Keeper Tax vs AlphaTax vs FlyFin: Best AI Tax Software for Freelancers 2026

Introduction

If you're a freelancer searching for the right tax software, you've probably come across Keeper Tax, FlyFin, and AlphaTax—three AI-powered platforms that promise to simplify your taxes. But here's what most people don't realize: Keeper and FlyFin are tax filing services, while AlphaTax is a year-round tax planning and optimization platform.

The difference matters. Filing services focus on getting your taxes done once a year. Planning platforms focus on finding every possible deduction and strategy throughout the year to minimize what you owe in the first place.

In this comprehensive comparison, we'll break down pricing, features, and when each platform makes sense—so you can choose the right solution for your freelance business in 2026.

Quick Comparison Table

Understanding the Core Difference

Keeper Tax & FlyFin: Tax Filing Services

Both Keeper and FlyFin are end-to-end tax filing platforms. Their primary goal is to:

• Track your expenses throughout the year
• Categorize deductions automatically
• Prepare and file your tax return

They're designed for freelancers who want someone else to handle their taxes from start to finish.

AlphaTax: Year-Round Tax Planning Platform

AlphaTax is not a filing service. Instead, it's a tax optimization platform that:

• Finds deductions and strategies filing services often miss
• Provides real-time tax planning and scenario modeling
• Optimizes retirement contributions and entity structure
• Exports everything to your CPA or filing service

AlphaTax users typically work with a CPA (or file separately) because they want strategic tax planning, not just basic filing.

Think of it this way:

• Filing services (Keeper/FlyFin): "Get your taxes filed correctly"
• Planning platform (AlphaTax): "Pay the least amount of taxes legally possible"

Keeper Tax: AI Filing Service for Gig Workers

Overview

Keeper Tax (founded 2016) is an AI-powered tax filing service that pioneered automatic expense categorization. Their signature feature is a text message interface where you can ask tax questions and get instant AI responses. Keeper focuses heavily on mobile-first design and is particularly popular among gig economy workers (Uber, DoorDash, Instacart drivers) who need reliable GPS mileage tracking.

Core Value Proposition: "We find your deductions and file your taxes—all from your phone."

Pricing (Correct as of January 2026)

Standard Plan: $199/year

• Federal & state tax filing included
• AI deduction tracking
• Export your data
• Unlimited CPA advice
• Quarterly tax calculator
• Audit protection
• Max refund guarantee

Premium Plan: $399/year

• Everything in Standard
• 1:1 dedicated accountant
• Video call with CPA
• Quarterly tax support (Form 1040-ES)
• All entities: S-Corp, K-1s, etc.

Business Plan: $1,199/year

• Everything in Premium
• S-Corp tax filing
• Partnership tax filing
• Year-end book review & close

Key Features

• AI Text Message Assistant - Ask tax questions via SMS, get instant AI answers
• Automatic Bank Sync - Plaid integration with 10,000+ banks for automated expense tracking
• GPS Mileage Tracking - Background tracking with automatic business/personal classification
• Receipt Scanning - Photo capture with AI categorization
• Tax Filing Included - CPA-prepared federal and state returns
• Chrome Extension - Automatically tracks online business purchases
• Quarterly Tax Calculator - Basic estimated payment calculator
• Write-Off Library - 100+ deduction explanations

Best For

Gig workers and 1099 contractors who want end-to-end tax filing with minimal effort. Ideal for those with straightforward situations (single state, W-2 + 1099 income) who value mobile convenience. Perfect for rideshare/delivery drivers who need reliable GPS mileage tracking.

Pros

• Best Mobile Experience - Industry-leading mobile app makes tax management effortless on the go; perfect for gig workers rarely at a desk
• Fully Automated Tracking - Bank sync + GPS mileage tracking means nearly zero manual data entry; set it and forget it
• Filing Included - $199/year includes tax preparation and filing; no surprise costs or add-ons for basic filing
• Text Message Support - Unique conversational AI lets you text tax questions and get instant answers; feels like having a CPA on call
• Strong Track Record - 8 years in market, 50,000+ App Store reviews at 4.8 stars; proven reliability

Cons

• Limited Tax Strategy - Focuses on filing, not optimization; won't proactively suggest retirement strategies or entity structure changes
• Expensive for Advanced Needs - Premium ($399) and Business ($1,199) plans are costly compared to hiring a CPA directly
• No Retirement Planning - Doesn't help optimize SEP IRA vs Solo 401k decisions or model contribution strategies

FlyFin: Fully Autonomous AI Tax Service

Overview

FlyFin (founded 2020) positions itself as "the world's first autonomous AI tax service." Their platform uses artificial intelligence trained on millions of tax returns to automatically categorize expenses, calculate quarterly taxes, and prepare your return with minimal human input. Every return is reviewed by licensed CPAs before filing.

