Shoeboxed Review 2020

Paper receipts cluttering your office? Mail them to Shoeboxed for simple scanning and categorization before tax time.

out of overall
Easy outsourced receipt digitization
Unlimited online document storage
Receipts automatically sorted by tax category
Double-entry accounting with two most expensive plans only

Remember that old box, filing folder, or cabinet you’d fill with receipts, promising to categorize them someday and crossing your fingers that you wouldn’t get audited in the meantime? Good news: your stashing days are over. There’s an app for that now—or, in the case of Shoeboxed, an app and then some.

A Shoeboxed subscription includes prepaid envelopes that you stuff full of old receipts (and any other paper business documents) and mail to the company, which scans, uploads, and categorizes your expenses. You can also scan and upload paper receipts yourself and generate on-the-go expense reports with the company’s free mobile app.

Intrigued? Our Shoeboxed review can help you decide if the company’s receipt scanning is right for your business—or if you need to look elsewhere for a better fit.

Shoeboxed plans and pricing 2020
Plan nameStarting priceDigital documentsPhysical documentsMagic envelopesLearn more
Startup$23/mo.*50/mo.25/mo.1/mo.View Plan
Professional$47/mo.*150/mo.150/mo.UnlimitedView Plan
Business$71/mo.*3,000/mo.300/mo.UnlimitedView Plan
Data effective 2/26/20. At publishing time, pricing and features are current but are subject to change. Offers may not be available in all areas.
*Price when billed annually; pay-per-month pricing costs an additional 20% per month.

Some of us are organized by habit or nature, and some of us . . . well, we just aren’t. But businesses thrive on good organization, and your fiscal ducks—your financial info and documents—had better be in a row when the bank or IRS comes calling.

That’s where Shoeboxed comes in. Each Shoeboxed plan includes a certain number of Magic Envelopes, or prepaid envelopes you can fill with as many paper documents as they can hold. Once they receive the envelope, the Shoeboxed team scans and digitizes your documents so you don’t have to. Even better, they categorize the scanned documents and store them for you on an easy-to-search database.

How does Shoeboxed categorize your receipts?

Shoeboxed’s algorithm sorts each receipt into one of 15 tax categories, ranging from fuel to groceries. Note that Shoeboxed only categorizes receipts. All other scanned documents simply become uncategorized PDFs.

But Shoeboxed does more than quickly clearing your desk of old paperwork and storing it securely online. It also offers features like these:

  • Automatic mileage tracker for travel expense reimbursement
  • Integration with QuickBooks, Wave, Xero, and other accounting solutions
  • Expense report generation
  • On-the-go receipt scanning and archiving with the free mobile app
  • Business card scanning to create a contact database

Shoeboxed pricing and plan information

Shoeboxed offers three plans geared at different types of businesses: Startup, Professional, and Business. All three plans include unlimited document storage and unlimited users, but they vary in how many documents you can scan, upload, and store per month.

Startup, the cheapest plan, allots users just one Magic Envelope a month. You can upload only 50 documents yourself and submit only 25 physical documents to the Shoeboxed team for digitization. If all of your documents won’t fit in one envelope, you can still send them in—just know you’ll be paying the postage yourself.

Money-saving tip: Pay annually, not monthly

If your budget can accommodate it, consider paying for Shoeboxed annually, not monthly—the annual total is 20% less than the month-by-month total.

Since the Startup plan’s document limit is so low, it works best for freelancers, contractors, and solopreneurs. If you exceed the document limit, you’ll be charged an extra $0.40 per digital document and $0.50 per physical document. And with Startup, you’ll pay a small fee—probably for shipping, though the website doesn’t specify—to get your documents shipped back to you.

Business and Professional, the two pricier plans, include unlimited prepaid envelopes and free document returns. Only the Professional and Business plans include QuickBooks Online integration.

Don’t vibe with any of these plans? You can work with Shoeboxed to create a custom one.

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Shoeboxed pros and cons

  • IRS-approved receipts
  • Gmail receipt syncing
  • Automatic mileage tracking
  • Limited functionality beyond receipts and mileage tracking
  • Poor Android app ratings

Shoeboxed pros

The digital receipts Shoeboxed creates are IRS approved, which means that if your business is audited, the IRS accepts the accuracy and legitimacy of digitized Shoeboxed files.

Even if you never get audited, you can benefit from the simplification Shoeboxed provides. For instance, if you sync Shoeboxed with your Gmail account, Shoeboxed automatically imports data from any receipts that get emailed to you and sorts them into the right category. It also uses your phone’s GPS for mileage tracking. At the end of a business trip, the app turns the tracked miles into a receipt and categorizes it accordingly.

What does that mean in time-saving terms? You won’t have to sort through your inbox to pull and catalogue receipts yourself. And instead of tallying up trip costs every time you stop for gas, you can focus on the trip itself and let Shoeboxed handle the rest.

Shoeboxed's receipt-scanning app

The Shoeboxed receipt-scanning app comes free with each plan. You can use it to scan and upload receipts or to generate on-the-go expense reports with receipt screenshots attached. Your app experience might depend on what type of phone you own. The iPhone app has 1.3K reviews with an average star rating of 4.5,1 but the Google Play app has just a few hundred reviews with an average of 2.5 stars.2

Shoeboxed cons

Shoeboxed doesn’t include employee reimbursement options—which isn’t necessarily an automatic con. After all, small-business owners with dozens of employees aren’t the only people who need organizational help; freelancers, contractors, and sole proprietors do too. Still, if you’re looking for something with more robust business support, including corporate card management and employee reimbursement, you’d be better off with a receipt-scanning app like Expensify.

And according to reviews on Google Play store, the free Shoeboxed app leaves a little to be desired; the images it captures aren’t crystal clear and can take several shots to focus correctly.

Shoeboxed FAQs

How much does Shoeboxed cost?

After the 30-day free trial, Shoeboxed starts at $23 a month if you pay annually or $29 if you pay month to month.

Is Shoeboxed free?

Nope. Once your 30-day free trial is up, Shoeboxed starts at $23.

What is the best way to keep receipts?

Ink fades, receipts tear, and prices are easily lost in the clutter. In our book, digitizing receipts is the way to go—not just because they’re easier to save and sort, but also because they make audits, tax filing, and employee reimbursement as hassle-free as can be.

How does Expensify compare to Shoeboxed?

Both Expensify and Shoeboxed are receipt-scanning apps, but they serve two vastly different purposes. Expensify aims to simplify expense management for everyone from freelancers to the biggest businesses; it allows for next-day employee reimbursement, end-of-the-month expense reports, and corporate card management.

Meanwhile, Shoeboxed is geared towards business owners who need a quick way to clear away paper clutter. It offers basic expense tracking, but it isn’t an all-out expense management system like Expensify.

The takeaway

So is Shoeboxed a good receipt scanner for your company? The answer depends less on your industry and business size and more on your personality, needs, and office organization. If you’re fine handling digitization and organization on your own, Shoeboxed might be a little too basic for you. But if you’re sick of paper receipts cluttering your office (and digital ones in your inbox), this receipt scanner and organizer is a dream come true.

Looking for more apps to simplify your bookkeeping? Check out our page on the year’s best accounting apps for small businesses.

At, our research is meant to offer general product and service recommendations. We don’t guarantee that our suggestions will work best for each individual or business, so consider your unique needs when choosing products and services.

1. App Store, “Shoeboxed Receipt Tracker
2. Google Play, “Shoeboxed Receipt Tracker