (1) multi-client management, (2) e-File automation, (3) workpaper and review workflows, and (4) audit risk scoring.
10. Practice Management
During tax season, you also need tools to manage client data, documents, schedules, and billing.
- TaxDome: Integrated practice management. Client portal, e-signature, billing, workflows.
- Canopy: Client management, tax resolution, time tracking.
- Karbon: A firm collaboration platform. UK origins.
- Jetpack Workflow and Pixie: Workflow for small firms.
These shape firm operations more than the tax software itself. Since 2024, AI auto-categorization and auto-summary features have become common.
11. Sales Tax and VAT Compliance
US sales tax and global VAT compliance live in their own world. After the 2018 South Dakota v. Wayfair Supreme Court ruling, US sellers must track economic nexus thresholds in all 50 states.
- Avalara: Market leader. 14,000+ rate database, integrations with e-commerce, ERP, and accounting software. Acquired by Vista in 2022 (private).
- Vertex: Enterprise (large multinational) leader. Integrates with SAP and Oracle ERP.
- Sovos: Global VAT and e-invoicing. Strong in Latin America.
- TaxJar (Stripe acquisition): SMB and e-commerce sellers. Natural pairing with Stripe payments data.
- Anrok: Global SaaS sales tax specialist. Integrates with Stripe, Recurly, etc.
SaaS and digital-goods sellers expanding globally meet sales tax and VAT compliance as their first painful headwall, and the space is increasingly automated.
12. Korea - The Evolution of NTS Hometax
The starting point for Korean tax is always the National Tax Service's Hometax. As of 2026, Hometax has evolved into four channels - PC web, mobile Sontax, chatbot, and API - covering almost all filing, payment, and refund flows.
- Comprehensive Income Tax Filing (May): Filed in May if business income, real estate, interest, dividend, or other income are present alongside or instead of wage income.
- Year-End Settlement (Jan-Feb): For salaried workers' wage income tax reconciliation. Employers do it, but Hometax's data-lookup and simplified service are the core infrastructure.
- VAT Filing (January and July): Quarterly for general businesses (simplified taxpayers file annually).
- Withholding Tax (semi-annual or monthly): For businesses on income they paid out.
- Cash Receipts and Tax Invoices: Issue, lookup, download.
The Hometax chatbot was upgraded to LLM-based in 2025, now able to answer natural-language questions like "I'm a freelancer - how do I file comprehensive income tax." Core filing steps still require the user to type and submit, however.
13. Samjeomsam (3.3 / Jobis & Villains) - The Refund Market Storm
The undisputed force that changed Korea's refund landscape is Jobis & Villains' "Samjeomsam." The 3.3% in the name comes from the freelancer business-income withholding rate, and its core promise is "we automatically find the refund freelancers missed."
- User count: Over 19 million cumulative signups by year-end 2024. Most of Korea's economically active population has tried it at least once.
- Fee: About 10-15% of the refund (tiered by amount). Caps and free cases change frequently.
- Consumer protection controversy (2023-2024): Conflict with the Korean Tax Accountants Association and the Korean CPA Association over the scope of "tax representation." Constitutional Court and administrative litigation has run for years over the tax accountant law and unlicensed tax representation prohibitions. As of 2024, some actions (active tax advice) are restricted; simple data organization and refund filing are permitted.
- AI features: Refund estimation, deduction auto-matching, business registration guidance, chatbot.
Samjeomsam's arrival created a new category in Korea - "B2C mobile-first refund." Toss and KakaoBank followed into the same category afterward.
14. Toss Tax Service · KakaoBank Tax Refund
A major 2023-2024 event was banks and fintechs entering the tax refund space in earnest.
- Toss Tax Service (Viva Republica / Toss): Refund filing for comprehensive income tax inside the Toss app. From estimated-refund lookup to filing to deposit, all in mobile. Fee is refund-based.
- KakaoBank Tax Refund: Similar model. Strength is the link to KakaoBank deposit, transfer, and autopay data.
- K Bank and Toss Bank refunds: Own refund channels.
- Tax Refund apps: Many smaller apps entered with similar concepts.
Bank and fintech entry intensified price and UX competition; Samjeomsam cut some fees. But the refund itself is processed in the NTS system regardless of app, so outcomes (refund amount) are identical, and the difference is in fees, UX, and auto-matching accuracy.
15. Korea B2B - Smart-A · Wetax · eTax
If consumer refunds are the B2C market, businesses (sole proprietors, corporations) play a different game.
- Smart-A Plus (Sumusarang) (Douzone Bizon): The standard for Korean accounting and tax firms. Books, VAT, comprehensive income tax, corporate tax, four social insurances - all integrated.
