Frequently Asked Questions

Everything you need to know about Shorestack Books

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General

What is Shorestack Books?

Shorestack Books is a desktop bookkeeping app for Mac, built for freelancers, small businesses, and agencies. It handles bank imports, auto-categorization, double-entry accounting, invoicing, and tax reporting — all in a signed, notarized macOS app you buy once and own.

Who is Shorestack Books for?

It's built for freelancers and consultants who need to track income and expenses, small businesses looking for an affordable bookkeeping tool, small agencies managing vendors and invoices, and rental property owners who need Schedule E reporting.

Do I need any accounting knowledge to use it?

No. Shorestack Books starts in Essential view, which shows only the features most people need: import transactions, review and categorize, view your P&L. The app handles double-entry accounting behind the scenes. Switch to Pro view anytime to access the Chart of Accounts, journal entries, and advanced reports — every feature is included with every license.

Does it work offline?

Yes — the app is fully offline-first. Your company file is a local SQLite database on your Mac, so you can use every feature (imports, categorization, reports, invoicing, exports) with no internet connection. Live bank feeds via Plaid do require internet, but manual CSV/OFX imports always work offline.

What macOS versions are supported?

The app runs on macOS 13 (Ventura) and later, on both Apple Silicon and Intel Macs. It's signed with an Apple Developer ID and notarized, so it launches without Gatekeeper warnings. Compatibility patches ship within one week of any breaking macOS release.

Bank Connections & Imports

How does the bank connection work?

Shorestack Books uses Plaid, the same service used by Venmo, Robinhood, and thousands of other financial apps. When you connect a bank, Plaid opens a secure window where you log into your bank directly. Your bank credentials are never shared with Shorestack — Plaid handles the authentication and sends us only your transaction data.

Which banks are supported?

Plaid connects to 12,000+ financial institutions in the US, including Chase, Wells Fargo, Bank of America, Capital One, US Bank, Citi, and most credit unions and community banks. If your bank supports online banking, it almost certainly works with Plaid.

Is connecting my bank safe?

Yes. Plaid is trusted by millions of users and thousands of apps. Your bank login happens inside Plaid's secure window — Shorestack never sees your username or password. Plaid uses bank-level encryption (AES-256) and is SOC 2 Type II certified. The connection is read-only: Plaid can only read transactions, it cannot move money or make changes to your account.

What data does Plaid share with Shorestack?

Only transaction data: date, description, amount, and Plaid's category suggestion. We do not receive your bank login credentials, account numbers, routing numbers, or any other sensitive banking details.

Can I disconnect my bank at any time?

Yes. Go to the Banking tab and click Disconnect on any connected account. This immediately revokes the Plaid access token. Transactions already imported will remain in your books, but no new transactions will sync.

What if I don't want to connect my bank?

No problem. You can import transactions manually using CSV, Excel, OFX, or QFX files downloaded from your bank's website. Shorestack auto-detects column mapping for most banks, including Bank of America, Chase, and generic CSV formats.

How often do transactions sync?

When you open the Banking tab, Shorestack checks for new transactions from your connected banks. You can also manually trigger a sync at any time. New transactions appear in the Review tab for you to categorize and approve before they hit your books.

Does Plaid work with business bank accounts?

Yes. Plaid supports both personal and business checking accounts, savings accounts, and credit cards. If your bank supports it through online banking, it should connect through Plaid.

Is the live bank feed a permanent feature?

Live bank feeds rely on Plaid's ongoing service, so the supported integration may evolve over time as we update how it works. Manual CSV and OFX imports are a permanent part of the app — every major bank lets you download these files from online banking, and they work forever on any version of Shorestack Books you've installed.

Pricing & Licenses

How much does it cost?

Shorestack Books is a one-time purchase priced by the number of users you need:

Solo — $79 · 1 user, all features included.
Team — $199 · up to 3 users, all features included.
Agency — $299 · up to 5 users, all features included.

Every license includes every feature. There's no feature-gating by tier — you're only paying for seats.

Is this a subscription?

No. You pay once and own the version you bought. There are no monthly or annual fees, no forced renewals, and no features that disappear if you stop paying. The app keeps working on the version you installed, for as long as you want to use it.

Will I have to buy a new version every year?

No. Bug fixes, macOS compatibility patches, and minor improvements ship as free updates to the version you own. When a major new release comes along, we'll offer it as an optional paid upgrade — buy it if the new capabilities are useful to you, skip it if your current version still works. There's no cadence we force on you.

Can I transfer my license to a new Mac?

Yes. Your license is tied to your account, not a specific machine. Deactivate it on the old Mac from the in-app account portal, then activate it on the new Mac — no fee, no support ticket required. Multi-user licenses work the same way: move any seat between any Macs you own at any time.