Core Value Proposition: "AI prepares your taxes automatically. CPAs review. You just approve."

Pricing (Correct as of January 2026)

Standard Plan: $16/mo or $192/year

• 2024 tax filing with CPAs (federal & state)
• 2024 tax audit insurance
• AI deduction tracking
• Unlimited CPA advice
• Export your data
• Quarterly tax calculator
• ❌ No video calls with CPA
• ❌ No multi-entity support

Premium Plan: $29/mo or $348/year

• Everything in Standard
• ✅ Video call with CPA
• ✅ All entities: S-Corp, K-1s, etc.
• ✅ Quarterly tax support
• ✅ Amend prior year returns
• ✅ Audit resolution support

Business Plan: Pricing not disclosed (custom)

• S-Corp tax filing
• Partnership filing
• Multi-entity support

Key Features

• Autonomous AI Tax Preparation - AI reviews every transaction and prepares tax return automatically
• CPA Review Included - All returns reviewed by licensed CPAs before filing (included in both plans)
• Automatic Bank Sync - Connects to 10,000+ financial institutions
• GPS Mileage Tracking - Background tracking with AI business/personal classification
• Quarterly Tax Calculator - AI calculates estimated payments with push notifications
• Receipt Scanning - OCR with automatic categorization
• Tax Filing Included - Federal + one state included in both plans
• Real-Time Tax Savings Dashboard - Shows current year savings as expenses are categorized

Best For

Tech-savvy professionals who want maximum automation and are willing to pay for it. Ideal for freelancers with multiple income streams or those who want "set it and forget it" tax management. Perfect for high earners ($100K+) who value time over cost savings.

Pros

• Most Autonomous Platform - AI handles categorization, quarterly calculations, and return preparation with minimal user input; closest to true automation
• CPA Review Included - Unlike Keeper which charges extra for CPA support, FlyFin includes licensed CPA review in both plans; provides peace of mind
• Strong Quarterly Features - Proactive notifications with specific dollar amounts for estimated payments; helps avoid underpayment penalties
• Well-Funded Innovation - $50M+ in venture funding means continuous feature development and platform stability
• Unlimited CPA Advice - Both plans include unlimited questions to CPAs throughout the year

Cons

• No Strategic Planning Tools - Focuses on automation and filing, not retirement optimization or proactive tax strategy
• Over-Automation Risks - Some users report AI mis-categorizing expenses; requires periodic review despite "autonomous" claims
• Limited Customization - Because it's designed to be autonomous, less control over tax strategy decisions; AI makes assumptions that might not fit your situation

AlphaTax: Year-Round Tax Planning & Optimization

Overview

AlphaTax is not a tax filing service—it's a comprehensive tax planning and optimization platform designed for freelancers who want to minimize their tax liability year-round, not just file correctly once a year. While Keeper and FlyFin focus on making filing easy, AlphaTax focuses on finding deductions, strategies, and optimizations that filing services often miss.

Core Value Proposition: "Find strategies that save you thousands—not just file your taxes correctly."

Why AlphaTax Doesn't File Taxes

AlphaTax intentionally does not file taxes because:

• Filing is commoditized - Any CPA or service can file your return correctly
• Planning requires different expertise - Finding aggressive-but-legal deductions requires deeper analysis than filing services provide
• Year-round focus - Filing services optimize for April; AlphaTax optimizes for 365 days
• Strategic depth - Retirement optimization, entity structure planning, and scenario modeling aren't part of filing workflows

AlphaTax users typically:

• Work with a CPA who files their return (AlphaTax exports everything)
• Use a separate filing service (TurboTax, FreeTaxUSA) with AlphaTax data
• Have complex situations where strategic planning saves more than filing costs

Pricing

• Monthly: $14/month
• Annual: $99/year (best value)
• Free Trial: 7 days
• Everything Included: No tiers, no upsells, all features included
• 100% Tax Deductible: Your subscription is a business expense

