4.8 on Capterra

Every Receipt. Every Deduction. Zero Paper Chase.

Upload a photo, forward an email receipt, or drop a PDF. Smart Shoebox extracts the data and matches your transactions.

Trusted by 3,000+ entrepreneurs
Cancel anytime · Built by CPAs
Smart Shoebox
Matched
Added · forwarded by email
Receipt · Staples$42.10
DateAug 12, 2026
AIMatched toOffice supplies
Receipts this month37 matched
Add a receipt →
Forward by email
Your dedicated address
Auto-matched by ReInvestWealth
The shoebox tax

Your receipts shouldn't live in an actual shoebox

Receipts in a shoebox

Paper receipts fade, disappear, and take your deductions with them.

  • Missed receipts, missed deductions.
  • No proof at audit time.
  • Write-offs you can't back up.
  • Hours lost hunting receipts.
With ReInvestWealth

Toss every receipt in the Smart Shoebox and it handles the rest.

  • Every receipt stored digitally.
  • Details extracted with AI.
  • Matched to the right transaction.
  • Audit-ready before anyone asks.
How it works

From receipt to reconciled, in three steps

Snap a photo
From your phone
Forward by email
To your Shoebox address
Drag & drop files
PDF, JPEG, or PNG

Upload, forward, or snap.

Drag a PDF, forward an email receipt, or snap a photo from your phone.

Read by AI
MerchantStaples
DateAug 12
Amount$42.10
CategoryOffice supplies

AI extracts the details.

Merchant name, date, amount, tax, and expense category are pulled automatically. No manual data entry.

Staples receipt
Mar 14
$42.10
Staples · Visa ··3307
Bank transaction
−$42.10
Matched automatically

Smart Shoebox matches it to your transaction.

Each receipt is matched to its corresponding bank transaction automatically.

Easy migration

Switch to ReInvestWealth in minutes, not weeks

Already tracking receipts somewhere else? We handle the switch from your current software.

10 minof your time required
1 dayfor most migrations
100%of your data carried over
Start Accounting For Free

Free migration with an annual plan

Reliable, growing finances illustration
Pricing

One Price. One Plan.

Get Started For Free

30 days free · Cancel anytime

$28 USD/mo

One plan. One tier.

  • Unlimited Bank Connections
  • Unlimited Currencies
  • Unlimited Receipt Uploads
  • AI Bookkeeper (Trained by CPAs)
  • Unlimited Invoicing (Stripe)
  • Real-Time Financial Reports
  • Automatic Receipt Matching
  • Email Receipt Forwarding
  • Custom Automation Rules
  • Project & Client Tags
  • Bank Statement Uploads
  • Invite Your Accountant
  • Full Audit Trail
  • Accountant-Ready Exports
  • Free Done-for-You Migration
Trusted by growing businesses

Loved by founders, backed by CPAs

ReInvestWealth 5-star reviews on Capterra, Software Advice and GetApp
FAQ

Questions, answered

How do I forward receipts to Smart Shoebox?

Each ReInvestWealth account gets a unique forwarding email address. Go to Smart Shoebox → Email Setup to find yours. Forward any receipt email to that address, from Gmail, Outlook, vendor confirmation emails, or any online purchase, and it appears in Smart Shoebox within minutes.

Does Smart Shoebox match receipts to bank transactions automatically?

Yes. Smart Shoebox compares the receipt's date, merchant, and amount with your bank transactions and links each match automatically, going back as far as it needs. You can also link receipts manually from the receipt list, which shows what's matched and what's still unmatched so you find the gaps before filing, not after.

What file types does Smart Shoebox accept?

JPEG, PNG, and PDF. Most receipt photos taken on a phone camera work without any conversion needed. Email-forwarded receipts are extracted directly from the email body or attached file.

What details does the AI read from each receipt?

The merchant, date, amount, currency, taxes, and tip, with no typing on your end. Open any receipt to see the extracted details next to the original file, and edit them if anything needs correcting.

Why didn't my forwarded receipt show up?

The most common reason is the sending address: only senders on your allowed list are accepted, so add the email address you forward from in your Smart Shoebox settings. Also check the file, since each email can carry one attachment (PDF, JPEG, or PNG, up to 10 MB). When something is rejected, an error email explaining why goes back to the sender.

Does the IRS accept digital copies of receipts?

Yes. The IRS has accepted electronic records since Revenue Procedure 97-22, as long as they're accurate and retrievable. Smart Shoebox keeps the original image together with the extracted details, so every receipt stays available on demand.

Never lose a receipt again.

Start free, snap or forward your first receipt, and let ReInvestWealth read it and match it for you.