Ranking

Best AI Apps for Freelancers’ Quarterly Tax Estimates (US)

Task: Know what to set aside and pay each quarter on 1099 income (US)Last checked: Desk-research score v1 · checked 2026-10-22

Short answer: Found scores 8.2/10 on the Free plan ($0/mo). Free running estimate, if you bank with Found.

#ToolScoreQualitySpeedPriceEaseVerdict
1Found → profileScored on: Free$0 (Found Plus $35/mo or $315/yr)Free plan. 30-day trial of Plus8.2691010Free running estimate, if you bank with Found. Why?
2Keeper → profileScored on: Premium$199/yr Standard ($399/yr Premium)No free plan. 14-day trial6.68647Pay quarterly plus a filed return, for $399 a year. Why?
3FlyFin → profileScored on: Premium$29/mo billed $348 annually (Premium)Start free; pay when you file6.18259CPA-heavy; the estimate is a calculator, not a savings account. Why?

Scores come from public evidence (vendor pricing pages, help docs, feature pages), checked 2026-10-22. We have not run hands-on tests yet. They are planned, and these scores will be updated. See every source ↓

Underpay your quarterly estimates and the IRS charges a penalty; overpay and you starve your own cash flow. We score the cheapest plan in each app that keeps a running estimate. This is software research, not tax advice.

How this ranking was scored: desk research, version 1, checked 2026-10-22. We checked each tool against the public checklist below using vendor pricing pages, help-center docs and feature pages. Every point links to its source under “Why each tool scored what it did”. Plan scored: Cheapest plan with quarterly estimated-tax support (a running estimate, a quarterly calculator or quarterly payments). US federal taxes only. Annual price per month when no monthly price is published.

We have not run hands-on tests yet. They are planned with the fixture in tests/taxes/scenario-01.md, and scores will be updated when they are done.

Why each tool scored what it did

Each Quality and Speed check is worth 2 points (2 = verified on the plan scored, 1 = limited, add-on, higher tier or conflicting docs, 0 = not available or not verifiable). Price bands, monthly list price: $0 = 10 · ≤$10 = 9 · ≤$15 = 8 · ≤$20 = 7 · ≤$25 = 6 · ≤$30 = 5 · ≤$40 = 4 · ≤$50 = 3 · ≤$75 = 2 · more = 1.

Quality checklist
  1. Running tax estimate from your actual income and expenses
  2. Automatic write-off detection
  3. Pay or schedule quarterly estimated payments in the app
  4. Access to a human tax pro on the plan
  5. Annual return filing included
Speed checklist
  1. Connects your bank and card accounts
  2. Receipt scanning
  3. Automatically sets money aside for taxes
  4. Official iOS and Android apps
  5. Mileage or home-office deduction tracking
1. FoundQ 6 · S 9 · P 10 · E 10 → 8.2

Plan scored: Free ($0/mo). Free plan includes real-time tax estimates; Found Plus ($35/mo) adds in-app quarterly payments. Requires opening a Found business account. found.com

Quality 6/10

  • 2Running tax estimate from your actual income and expenses. Real-time tax estimates found.com
  • 2Automatic write-off detection. Write-off identification on Free found.com
  • 1Pay or schedule quarterly estimated payments in the app. In-app quarterly federal payments are Found Plus found.com
  • 0Access to a human tax pro on the plan. No tax pro access listed found.com
  • 1Annual return filing included. Generates Schedule C; does not file your return found.com

Speed 9/10

  • 1Connects your bank and card accounts. It is your bank account; importing other banks and cards is Plus found.com
  • 2Receipt scanning. Scan receipts on Free found.com
  • 2Automatically sets money aside for taxes. Taxes Pocket saves automatically found.com
  • 2Official iOS and Android apps. App Store and Google Play apps linked from found.com found.com
  • 2Mileage or home-office deduction tracking. Mileage and home office tracking on Free found.com

Ease 10/10

  • 4Free plan / trial. Free plan covers the estimate found.com
  • 2Self-serve, no sales call. Self-serve signup and cancel; no sales call needed for this plan found.com
  • 2Nothing to install. Runs in the browser; nothing to install found.com
  • 2Single seat allowed. Can be bought for a single user found.com
2. KeeperQ 8 · S 6 · P 4 · E 7 → 6.6

Plan scored: Premium ($33.25/mo). Quarterly tax payments are Premium only: $399/yr ($33.25/mo). Standard ($199/yr) has no quarterly support. keepertax.com

Quality 8/10

  • 0Running tax estimate from your actual income and expenses. Running estimate not described on the pricing page keepertax.com
  • 2Automatic write-off detection. AI finds and categorizes deductions keepertax.com
  • 2Pay or schedule quarterly estimated payments in the app. Pay quarterly taxes: schedule estimated payments keepertax.com
  • 2Access to a human tax pro on the plan. Meet with a tax pro keepertax.com
  • 2Annual return filing included. Federal + up to 2 state returns, signed by a pro keepertax.com

Speed 6/10

  • 2Connects your bank and card accounts. Connect unlimited accounts keepertax.com
  • 2Receipt scanning. Scan receipts keepertax.com
  • 0Automatically sets money aside for taxes. No automatic tax savings listed keepertax.com
  • 2Official iOS and Android apps. Desktop and mobile keepertax.com
  • 0Mileage or home-office deduction tracking. Mileage tracking marked coming soon keepertax.com

Ease 7/10

  • 1Free plan / trial. 14-day trial; charged unless you cancel keepertax.com
  • 2Self-serve, no sales call. Self-serve signup and cancel; no sales call needed for this plan keepertax.com
  • 2Nothing to install. Runs in the browser; nothing to install keepertax.com
  • 2Single seat allowed. Can be bought for a single user keepertax.com
3. FlyFinQ 8 · S 2 · P 5 · E 9 → 6.1

Plan scored: Premium ($29/mo). Premium is $29/mo billed $348 annually; the Standard price is not shown on FlyFin’s own plan page, so it is not scored. flyfin.tax

Quality 8/10

  • 2Running tax estimate from your actual income and expenses. Quarterly tax estimator from your deductions & income flyfin.tax
  • 2Automatic write-off detection. A.I. deduction tracker flyfin.tax
  • 0Pay or schedule quarterly estimated payments in the app. Quarterly payments not documented flyfin.tax
  • 2Access to a human tax pro on the plan. Unlimited CPA advice + video call flyfin.tax
  • 2Annual return filing included. CPA-prepared federal & state filing flyfin.tax

Speed 2/10

  • 1Connects your bank and card accounts. Automatic financial tracker; account linking not spelled out flyfin.tax
  • 0Receipt scanning. Receipt scanning not documented flyfin.tax
  • 0Automatically sets money aside for taxes. No automatic tax savings flyfin.tax
  • 0Official iOS and Android apps. Mobile apps not documented on the site flyfin.tax
  • 1Mileage or home-office deduction tracking. Detects car, mileage and home-office deductions flyfin.tax

Ease 9/10

  • 3Free plan / trial. Start free; pay when you file flyfin.tax
  • 2Self-serve, no sales call. Self-serve signup and cancel; no sales call needed for this plan flyfin.tax
  • 2Nothing to install. Runs in the browser; nothing to install flyfin.tax
  • 2Single seat allowed. Can be bought for a single user flyfin.tax

Tools in this ranking

Hands-on fixture (planned): tests/taxes/scenario-01.md · How we score →