Key Features

• AI Tax Strategy Optimizer - Real-time recommendations with dollar savings (SEP IRA contributions, QBI deductions, home office strategies)
• Retirement Optimizer - Compare SEP IRA vs Solo 401k vs Traditional vs Roth with projected growth scenarios
• Mileage Method Comparison - Calculates BOTH Standard Rate and Actual Expenses, recommends higher deduction (unique feature)
• Quarterly Tax Estimator - Real-time monthly and quarterly estimates with entity-level breakdown
• Receipt & Document AI - Automatically categorizes expenses from photos and PDFs
• Home Office Calculator - Compares Simplified Method vs Actual Expenses with strategic recommendations
• Savings Growth Planner - Projects tax savings + retirement growth across Conservative/Moderate/Aggressive scenarios
• Budget Planner - Monthly and year-over-year income/expense projections
• Multiple Business Tracking - Separate tracking for multiple entities with consolidated tax impact
• Tax Reports - Monthly, quarterly, and annual reports with optimization recommendations
• Professional CPA Export - Comprehensive PDF export compatible with any CPA or filing service

What AlphaTax Finds That Filing Services Miss

1. Retirement Optimization

• Filing services: "Did you contribute to retirement? Enter amount."
• AlphaTax: "Based on your $120K income, contributing $25K to Solo 401k (vs $15K SEP IRA) saves you $3,200 more. Here's why..."

2. Mileage Deduction Method

• Filing services: Standard rate only ($0.70/mile in 2025)
• AlphaTax: Calculates standard AND actual expenses (gas, maintenance, depreciation), recommends whichever saves more (can be $500-2,000 difference)

3. Home Office Strategy

• Filing services: "Do you have home office? Yes/No."
• AlphaTax: "Simplified method saves $1,500. Actual expenses save $2,100. Use actual. Here's the breakdown..."

4. Quarterly Tax Planning

• Filing services: Basic calculator, annual focus
• AlphaTax: "Based on Q3 income spike, increase Q4 payment by $1,200 to avoid underpayment penalty of $180"

5. Entity Structure Planning

• Filing services: File whatever entity you have
• AlphaTax: "At $150K revenue, S-Corp election could save $4,800/year in SE taxes. Here's the breakeven analysis..."

Best For

Freelancers and self-employed professionals who want strategic tax planning, not just filing. Ideal for those with:

• Variable income ($50K-$250K+)
• Multiple income streams or businesses
• Serious retirement planning goals
• Interest in optimizing entity structure (LLC → S-Corp)
• Existing CPA relationship (or planning to hire one)

Perfect for users who understand: Filing services get it done; planning platforms save you money.

Pros

• Finds Strategies Others Miss - Retirement optimization, mileage method comparison, and strategic planning tools filing services don't offer; can save $2K-10K+ annually
• 70-80% Cost Savings - $99/year vs $192-348 (FlyFin) or $199-399 (Keeper); even adding CPA fees ($200-400), total cost is competitive while providing strategic value
• Year-Round Tax Intelligence - Real-time quarterly estimates, monthly strategy reports, proactive recommendations; filing services only engage in Q1
• No Upsells or Hidden Fees - One price, all features included; Keeper/FlyFin charge extra for premium features ($399-1,199)
• Built for Tax Optimization - Every feature designed to minimize tax liability, not just make filing convenient; different design philosophy produces better results

Cons

• No Filing Included - You must file separately (via CPA or other service); Keeper/FlyFin include filing, which is more convenient
• Bank Sync Coming Soon - Automatic bank connections in development; currently requires receipt uploads, PDF statements, or manual entry (Keeper/FlyFin have mature integrations)
• Requires More Engagement - Not "set and forget"; strategic planning requires reviewing recommendations and making decisions (trade-off for better results)

Head-to-Head Comparison

Core Philosophy

Keeper Tax:

• Goal: Make tax filing easy for mobile-first gig workers
• Approach: Automate tracking, handle filing
• Best at: Convenience for straightforward situations

FlyFin:

• Goal: Fully automate tax preparation and filing
• Approach: AI does everything, CPA reviews
• Best at: Hands-off automation for busy professionals

AlphaTax:

• Goal: Minimize tax liability through strategic planning
• Approach: Find every deduction and optimization opportunity
• Best at: Saving money through year-round strategy

What Each Platform Prioritizes

Pricing Comparison (Total Annual Cost)

Software Only (No Filing):

Software + Filing:

Key Insights:

• FlyFin Standard ($192) is cheapest filing included option
• AlphaTax ($99) is cheapest overall if you file separately
• AlphaTax + CPA ($299-499) is competitive with Keeper/FlyFin, but gives you strategic planning they don't offer

Feature Deep Dive

Deduction Discovery

Keeper Tax:

