Comparison

Shoeboxed vs SherpaShare

Price, ratings, monetisation and update history for both apps, side by side — with what reviewers say about each.

Head to head
About

Shoeboxed

Effortlessly scan and organize business receipts and track mileage for tax deductions. Automates extraction of vendor, amount, date, and category. Offers automatic background mileage tracking for business trips.

Highlights
  • Automatic receipt scanning
  • Data extraction (vendor, amount, date, category)
  • Searchable receipt storage
  • Automatic background mileage tracking
  • Mileage deduction calculation
  • Mail-in receipt scanning service
  • IRS-ready expense reports
Features
Currently charting
Read full description

STOP CARRYING TWO APPS FOR MILES AND RECEIPTS Our mileage customers ask us the same question: "Wait, does your mileage tracker do my receipts too?" It does. You get UNLIMITED mileage tracking starting at $9/mo AND receipt capture/extraction too. And did you know we're the only receipt app that still scans paper receipts? True. AUTOMATIC, UNLIMITED MILEAGE TRACKING Your phone tracks every business trip in the background. Every evening, we text you a summary: your trips, your miles, your potential deductions. Text back which ones were for work. That's it. No buttons, no screens, no remembering to start tracking. At the current IRS rate of $0.76/mile, 12,000 business miles means $9,120 in deductions. DIGITAL RECEIPTS MADE EASY Photograph any business receipt, our app reads it and extracts the key fields in seconds. Have receipts in email? Just forward them to receipts@shoeboxed.com and they land in your account. Gmail user? Install our Gmail plugin and we read them automatically. We grab the fields the IRS requires: vendor, amount, date, and category. You get every receipt stored, organized, and searchable, ready for tax time or your accountant. PAPER RECEIPTS If you have a pile of paper receipts, just tap the Magic Envelopes icon in the app and: - We mail you a prepaid envelope - You stuff it with paper receipts and drop it in the mail - Real people in Durham, NC scan every receipt into your account SELF-EMPLOYED? YOU'RE PROBABLY MISSING THOUSANDS IN DEDUCTIONS. Most business owners miss deductions they've earned, simply because tracking receipts and mileage is a pain. Shoeboxed does the tracking and the sorting for you. REAL PEOPLE ANSWER THE PHONE Our support team works out of Durham, North Carolina. Call with a question and a real person answers. Amy, Jennifer, and Morgan have helped Shoeboxed customers for years, and they still pick up the phone. IRS-READY EXPENSE REPORTS One tap makes an IRS-ready expense report. Date, destination, distance, business purpose: everything the IRS asks for, captured for you and ready to send. HELPING BUSINESSES SAVE ON TAXES SINCE 2007 Featured in Forbes, The New York Times, and The Wall Street Journal. Built for self-employed, LLC owners, small business owners, owner/operator truckers, coaches, therapists, contractors, consultants, realtors, and every business owner who drives for work and has receipts to track. START YOUR TRIAL: • Starter ($9/mo): 50 scans + unlimited mileage tracking • Pro ($29/mo): 250 scans + unlimited mileage tracking • Plus ($79/mo): 1,000 scans + unlimited mileage tracking Terms of Use (EULA): https://www.apple.com/legal/internet-services/itunes/dev/stdeula/

About

SherpaShare

This app helps rideshare drivers maximize their earnings and minimize tax burdens. It automatically tracks mileage and expenses, provides smart route planning, and connects drivers with a supportive community. Access real-time data and exclusive savings to boost your income.

Highlights
  • Automatic mileage tracking
  • Expense tracking
  • Smart route planning
  • Driver community connection
  • Real-time data intelligence
  • IRS-compliant mileage log
Features
Read full description

