1099 Pilot
Know What You Owe Quarterly
Free · In‑App Purchases · Designed for iPad. Not verified for macOS.
Your quarterly tax number, always up to date. Track income, deductions & deadlines — free. No accounts, no servers, no April surprises.
Stop guessing what you owe the IRS.
If you're a freelancer, contractor, or gig worker, you're supposed to pay taxes four times a year. Most people either overpay (and lose cash flow) or underpay (and get hit with penalties). 1099 Pilot fixes that.
Log your income and expenses as they happen, and your quarterly tax estimate updates instantly. Track mileage, scan receipts, plan scenarios, and stay ahead of every deadline. No accounting degree required.
WHAT YOU GET FOR FREE:
• Unlimited income & expense tracking
• Deduction checklist so you never miss one
• Monthly income vs. expense chart
• Quarterly deadline reminders
• Up to 5 mileage trips per month
• Smart dashboard insights & daily tax tips
WHAT PRO UNLOCKS ($4.99/mo or $29.99/yr):
• Your exact quarterly tax estimate
• Full tax breakdown (federal, state, self-employment)
• Receipt scanning with image storage — point your camera, done
• What-If scenario planner — see how any decision changes your tax bill
• Unlimited mileage tracking at the current IRS rate
• Recurring templates for monthly subscriptions & regular payments
• CSV export to hand your CPA a clean file
• Import bank statements via CSV in seconds
• 1040-ES payment voucher with IRS Direct Pay links
• Year-over-year comparison with charts
• Profit & Loss report by category
• Tax Prep checklist to walk you through filing season
• Tax savings tracker — see how much your deductions save
• All 50 state tax estimates
• Premium themes & milestone celebrations
• Weekly expense & monthly deduction reminders
BUILT FOR REAL FREELANCERS:
• Uses actual IRS tax brackets and self-employment rates
• Handles the 50% meals rule, SE tax deduction, and standard deductions automatically
• Mileage tracker at $0.70/mile — 5,000 miles = $3,500 in deductions
• Supports all 50 states
• Works for Uber drivers, Etsy sellers, consultants, designers, developers — anyone with 1099 income
YOUR DATA STAYS YOURS:
All data is stored on your device. No accounts, no servers, no tracking. Optional iCloud sync uses Apple's encrypted infrastructure. We never see your financial data.
THIS IS NOT A TAX FILING APP.
1099 Pilot is your co-pilot — it tells you what you owe so you're never surprised. You still file with TurboTax, your CPA, or however you normally do it. We just make sure you're ready.
The average IRS underpayment penalty costs more than a full year of Pro. One missed deduction pays for it ten times over.
WHAT'S NEW:
• Mileage Tracker — log business trips, auto-calculate deductions at the IRS rate
• What-If Scenario Planner — see how buying equipment or maxing a SEP IRA changes your tax bill
• Receipt Image Storage — save photos with expenses for audit protection
• Recurring Templates — automate monthly subscriptions and regular payments
• CSV Bank Import — bulk-import transactions from bank statements
• Payment Voucher — 1040-ES reference with IRS payment links
• Year-over-Year Comparison — track growth with side-by-side charts
• Profit & Loss Report — professional breakdown by category
• Tax Prep Checklist — personalized filing guide from January through April
• Smart engagement reminders to keep you on track
https://1099pilot.site/terms
Terms of Use (EULA): https://www.apple.com/legal/internet-services/itunes/dev/stdeula/
Ratings & Reviews
- This app hasn’t received enough ratings or reviews to display an overview.
FREE TIER IMPROVEMENTS
• Tax breakdown (federal income tax + self-employment tax) now visible to all users — not just Pro
• "Tax Saved" and "Payments Made" stats now free for everyone
• Upgrade prompt moved to the bottom of the screen, so you see your data first
SMARTER ALERTS
• Penalty warnings now have two tiers: minor (orange) vs. significant (red) — small underpayments no longer trigger a scary critical alert
• New alert: if you've logged income but no expenses after 30+ days, the app estimates what you might be missing
• Savings target now calculates based on your next quarterly deadline, not the end of the year
• Year-end projections now require 60 days of data and show how many days the estimate is based on
TAX ACCURACY FIXES
• Married filing jointly now gets correctly scaled state tax brackets for CA, NY, NJ, OR, MN, CT, and HI (was using single-filer rates)
• Additional Medicare tax threshold corrected to $250k for MFJ (was $200k for all filers)
DATA ENTRY IMPROVEMENTS
• Meals expense note now clarifies: enter the full amount — the app applies the 50% rule automatically
• Large amounts like $1,500,000 no longer appear as "1.5e+06" when editing an entry
ONBOARDING & SETUP
• Onboarding shortened from 5 pages to 4 — ends on a positive note instead of a legal disclaimer
• Skipping the state selection now shows a clear note: "Defaults to California — change anytime in Settings"
• Filing status is now required during setup (was skippable, which caused tax estimates to use wrong brackets)
BUG FIXES
• Export failures now show an error message instead of silently doing nothing
The developer, Angela Freeman, indicated that the app’s privacy practices may include handling of data as described below. For more information, see the developer’s privacy policy .
Data Not Collected
The developer does not collect any data from this app.
Accessibility
The developer has not yet indicated which accessibility features this app supports. Learn More
Information
- Seller
- Angela Freeman
- Size
- 2.5 MB
- Category
- Finance
- Compatibility
Requires iOS 17.0 or later.
- iPhone
Requires iOS 17.0 or later. - iPad
Requires iPadOS 17.0 or later. - Mac
Requires macOS 14.0 or later and a Mac with Apple M1 chip or later. - Apple Vision
Requires visionOS 1.0 or later.
- iPhone
- Age Rating
4+
- 4+
- In-App Purchases
Yes
- 1099Pilot Pro Monthly $4.99
- 1099Pilot Pro Yearly $29.99
- Copyright
- © 2026 1099Pilot