Every Receipt. Every Deduction. Zero Paper Chase.
Upload a photo, forward an email receipt, or drop a PDF. Smart Shoebox (your receipt inbox) extracts the data and matches it to your bank transactions automatically.
We work with the best in the business
Your receipts shouldn't live in an actual shoebox
- •A missed receipt means a missed deduction
- •At audit time, “I think I paid for that” isn't a defence
- •A missing receipt is a missing write-off you can't back up
- •The average small business owner spends hours per year hunting down receipts they know they have somewhere
- ✓Smart Shoebox stores everything digitally
- ✓Extracts the details with AI
- ✓Matches each receipt to the right transaction
- ✓Your books are audit-ready before anyone asks
From receipt to reconciled, in three steps
Upload, forward, or snap.
Drag a PDF, forward an email receipt to your unique Smart Shoebox address, or upload a photo from your phone. Works from Gmail, Outlook, vendor confirmation emails, and any online purchase.
AI extracts the details.
Merchant name, date, amount, tax, and expense category are pulled automatically. No manual data entry.
Smart Shoebox matches it to your transaction.
Each receipt is matched to its corresponding bank transaction. View what's matched and what's still unmatched — so you find the gaps before filing, not after.
Receipt capture that's actually effortless
Centralized digital receipt storage
No physical filing cabinet, no hunting through old emails.
Email forwarding works from any email client
Gmail, Outlook, vendor confirmations, online purchases.
AI extracts the details automatically
AI extracts merchant, date, totals, and tax automatically.
Filter by matched / unmatched
Filter by matched / unmatched to find gaps before filing.
An audit-ready paper trail
Receipts matched to transactions create an audit-ready paper trail. Reduces missed deductions from lost or forgotten receipts.
Less paper chasing. More peace of mind.
Capture a receipt in seconds and let the AI file it where it belongs.
Start your free 30-day trial →Switch to ReInvestWealth in minutes, not weeks
Already tracking receipts somewhere else? We do the heavy lifting. Most migrations take about 10 minutes of your time and are done within a day, with your historical data fully intact.
- Free migration with an annual plan
- We handle the switch from your current software
- About 10 minutes of work on your end
- Most migrations completed in under a day
- Historical data stays intact
Loved by founders, backed by CPAs
Amazing Software Backed by an Incredible Team
It's clear that the software was created by a team passionate about helping businesses succeed. They go above and beyond to provide support, which adds tremendous value to an already excellent product.
Made my life so much easier so I absolutely recommend
Best Smart Accounting app for Canadian Entrepreneurs
Just awesome. With limited smart bookkeeping options available in Canada, it helps reduce the time and cost of handling repetitive tasks.
Effortless tax filings
My experience with them has been great. They're very responsive and helpful. The platform is continuously evolving and improving.
ReInvestWealth expedites the process
Highly recommend, it's helping my business
ReInvestWealth is a game changer
It's been really good.
It's been really good. It works a lot like QuickBooks but at a fraction of the price. Definitely give this system a go.
Really easy to use and save SOOOO much time!
Easy to use and AI features save a lot of time. Love the easy integration! The team are super responsive as well.
One Price. One Plan.
Simple pricing for everything ReInvestWealth does
- AI bookkeeping
- Unlimited bank connections
- Receipts & invoicing
- GST/HST e-filing
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 — it appears in Smart Shoebox within minutes.
Does Smart Shoebox match receipts to bank transactions automatically?
Yes, for transactions within 35 days of the receipt date. Smart Shoebox matches based on merchant name and amount. After 35 days, auto-matching stops — you can still link receipts manually from the receipt list.
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.
Keep reading
Never lose a receipt again.
Start free, snap or forward your first receipt, and let ReInvestWealth read it and match it for you.