Do you drive for Uber, Lyft or another platform? Use the ultimate rideshare driver assistant to boost your earnings 30% or more with automatic mileage tracking, expense tracking, and smart driver Pro Tools that help you plan the best routes and get more pings. Start your free 14-day trial today! HIGHLIGHTS: - SherpaShare automatically tracks your driving mileage for business and tax purposes using advanced tracking technology. You'll get the tax deduction you deserve with almost no effort. Our users save on average $6,900 per year! Use our web dashboard to manage your finances and expense in one place. - SherpaShare Pro Tool set helps you make more money with real time insight about when and where to drive and how to drive. - SherpaShare provides deep analytics for your work so you can stay top of your job. - SherpaShare connects you with our large driver community and chat with other drivers. Get real-time info, help, and support. - SherpaShare gives you exclusive access to huge driver saving on wears and gears. FEATURES: • Automatically tracks all your mileage using your phone’s GPS • Battery-friendly • Makes tracking revenue and expenses effortless • IRS-compliant mileage log • Securely backed-up in the cloud with all your financial information in one place, and accessible from every device. • Connects you with a community of other drivers for insights into real-time road conditions, work-related questions, and stories. • Real-time data intelligence for your ride sharing gig • Access to more money making opportunities GET THE TAX DEDUCTION YOU DESERVE: If you use your personal vehicle for work, every mile you drive is worth 53.5 cents as a tax deduction or mileage reimbursement. Keeping a manual mileage log is time-consuming and a major hassle. With SherpaShare's advanced tracking technology, drivers can log more miles due to the improved accuracy and "always on" nature of our service. SherpaShare also gives you peace of mind while allowing you to focus on maximizing your earnings. • If you drive 10,000 miles a year, your mileage deduction would be $5,350. That’s 10,000 miles x $0.535 (standard mileage rate) = $5,350. That’s money you won’t need to pay in taxes or money that you get back from your employer as a reimbursement! • The average SherpaShare customer is logging $6,900 in mileage deductions or reimbursements. • Integrates seamlessly with sherpashare web dashboard using the same login. • All your mileage and expenses are securely backed up in one place. BECOME A SHERPASHARE MEMBER: Upgrade to our premium membership to access all of our features for $5.99/month recurring or $59.99/year recurring. "A 12-mile business drive earns you $6.48 in deductions, more than the cost of SherpaShare premium membership for one month." " Your SherpaShare subscription can be reimbursed or tax-deducted as a business expense” If you choose to subscribe, you will be charged a price according to the selected plan. The price will be shown in the app before you complete the payment. Monthly subscriptions renew each month, and annual subscriptions renew each year unless auto-renew is turned off at least 24 hours before the end of the current subscription period. Your iTunes account will automatically be charged within 24 hours prior to the end of the current period and you will be charged for one month at a time. You can turn off auto-renew at any time from your iTunes account settings. BATTERY CONSUMPTION: Continued use of GPS running in the background can dramatically decrease battery life. SherpaShare Tracker has been designed to limit iOS GPS usage, so it uses a nominal amount of battery power. HAVE A PROBLEM? - CONTACT US WITH QUESTIONS OR CONCERNS • Email: hello@sherpashare.com • Twitter: www.twitter.com/sherpashare • Facebook: www.facebook.com/sherpashare • Term: www.sherpashare.com/terms • Privacy: www.sherpashare.com/privacy

Screenshots

Shoeboxed4 screens
SherpaShare4 screens

Verdict

The call

Shoeboxed and SherpaShare both sit at 4.5 stars, but that hides the real split: 60% of Shoeboxed's written reviews are positive against 46% of SherpaShare's. Shoeboxed also leads on chart position (#138 vs unranked). SherpaShare's advantage is iOS requirement (8.0 vs 15.0). On price, rating, ratings volume and update cadence there is nothing between them.

Scored on Price · Rating · Positive reviews · Number of ratings · Update frequency · Ads · In-app purchases · Monetization · Best chart rank · Devices · Requires iOS

CostPrice · In-app purchases · Ads · Monetization

Both are free to download. Shoeboxed sells 10 in-app purchases, starting at $7.39 per month and SherpaShare sells 2 in-app purchases, starting at $5.99 per month. Whichever you choose, the download price is not the number that matters.

ReceptionRating · Positive reviews · Number of ratings

On the App Store both sit at effectively the same score — 4.5 for Shoeboxed against 4.4 for SherpaShare. Both are backed by a comparable volume of ratings — 1.8K and 1.9K respectively. Written reviews are what separate them: 60% of Shoeboxed's written reviews are positive against 46% of SherpaShare's.

UpkeepUpdate frequency

Shoeboxed ships an update every 2 weeks, SherpaShare weekly. The most recent releases landed on October 31, 2026 and November 1, 2026 respectively.