What if I'm not happy with it?

Every purchase is covered by a 30-day money-back guarantee. If Shorestack Books isn't the right fit, reply to your receipt email or write to contact@shorestack.io within 30 days and we'll refund you — no questions asked, typically processed within two business days.

Do I need a separate OpenAI key for receipt scanning?

Yes — receipt scanning uses OpenAI for OCR, and you supply your own API key (BYOK) in Settings → API Key. You pay OpenAI directly for each scan (typically a fraction of a cent) and your key is stored locally on your Mac, never on our servers. If you don't want to set up an OpenAI key, you can always add receipts by hand.

Features

What is the difference between Essential and Pro view?

Essential view shows a simplified set of tabs: Dashboard, Banking, Import, Review, Transactions, Invoicing, P&L, Balance Sheet, Reconciliation, and Settings. This covers everything most small business owners need.

Pro view exposes additional tabs: Chart of Accounts, Journal Entries, General Ledger, Trial Balance, Budget, Cash Flow, Audit Trail, and more. The toggle lives in the sidebar — every feature is included with every license, so switching views is just a UI density preference, never an upgrade.

How does auto-categorization work?

Shorestack uses a 4-layer categorization engine. When a transaction comes in, it checks: (1) your custom rules (e.g., “Amazon = Supplies”), (2) learned patterns from your past approvals, (3) smart matching based on vendor name similarity, and (4) Plaid's category hint. Most transactions get categorized automatically after a few weeks of use.

Can I send invoices to customers?

Yes. The Invoicing tab lets you create professional invoices with line items, payment terms (Net 30, Net 15, etc.), and PDF export. You can track payment status, see aging reports, and record full or partial payments.

Does it support double-entry accounting?

Yes. Every approved transaction automatically generates a balanced journal entry (debits = credits). This is GAAP-compliant and happens behind the scenes — you don't need to understand debits and credits unless you want to. All reports are generated from journal entries for accuracy.

What is Sandy?

Sandy is the built-in expert bookkeeping assistant. It provides 200+ plain-English answers to common bookkeeping questions, a glossary of accounting terms, contextual tips based on which tab you're on, and guided actions that can navigate you to the right place in the app. Sandy runs entirely offline with zero API costs — it's not an AI chatbot, it's a structured knowledge base.

How does receipt scanning work?

Upload or photograph a receipt, and Shorestack's OCR engine extracts the vendor name, date, amount, and category. It creates a draft transaction that you review and approve. Batch scanning lets you upload multiple receipts at once. Receipt scanning uses your own OpenAI API key (BYOK), so there's no per-month scan quota — you pay OpenAI directly for what you use, typically a fraction of a cent per receipt.

How does the OpenAI API key (BYOK) work?

In Settings → API Key (BYOK), you enter your own OpenAI API key. Your key is stored locally on your Mac only — it's never sent to or stored on our servers. Standard OpenAI API usage charges apply, billed by OpenAI to your own account. You can test, save, or remove your key at any time. Get an API key at platform.openai.com/api-keys.

Can I manage multiple businesses?

Yes — unlimited businesses on every license. Each business is its own company file with its own transactions, bank accounts, and reports. Use the Company Manager in the File menu to open, switch between, or create new company files. Consolidated reports let you roll up combined P&L and Balance Sheet across businesses.

Security & Privacy

Where is my data stored?

Your data lives in a local SQLite company file on your Mac, stored wherever you choose to save it (Documents, iCloud Drive, Dropbox, an external drive — your call). Nothing is uploaded by default. You own the file outright and can copy, move, or back it up like any other document.

Does any of my data go to the cloud?

Only if you turn it on. Optional cloud sync is available if you want your company file mirrored for backup or access across multiple Macs — off by default, controlled entirely from Settings. Bank imports through Plaid and receipt OCR through your OpenAI key are separate internet-using features that only call out when you use them.

Is my data encrypted?

Local backups can be encrypted with AES-256-GCM — the same standard used by banks and government agencies. Enable backup encryption in Settings and pick your own passphrase. Cloud sync, if you opt into it, is encrypted in transit (TLS) and at rest.

Do you sell my data?

No. Shorestack does not sell, share, or monetize your financial data in any way. Since your data lives locally on your Mac, we don't see it in the first place unless you explicitly enable cloud sync. See our Privacy Policy for full details.

Can I back up my data?

Yes. The File menu → Backup command (⌘B) copies your company file to a location you choose. Scheduled automatic backups are available in Settings, with optional AES-256 encryption and up to 10 rolling copies. Since the file is just a regular SQLite database, you can also back it up through Time Machine, iCloud, or any other backup tool you already trust.

Tax & Reports

What reports are available?