- Wetax: The Ministry of Interior and Safety's local tax (auto tax, residence tax, property tax, acquisition tax) portal.
- eTax: Seoul Metropolitan Government's local tax portal.
- TaxOne: Tax processing SW for tax accountants and accounting firms.
- EasyShop: Tax modules inside SMB ERPs like Younglimwon and Douzone.
- Dooray Accounting Integration: NHN's collaboration suite with tax-accounting connectors.
- Samsung SDS and LG CNS Tax Solutions: For chaebol internal use.
Smart-A Plus is the de facto standard for Korean tax-accounting firms, with data flowing on top through Wetax, eTax, and Hometax.
16. Korean AI Tax - Chatbots and Auto-Matching
In 2026, the AI features in Korean tax tools mostly live in these areas.
- Chatbots (Hometax, Samjeomsam, Toss): Natural language Q&A.
- Deduction auto-matching: Medical, education, donation, credit card, cash receipt, and medical data are auto-fetched and matched to deduction items.
- Expected refund estimation: Predicts refund based on user income and spending.
- Auto-classification of business income: Auto-organizes withholding receipts for business income (Korea's equivalent to 1099 forms).
- Tax schedule reminders: Quarterly VAT, May comprehensive income tax, January year-end settlement, etc.
But AI automation has the same limits as in the US. Complex cases (multinational, virtual assets, real estate capital gains, inheritance) practically require working with a tax accountant.
17. Japan - The Invoice System and Electronic Bookkeeping Law
To understand Japan's 2026 tax landscape, two major events must be known.
- Invoice System (qualified invoice retention method) - Effective October 1, 2023. To claim input VAT credit, you need an invoice from a registered qualified invoice issuer. Before, tax-exempt businesses were largely fine in transactions, but post-Invoice System, tax-exempt businesses are increasingly being asked to register by trading partners.
- Electronic Bookkeeping Preservation Law - Mandatory from January 1, 2024. Electronic transaction data (email attachments, internet downloads, etc.) must be retained electronically, not on paper. Violations can affect blue-form filer eligibility.
Together they drove all Japanese businesses (particularly freelancers and sole proprietors) toward cloud accounting tools by effective force, which directly explains the explosive growth of freee, Money Forward, and Yayoi.
18. NTA e-Tax + My Number Portal Integration
The Japan National Tax Agency's official channel is e-Tax (the National Tax Electronic Filing and Payment System).
- e-Tax: Filing for income tax, consumption tax, corporate tax, inheritance tax, and almost all national taxes electronically. PC web and smartphone supported.
- My Number card + My Number Portal integration: Medical expenses, iDeCo, insurance premiums, etc. auto-flow into e-Tax as deduction data. Effective since 2024. Conceptually similar to Korea's Hometax simplified service.
- Tax Return Creation Corner (Kakutei Shinkokusho Sakuseishon Coner): Free NTA tool. Following the prompts produces a PDF or electronic filing data.
- Digital Agency leadership: The Digital Agency, established in 2021, is pushing overall e-government integration. Tax is a major part.
The Japanese government is moving fast through My Number plus My Number Portal plus e-Tax integration to target user experience comparable to Korean Hometax.
19. freee Accounting + Tax Filing
freee is the standout in Japanese cloud accounting. Listed on Tokyo Stock Exchange Growth Market (2019 IPO).
- freee Accounting: The flagship cloud accounting product. Receipt OCR, bank and card auto-feeds, automated bookkeeping.
- freee Invoice: Invoice System response. Issue, store, and process qualified invoices.
- freee HR (Jinjirou-mu): Payroll, social insurance, year-end adjustment.
- freee Tax Filing (Kakutei Shinkoku): For sole proprietors, all the way through blue-form filing. e-Tax integration.
- AI features: Receipt OCR, automatic account categorization, chatbot, qualified invoice registration number auto-validation.
freee's strengths are (1) UX friendly to non-accountants (owner handles books directly), (2) early shipping of Invoice and Electronic Bookkeeping compliance, and (3) mobile-first design.
20. Money Forward Cloud
freee's largest competitor is Money Forward. Born as a household finance app, it expanded into B2B cloud.
- Money Forward Cloud Accounting: B2B cloud accounting. A strong freee rival.
- Money Forward Cloud Invoice: Invoice issuance and storage.
- Money Forward Cloud Payroll: Payslips, social insurance.
- Money Forward Cloud Tax Filing: For sole proprietors.
- Money Forward ME: B2C household finance. The original product.
The freee vs. Money Forward distinction is often framed as (1) freee is more familiar to non-accountants, Money Forward to bookkeeping-literate users and tax accountants; and (2) Money Forward has richer migration options from legacy accounting SW.
