Open Arsenal

Your Health Savings, Optimized.

Shoebox+ is an open-source AI-powered platform designed to help users maximize the long-term value of their Health Savings Accounts (HSAs). Instead of treating an HSA like a simple debit account for medical expenses, Shoebox+ reframes it as a tax-optimized investment and reimbursement system. It combines receipt tracking, tax rule interpretation, investment strategy modeling, and financial institution analysis into a single intelligent workflow that continuously adapts to the user’s financial situation and changing IRS regulations.

At its core, Shoebox+ enables what is commonly referred to as the “shoebox strategy,” where users pay for medical expenses out-of-pocket, securely store receipts, and reimburse themselves later from their HSA. The platform automates this process by uploading and archiving receipts, extracting structured data through OCR, and maintaining a searchable reimbursement ledger. This allows users to preserve their HSA funds for decades of tax-free investment growth while maintaining full compliance and audit-ready records.

Beyond receipt management, Shoebox+ includes advanced financial optimization features such as contribution planning, portfolio simulation, and risk modeling. The system can analyze user income, tax bracket, and employer contributions to recommend optimal HSA funding strategies, while also simulating long-term investment outcomes under different market conditions. It further extends into financial institution optimization, comparing HSA providers based on fees, investment options, and account features to recommend the most efficient platforms for each user’s strategy.

Shoebox+ also incorporates an IRS compliance intelligence layer that tracks changes in federal and state tax rules affecting HSAs. When relevant updates occur, the system can reassess user strategies and suggest adjustments to contributions, reimbursements, or account structure. Combined with employer benefits optimization and community-driven insights, Shoebox+ acts as a continuously evolving financial assistant focused specifically on maximizing the tax and investment advantages of Health Savings Accounts.