Every license includes the full report suite: P&L, Balance Sheet, General Ledger, Trial Balance, Cash Flow Statement, Budget vs. Actual, Consolidated Reports, and all tax reports. Every report can be exported as a PDF or emailed directly to your accountant.

Does it generate Schedule C or Schedule E?

Yes. Schedule C is auto-generated for sole proprietors, mapping your expense categories to IRS line items. Schedule E covers rental property income and expenses. Both ship with every license.

Can I generate 1099s for my contractors?

Yes. The Tax Handoff tab generates IRS-formatted 1099-NEC PDFs (Copy A, B, and C) and FIRE e-file format for electronic filing. You can track filing status, send recipient copies, and batch-generate for all qualifying vendors.

Does it calculate estimated quarterly taxes?

Yes. The Estimated Taxes tab uses the IRS Form 1040-ES formula, including self-employment tax, federal income tax with current brackets, and safe harbor analysis. It shows quarterly payment amounts and due dates.

Can I email reports to my accountant?

Yes. Email Reports lets you select any report, choose a date range, add recipients, include a message, and send the report as a PDF attachment — all from within the app. Included on every license.

Getting Started

How do I get started?

Buy a license from shorestack.io/books, receive your license key and download link by email within minutes, then install the signed & notarized .dmg on your Mac. On first launch, enter your license key and the onboarding wizard walks you through creating your first company file, naming your business, and choosing Essential or Pro view.

How do I import my existing transactions?

Go to the Import tab and upload a file from your bank. Shorestack supports CSV, Excel (.xlsx), OFX, and QFX formats. The import wizard auto-detects your bank format and maps columns automatically. After import, transactions appear in the Review tab for categorization.

How do I connect my bank?

Go to the Banking tab and click Connect Bank. This opens a Plaid window where you search for your bank and log in securely. Once connected, transactions sync automatically on demand. Live bank feeds are included with every license — no additional fee.

Can I migrate from QuickBooks?

Yes. The in-app Migration Wizard accepts the standard CSV exports from QuickBooks — Chart of Accounts, Trial Balance, Balance Sheet, and Profit & Loss — and builds out your opening books so you can pick up where you left off. You can also bring in transaction history via generic CSV import and let the categorization engine learn your patterns as you review.

Customization

Can Shorestack Books be customized for my industry?

Yes. For businesses with workflows that aren't covered by the stock app, we offer custom builds as a separate professional services engagement — industry-specific modules, tailored expense categories and reports, custom workflows, and dedicated onboarding. A bar's pour-cost tracking is very different from a candle shop's production costing, and we can build for either.

What kind of customizations can you build?

Examples include: bar/restaurant pour-cost tracking and daily register reconciliation, e-commerce marketplace fee breakdowns and per-SKU COGS, agencies project-based P&L and retainer billing, retail raw material costing and batch production tracking, property management tenant ledgers and maintenance costing, and trades job costing and estimate-to-actual comparisons. If you can describe the workflow, we can likely build it.

How much does a custom build cost?

Custom pricing depends on scope. After a discovery call we deliver a fixed-price proposal so you know the full cost up front — typically a one-time build fee plus an optional ongoing retainer for maintenance, depending on the complexity of what we're building.

How long does a custom build take?

Most custom builds ship within 2–4 weeks from approval. Larger projects with multiple custom modules may take 4–8 weeks. We'll provide a timeline estimate in our proposal.

How do I start a custom build?

Visit the Customization page and fill out the consultation request form. Tell us about your business, your industry, and what you need. We'll respond within 1–2 business days to schedule a discovery call.

Troubleshooting

My bank connection stopped syncing. What should I do?

Bank connections can occasionally require re-authentication, especially after password changes or if your bank updates their security. Go to the Banking tab and look for a status indicator on the affected connection. Click to re-authenticate through Plaid. If the issue persists, disconnect and reconnect the account.

I see duplicate transactions. How do I fix this?

Shorestack has built-in 2-pass duplicate detection that catches most duplicates during import. If some slip through, go to the Maintenance tab and run the data integrity scanner — it will flag potential duplicates for your review. You can void duplicates (which preserves the audit trail) rather than deleting them.

Can I undo a mistake?

Shorestack uses a void-instead-of-delete approach. When you void a transaction, it creates a reversal journal entry and marks the original as voided — nothing is ever permanently deleted. This gives you a complete audit trail. Year-end closings can also be reversed if needed.

The app won't launch or looks broken. What should I try?

First, fully quit the app (⌘Q) and relaunch. If the issue persists, make sure you're on a supported macOS version (13 Ventura or later) and that the app is up to date — Shorestack Books → Check for Updates in the menu bar. Your data is safe either way: your company file is a regular SQLite file on disk, independent of the app binary. If you're still having trouble, email contact@shorestack.io with a screenshot and we'll jump in.

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