Shoeboxed

Shoeboxed occupies a unique niche in the expense management space by focusing on the specific problem that plagues small business owners and freelancers: turning a pile of physical receipts into organized, tax-ready digital records. Our evaluation confirms it does this particular job exceptionally well, with the combination of AI-powered OCR and human verification delivering accuracy rates that pure-software solutions cannot match. The Magic Envelope service is the signature feature that no competitor replicates. You literally mail your physical receipts to Shoeboxed in prepaid envelopes, and they scan, categorize, and digitize everything. This is perfect for people who accumulate physical receipts from business travel, client meals, and in-store purchases but never get around to scanning them. The turnaround is typically 5-10 business days, which is acceptable for ongoing expense tracking though not suitable for real-time reporting. The mobile app scanning works well for day-to-day receipt capture, with human verification catching errors that OCR-only apps miss. IRS acceptance of Shoeboxed records is a meaningful differentiator, as it provides genuine peace of mind during audits. The export to QuickBooks, Xero, and Wave makes tax preparation significantly easier by providing clean, categorized expense data ready for accounting software. The Startup plan at $24/month (billed annually) includes 50 document scans per month with unlimited storage. The Professional plan at $40/month increases to 150 scans and adds the Magic Envelope service. The Business plan at $60/month provides 350 scans and unlimited users. All plans include human-verified data extraction and IRS-accepted records. The limitations are clear. Shoeboxed is not a corporate expense management system with approval workflows, policy enforcement, or corporate card management. Real-time expense tracking is not its strength due to human verification processing time. And at high receipt volumes, pure-OCR alternatives like Dext or Expensify may be more cost-effective despite lower accuracy. We recommend Shoeboxed for self-employed individuals, freelancers, and small business owners who need reliable receipt-to-digital conversion with tax-compliance guarantees. The Magic Envelope service makes it uniquely valuable for anyone drowning in paper receipts.