• AI scans bank transactions
• Suggests common deductions
• Chrome extension tracks online purchases
• Focus: Catch expenses you forgot

FlyFin:

• Autonomous AI categorizes everything
• CPA reviews for missed deductions
• Focus: Zero manual categorization

AlphaTax:

• AI suggests deductions based on spending patterns
• Proactive strategy recommendations (not just expense tracking)
• Focus: Find deductions AND strategies to create new deductions

Winner: AlphaTax for strategy; Keeper/FlyFin for convenience

Mileage Tracking

Keeper Tax:

• GPS auto-tracking (best in class)
• Smart learning (home/client patterns)
• Standard rate only ($0.70/mile)
• Result: Accurate tracking, standard deduction

FlyFin:

• GPS auto-tracking
• AI business/personal classification
• Standard rate only
• Result: Automated tracking, standard deduction

AlphaTax:

• Manual tracking (GPS coming soon)
• Calculates BOTH standard AND actual expenses
• Recommends whichever saves more
• Result: More work now, but potentially $500-2,000 higher deduction

Winner: Keeper/FlyFin for current convenience; AlphaTax for savings potential

Quarterly Tax Planning

Keeper Tax:

• Basic quarterly calculator
• Email reminders for deadlines
• Approach: Reactive (you calculate when needed)

FlyFin:

• AI calculates estimates automatically
• Push notifications with specific amounts
• Approach: Proactive automation

AlphaTax:

• Real-time monthly and quarterly estimates
• Entity-level breakdown
• Strategic recommendations ("increase Q4 payment to avoid penalty")
• Budget planning integrated
• Approach: Strategic planning tool

Winner: AlphaTax for depth; FlyFin for automation

Retirement Planning

Keeper Tax:

• ❌ Not offered
• Can track retirement contributions as expenses
• No optimization or comparison tools

FlyFin:

• ❌ Not offered
• Can track retirement contributions
• No strategic planning

AlphaTax:

• ✅ Full retirement optimizer
• ✅ Compares SEP IRA vs Solo 401k vs Traditional vs Roth
• ✅ Projects growth across investment scenarios
• ✅ Recommends optimal contribution amounts
• ✅ Integrated with tax strategy

Winner: AlphaTax (only option with this feature)

Real-World Impact: For a freelancer earning $120K, choosing Solo 401k over SEP IRA can save $3,000-5,000 in taxes annually. Filing services don't help you make this decision.

Real-World Use Cases

Case Study 1: Uber Driver ($45K/year, 30,000 miles)

Profile: Full-time rideshare driver, straightforward income, needs GPS tracking

Best Choice: Keeper Tax Standard ($199/year)

Why:

• GPS mileage tracking is essential (30,000 miles = $21,000 deduction at $0.70/mile)
• Mobile-first design perfect for drivers
• Filing included means one less thing to worry about
• Standard plan includes everything needed

Not AlphaTax because: Manual mileage tracking not realistic for full-time drivers; bank sync not ready

Not FlyFin because: Keeper has better mobile app for drivers; $7/year savings not worth switching

Case Study 2: Freelance Graphic Designer ($85K/year, Home Office)

Profile: Mix of 1099 income, home office, equipment purchases, considering SEP IRA

Best Choice: AlphaTax ($99/year) + CPA or DIY filing

Why:

• Retirement optimizer helps decide SEP IRA contribution amount (could save $3K-5K in taxes)
• Home office calculator ensures correct method (simplified vs actual)
• Quarterly planning prevents underpayment penalties
• Total cost: $99 + $250 CPA = $349 (or $99 + FreeTaxUSA = $149)

Not Keeper/FlyFin because: They don't offer retirement optimization; would pay $192-399 for filing only

Strategic advantage: Retirement planning alone could save $3,000-5,000 annually (30-50x the subscription cost)

Case Study 3: Software Contractor ($150K/year, Considering S-Corp)

Profile: High income, currently sole proprietor, interested in S-Corp election, maxing retirement

Best Choice: AlphaTax ($99/year) + CPA ($400-600)

Why:

• Entity structure planning: S-Corp could save $4,000-8,000/year in self-employment taxes
• Retirement optimizer: Compare SEP IRA ($66K limit) vs Solo 401k ($69K limit in 2026)
• Quarterly planning critical at this income level to avoid penalties
• Total cost: $99 + $500 CPA = $599

Not Keeper/FlyFin because:

