Keeper vs FlyFin: two AI deduction engines for freelancers, compared
Both link your bank accounts and let a model hunt write-offs year-round. They differ on what happens after the AI finishes.
Keeper and FlyFin solve the same problem with near-identical mechanics: connect bank and card accounts, let a model classify every transaction against deductible categories continuously, then file a return that is largely assembled before filing season opens. Both are AI-native, both are US-only, and both are built for 1099 income rather than W-2 salary.
The interesting divergence is what surrounds the model. Keeper leans on the deduction-finding itself as the product and reports users surfacing roughly 168 write-offs on average. FlyFin leans on the claim of near-total automation — it says its engine handles up to 95% of prep work — and puts licensed CPA review behind every return as the guarantee.
| Product | Regions | Built on AI | HQ |
|---|---|---|---|
| Keeper | US | AI-native | San Francisco, US |
| FlyFin | US | AI-native | San Jose, US |
How each one's AI actually works
Keeper runs a GPT-4 model fine-tuned on US tax law. That fine-tuning matters for the part of the job that is not classification: an in-app assistant answers tax questions in the context of your own transactions, rather than answering generically. Ambiguous purchases are surfaced for a yes/no confirmation instead of being silently guessed.
FlyFin's engine is also GPT-4-based and purpose-built for tax questions. Its framing is throughput — automate the preparation work, then use CPAs as the accuracy backstop. Where Keeper sells you a tool that finds money, FlyFin sells you a finished return with professional review attached.
How much traction each has
Neither product is a mainstream incumbent, so scale is worth weighing before you commit a filing season to one. Keeper's iOS app has passed 750,000 downloads; FlyFin reports over 250,000 users.
Both therefore have a real base, but both are far smaller than the established filing products, and support capacity tends to track that. If you expect to need help in the last week before a deadline, that is the number to think about.
Where each one fits
If your situation is straightforward 1099 income and the value you want is finding deductions you would otherwise miss, Keeper's model plus its in-app assistant is the tighter fit. If you would rather hand the whole return over and have a CPA sign off on the automation's output, FlyFin is built around that promise.
Neither is the right tool if you have moved past sole-proprietor simplicity. Once an S-corp election, payroll, or multi-entity structure is in play, the automation you need is different — that is Lettuce's territory, and worth comparing before committing.
The verdict
Frequently asked
- Is Keeper or FlyFin better for finding tax deductions?
- Both scan linked bank and card transactions continuously.
- Do Keeper and FlyFin both include a human tax professional?
- Yes, in different ways. Keeper hands the completed return to a human professional for review and e-filing on paid plans. FlyFin puts licensed CPA review behind every return as a core part of its offer.
- Can these tools file state as well as federal returns?
- Both are US filing products covering federal and state returns. Neither operates outside the United States, so freelancers elsewhere should look at the regional options instead.
Profiles referenced
Keeper
keepertax.comModern US tax platform combining AI and human accountants for freelancers, S-Corps, rentals, and investments: write-off detection, e-file, year-round support; IRS authorized e-File Provider.
FlyFin
flyfin.taxAI plus CPA tax filing for freelancers, self-employed, and 1099 & W-2: AI finds deductions and builds the return; dedicated CPA reviews and files federal and state; quarterly estimator and audit insurance claims.