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AI-assisted tax filing for freelancers and self-employed workers

FlyFin helps freelancers, self-employed workers, and small business owners file taxes with AI plus CPA review. It scans expenses for deductions, organizes documents, and has CPAs prepare and e-file returns.

Agenticness = how independently a tool can take action, scored across 9 dimensions. Scored independently by David Kooi, Skylark Creations — see full rubric →

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Paid
iOS
B2B
B2C
No-Code
Cloud Hosted
Copilot (Human-in-Loop)
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Recent activity

What's happened with FlyFin lately

  • Score change
    Rubric upgrade v3_0 → v3.1: score 7/32 → 6/3676/36(-1)

    Rubric upgrade: agenticness v3.0 (8 dims, /32) → v3.1 (9 dims, /36). Adds Dim 9 (Operator Sovereignty), splits Dim 6 into 6a/6b lenses, tightens Dim 4 autonomous-retry distinction. Not a product change — score shift reflects new dimension + recalibrated rubric, not a change in the tool. Fanout suppressed.

    See the news that prompted this

News mentions sourced from our news feed; score changes from periodic re-evaluations.

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About

What It Is

FlyFin is an AI-assisted tax filing service focused on freelancers, self-employed people, 1099 workers, and some small business tax situations. It combines automated deduction discovery with CPA-led tax preparation, so the product is aimed at people...

What to Know

FlyFin looks more like a managed tax filing service than a pure autonomous agent. The AI appears to handle deduction discovery and document organization, but humans still do the actual tax preparation and filing. That makes it useful if you want...

Key Features
Scans expenses and identifies deductions across 200+ categories
Uploads tax documents and builds a tax profile for CPA review
Prepares federal and state tax returns with CPA assistance
E-files completed tax returns
Supports multiple tax situations including W-2, 1099, K-1, sole proprietorships, LLCs, S-corps, C-corps, partnerships, and trusts
Use Cases
A freelancer wants help maximizing deductions and filing a 1099 return
A self-employed consultant needs federal and state returns prepared by a CPA
A small business owner wants AI to organize expenses before tax prep
Agenticness: Guided Assistant

Executes tasks you assign, one step at a time, within narrow domains.

High evidence
Last evaluated: May 22, 2026

Dimension Breakdown

Action Capability
Autonomy
Planning
Adaptation
State & Memory
Reliability
Interoperability
Safety
Operator Sovereignty

Categories

Pricing

Pricing not publicly available.

Details
AddedMarch 31, 2026
RefreshedMarch 31, 2026
Agenticness
Quick Facts
DeploymentCloud-hosted
AutonomySemi-autonomous
Model supportSingle model
Open sourceNo
Team supportSmall team
Pricing modelSubscription
Interfaceweb
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