• Keeper Business ($1,199) costs more than AlphaTax + CPA
• Neither offers entity structure planning or retirement optimization
• Would pay $1,199 for filing they need anyway

Strategic advantage: S-Corp election alone saves $4K-8K/year; retirement optimization adds $2K-4K

Case Study 4: First-Time Freelancer ($35K/year, Nervous)

Profile: First year self-employed, unsure about deductions, wants hand-holding

Best Choice: FlyFin Standard ($192/year)

Why:

• CPA review included provides peace of mind
• Autonomous AI means less chance of missing deductions
• Unlimited CPA advice for questions
• Filing included = one less thing to figure out

Not AlphaTax because: First-timers need filing included; strategic planning less critical at $35K income

Not Keeper because: FlyFin Standard ($192) cheaper than Keeper Standard ($199) with similar features

Future consideration: Switch to AlphaTax Year 2 once comfortable ($192 → $99 = $93 annual savings)

Case Study 5: Multi-Business Owner ($200K/year, Complex)

Profile: LLC for consulting + rental properties, works with CPA, needs data organized

Best Choice: AlphaTax ($99/year) + Existing CPA

Why:

• Already pays CPA ($800-1,500/year), just needs planning tools
• Multiple business tracking keeps entities separate
• Retirement optimizer critical at high income (Solo 401k $69K contribution limit)
• Budget planner helps with cash flow across businesses
• Total cost: $99/year (CPA already paid for)

Not Keeper/FlyFin because:

• Already has CPA doing filing ($800-1,500)
• Doesn't need another filing service
• Keeper Business ($1,199) duplicates existing CPA relationship

Strategic advantage: Pays for CPA anyway; $99 gets planning tools filing services don't offer

Which Should You Choose?

Choose Keeper Tax If:

• ✅ You're a gig worker (Uber, DoorDash, Instacart) who drives constantly
• ✅ You want best-in-class mobile app and GPS tracking
• ✅ You need end-to-end filing in one platform
• ✅ You value convenience over optimization
• ✅ You have a straightforward tax situation (single state, standard deductions)
• ✅ You're willing to pay $199-399/year for filing included

You'll love Keeper if: Your priority is making tax filing effortless from your phone

Choose FlyFin If:

• ✅ You want maximum automation ("set it and forget it")
• ✅ You value CPA review included in the price
• ✅ You're a busy professional ($75K-150K income) where time > money
• ✅ You want end-to-end filing with AI + human oversight
• ✅ You have multiple income streams or side hustles
• ✅ You're willing to pay $192-348/year for automation + filing

You'll love FlyFin if: You want to think about taxes as little as possible while still getting them done correctly

Choose AlphaTax If:

• ✅ You want year-round tax optimization, not just filing
• ✅ You're serious about retirement planning (SEP IRA, Solo 401k, Roth strategies)
• ✅ You want to minimize taxes legally, not just file correctly
• ✅ You value strategic planning over convenience
• ✅ You already work with a CPA (or plan to) for filing
• ✅ You want to pay $99/year for planning tools
• ✅ You have variable income or multiple businesses
• ✅ You're willing to engage with strategy (not just automation)

You'll love AlphaTax if: You view taxes as a year-round financial strategy and want tools that help you pay less

The Bottom Line

If You Just Want Filing Done:

FlyFin Standard ($192/year) - Cheapest option with filing included + CPA review

If You're a Mobile-First Gig Worker:

Keeper Tax Standard ($199/year) - Best mobile app and GPS tracking

If You Want Strategic Tax Planning:

AlphaTax ($99/year) - Only platform offering retirement optimization and strategic planning tools

The Hidden Value Question

Here's what most people miss:

Keeper and FlyFin will file your taxes correctly. AlphaTax helps you owe less in the first place.

Example:

• With FlyFin: You earn $120K, file correctly, owe $25,000 in taxes ✅
• With AlphaTax: You earn $120K, optimize Solo 401k contribution ($25K vs $15K SEP IRA), use home office actual expenses (not simplified method), plan quarterly payments to avoid penalties → owe $21,500 in taxes ✅

Net result: AlphaTax costs $99. Saves $3,500. 35x ROI.

Filing correctly ≠ Paying the minimum legally possible.

Ready to Optimize Your Taxes?

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If you're serious about strategic tax planning—not just filing—see what AlphaTax's AI Strategy Optimizer can find in potential savings.

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Last Updated: January 2026

Disclaimer: Pricing and features current as of January 2026 and subject to change. This comparison is for informational purposes only. Consult a licensed tax professional for advice specific to your situation.

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