21. Yayoi - Desktop Era Stalwart, Cloud Era Challenger
Yayoi is a longtime giant of Japanese accounting SW. It's been shipping desktop accounting SW since the 1980s; in the cloud era, it ceded share to freee and Money Forward but remains a core player.
- Yayoi Accounting (Yayoi Kaikei): The desktop standard. Used by many SMBs and accountants.
- Yayoi Blue-Form Filing (Yayoi no Aoiro Shinkoku): For sole-proprietor blue-form filing. 30+ years in market.
- Yayoi Cloud Series: A line that brings desktop assets to the cloud. Cloud-native posture trails freee and Money Forward.
- Yayoi Pay and Invoice Compliance: Invoice and Electronic Bookkeeping features added in 2023-2024.
Yayoi's strengths are (1) desktop compatibility and low migration friction, (2) accountant and tax-pro familiarity, and (3) reasonable pricing versus freee and Money Forward.
22. TKC · PCA · Daichoku Daijin - Japan's Other Axis
Beyond freee, Money Forward, and Yayoi, the mid-to-large Japanese accounting market has veteran heavyweights.
- TKC Accounting (TKC National Federation / TKC System): The standard at accountant and tax-pro offices. Cloud (FX2, etc.) blended with accountant network reach.
- PCA Accounting (PCA Corporation): Accounting, payroll, and sales management SW for mid-market. Both desktop and cloud.
- Daichoku Daijin (Ohkura Daijin / Ohyou System): Mid-market accounting and payroll SW. Package-based.
- MJS (Miroku Information Service): For accounting firms and mid-market. ACELINK product line.
- SAP · Oracle · Workday: Large enterprise and multinational market.
Accountant offices use TKC and MJS; mid-market uses PCA and Daichoku Daijin; sole proprietors and small businesses use freee, Money Forward, and Yayoi.
23. Real-Time Bookkeeping
Tax is ultimately the downstream of bookkeeping data. So the 2026 core trend is the shift from "batch bookkeeping at month-end" to "auto-categorization per transaction."
- QuickBooks Online + AI (Intuit): The global SMB accounting standard. AI auto-categorization, receipt OCR, chatbot.
- Xero + AI: A New Zealand-born global SMB accounting platform. Strong in UK, AU, NZ. Expanding in the US.
- FreshBooks: Stalwart for freelancers and sole proprietors. Integrates invoicing, billing, time tracking.
- Sage: UK and European SMB and mid-market. Over 50 years old. Shifting to cloud (Sage Intacct).
- Wave: Free accounting SW. Acquired by H&R Block in 2019.
QuickBooks Online is the de facto US SMB standard, with natural data integration to TurboTax and Lacerte.
24. Crypto Tax - Koinly · CoinTracker · Cryptact
Crypto (virtual asset) tax is an area general tax software handles poorly, so specialty tools have grown. The US, Korea, and Japan all require reporting on virtual asset trades as gain or income.
- Koinly: The global standard. Supports 800+ exchanges and 100+ blockchains. Auto-generates tax forms for 30+ countries (US 8949, UK SA108, Australia, etc.).
- TokenTax: Strong in the US market. Excellent at complex DeFi and NFT cases.
- CoinTracker: Official TurboTax partner (Intuit investment). Direct import into TurboTax.
- CoinTracking: A veteran. Multi-currency, multi-accounting-method (FIFO, LIFO, HIFO, etc.) support.
- Bithumb Tax Reports (Korea): Korean exchanges like Bithumb provide native transfer data. In preparation for Korean virtual asset capital gains tax (scheduled for 2027 or possibly further delayed).
- Cryptact (Japan): Mercari Group's virtual asset tax SW. Integrates with major Japanese exchanges like bitFlyer and Coincheck. Outputs Japan NTA filing forms.
The hard parts of crypto tax are (1) consolidating data from many exchanges and wallets, (2) valuing DeFi, NFTs, and staking, and (3) different country-level classifications (income vs. capital gain).
25. Self-Employed and Gig - QuickBooks Self-Employed · Found · Jjantaek
Platform work (gig) has driven rapid growth in tools tailored to self-employed and one-person businesses.
- QuickBooks Self-Employed (Intuit): Auto mileage tracking, receipt OCR, quarterly estimated tax computation.
- Found: Banking + bookkeeping + tax integrated for one-person businesses. Auto-reserve for estimated tax.
- Lili: Similar model. Digital bank plus bookkeeping for sole proprietors.
- Wave (H&R Block): Free bookkeeping + paid payments.
- Jjantaek: Korean refund and tax tool for gig workers, delivery riders, and couriers. Mobile-first.