Scorecard3 real differences · 8 level
Shoeboxed versus SherpaShare: the parameters behind the verdict, then further details
ParameterShoeboxedSherpaShare
PriceFreeFree
Rating4.5 (1.8K ratings) — better4.4 (1.9K ratings)
Positive reviews60.0% of reviews — better46.5% of reviews
Number of ratings1.8K1.9K — better
Update frequencyEvery 2 weeksWeekly — better
AdsNoNo
In-app purchasesYesYes
MonetizationFreemiumFree with in-app purchases
Best chart rank#138 — better—
DevicesiPhone, iPad, iPod — betteriPhone, iPod
Requires iOS15.08.0 — better
Further details — not scored
Size30 MB93 MB
Age rating4+17+
DeveloperShoeboxed.comSherpaShare, Inc

Customer experience

Shoeboxed

All ratings1,811 ratings
Positive88.6%
Neutral3.8%
Negative7.6%
Written reviews215 reviews
Positive60.0%
Neutral8.4%
Negative31.6%

SherpaShare

All ratings1,898 ratings
Positive84.0%
Neutral5.0%
Negative11.0%
Written reviews114 reviews
Positive46.5%
Neutral9.6%
Negative43.9%

User reviews

Shoeboxed

From 1.8K App Store ratings

What we love

  • ⭐ Highly recommended
  • 🚀 Efficient receipt management
  • 👍 Easy to use
  • 🤝 Excellent customer service
  • 💰 Helpful for taxes and expenses

Room to improve

  • 🐛 Glitchy app updates
  • 🕰️ Slow processing of receipts
  • 🔍 Inconsistent data capture
  • 🔒 Account and data issues
  • 💰 Expensive paid plans

SherpaShare

From 1.9K App Store ratings

What we love

  • 🚀 Automatic mileage tracking
  • 📊 Useful expense and mileage reports
  • 🗓️ Easy categorization of trips
  • 💰 Helps save money on taxes

Room to improve

  • 🔍 Difficulty cancelling subscription
  • 🔇 Poor customer support
  • 🐛 Tracking issues and data loss
  • 🔋 High battery consumption

Bugs and requests

Shoeboxed

Reported bugs

4 issues
  • Receipts disappearing or not syncing
  • Login and account creation problems
  • Slow performance and app crashes
  • Incorrect data extraction from receipts

Requested features

5 requests
  • Improved mileage tracking
  • Faster receipt processing
  • More customization options
  • Better integration with accounting software
  • Ability to edit/correct receipt data

SherpaShare

Reported bugs

3 issues
  • App randomly stops tracking mileage
  • Errors during sign-up process
  • Inconsistent data syncing across devices

Requested features

4 requests
  • Ability to manually enter trips
  • Integration with accounting software
  • More detailed trip information
  • Improved heat map and location features

In-app purchases

10 purchases

Shoeboxed

Subscriptions10
  • Starter Plan1 Month trial$7.391 Month
  • Starter Monthly7 Days trial$9.001 Month
  • Shoeboxed Mobile Premium1 Month trial$14.951 Month
Show 7 more
  • Lite Plan1 Month trial$14.951 Month
  • Shoeboxed Mobile Pro1 Month trial$24.991 Month
  • Pro Plan1 Month trial$24.991 Month
  • Pro Monthly7 Days trial$29.001 Month
  • Plus Monthly7 Days trial$79.001 Month
  • Starter Annual7 Days trial$97.001 Year
  • Pro Annual7 Days trial$290.001 Year
2 purchases

SherpaShare

Subscriptions2
  • SherpaShare Membership Premium Subscription$5.991 Month
  • SherpaShare Membership Premium Subscription$59.991 Year

Questions

Is Shoeboxed free?
Shoeboxed is free to download, with in-app purchases available.
Is SherpaShare free?
SherpaShare is free to download, with in-app purchases available.
Which has better reviews, Shoeboxed or SherpaShare?
Shoeboxed is rated higher. Shoeboxed averages 4.5 out of 5 from 1.8K ratings, while SherpaShare averages 4.4 from 1.9K ratings.
Do Shoeboxed or SherpaShare have ads?
Neither Shoeboxed nor SherpaShare shows ads.
Which is updated more often, Shoeboxed or SherpaShare?
Shoeboxed ships an update every 2 weeks, and SherpaShare weekly. Most recently, Shoeboxed was updated on October 31, 2026 and SherpaShare on November 1, 2026.

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