Gig worker tax headaches are (1) consolidating income from many platforms, (2) separating business expenses (mileage, communications, equipment, etc.), and (3) automating quarterly estimated tax payments.
26. AI Risks - Hallucination, Liability, Regulation
Finally, the risks of AI tax tools.
- IRS warning (2024): The IRS explicitly cautioned against trusting AI chatbot tax advice. Filing responsibility still sits with the taxpayer.
- TurboTax and H&R Block AI hallucination cases (2024): Multiple cases reported by Washington Post and WSJ. Both vendors announced response accuracy improvements.
- Samjeomsam controversy (Korea): Dispute with the Korean Tax Accountants Association over qualifications, and some accuracy concerns on refund estimation.
- Data breach risk: Tax SW handles the most sensitive data (SSN, RRN, bank accounts). A breach has outsized impact.
- Rising AI dependence: If users trust AI answers as-is, they risk filing without understanding their own return.
The reasonable 2026 usage pattern is "AI as copilot, final review by you or a pro."
27. Real-World Filing Workflow Examples
To close, here are typical filing workflows in three countries, in time order.
- US (W-2 worker + 1099-NEC side gig): Import W-2 into TurboTax Self-Employed or FreeTaxUSA → enter 1099-NEC → input Schedule C expenses → compute Schedule SE self-employment tax → file state return → e-File. Use AI Q&A for ambiguous items. Save the return PDF and IRS receipt.
- Korea (salaried + side business income): Year-end settlement in Jan-Feb (employer) → May comprehensive income tax filing (Hometax or Samjeomsam or Toss). Auto-fetch side-business withholding (3.3%) data from Hometax → enter additional deductions and expenses → refund or extra payment.
- Japan (sole proprietor, blue-form filing): Day-to-day bookkeeping in freee, Money Forward, or Yayoi from January → file by March 15 via e-Tax → auto-fetch medical and iDeCo from My Number Portal → apply 650,000 yen blue-form special deduction → consumption tax filing (if applicable).
28. Wrap-Up
The 2026 tax filing season is rapidly moving toward a "season with an AI by your side." In the US, TurboTax, H&R Block, IRS Direct File, and FreeTaxUSA; in Korea, Hometax, Samjeomsam, and Toss; in Japan, e-Tax, freee, Money Forward, and Yayoi - each presents its own value proposition in its slot. Complex cases (crypto, global SaaS, multinational) still need a professional, but the path of "one person filing in one season" is getting shorter and smarter.
In a future post I'll go deeper on specific scenarios like Korea's virtual asset capital gains tax, Korean global SaaS revenue against US sales tax, and the Japan Invoice System's impact on tax-exempt businesses.
References
- TurboTax: https://turbotax.intuit.com/
- Intuit Assist announcement (Intuit blog): https://www.intuit.com/blog/innovative-thinking/intuit-assist-generative-ai-financial-platform/
- H&R Block AI Tax Assist announcement (2023): https://newsroom.hrblock.com/h-and-r-block-introduces-ai-tax-assist/
- FreeTaxUSA: https://www.freetaxusa.com/
- Cash App Taxes: https://cash.app/taxes
- TaxAct: https://www.taxact.com/
- TaxSlayer: https://www.taxslayer.com/
- IRS Direct File: https://www.irs.gov/about-irs/strategic-plan/irs-direct-file-pilot
- Drake Tax: https://www.drakesoftware.com/
- Thomson Reuters UltraTax CS: https://tax.thomsonreuters.com/us/en/cs-professional-suite/ultratax-cs
- TaxDome: https://taxdome.com/
- Avalara: https://www.avalara.com/
- Sovos: https://sovos.com/
- Anrok: https://www.anrok.com/
- Korea NTS Hometax: https://www.hometax.go.kr/
- Samjeomsam (Jobis & Villains): https://www.3o3.co.kr/
- Toss Tax Service: https://toss.im/
- Wetax: https://www.wetax.go.kr/
- Douzone Smart-A: https://www.duzon.com/
- Japan NTA e-Tax: https://www.e-tax.nta.go.jp/
- Japan NTA Invoice System guide: https://www.nta.go.jp/taxes/shiraberu/zeimokubetsu/shohi/keigenzeiritsu/invoice.htm
- freee: https://www.freee.co.jp/
- Money Forward Cloud: https://biz.moneyforward.com/
- Yayoi: https://www.yayoi-kk.co.jp/
- TKC: https://www.tkc.jp/
- Koinly: https://koinly.io/
- CoinTracker: https://www.cointracker.io/
- Cryptact (Japan): https://www.cryptact.com/
- IRS news on AI advisory caution: https://www.irs.gov/newsroom