Bookkeeping and payroll for small businesses across central Virginia.

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Will I get in trouble with the IRS for falling behind on my books?

The IRS doesn’t regulate your bookkeeping. They regulate your tax compliance. Falling behind on reconciling your accounts or categorizing transactions isn’t something that triggers IRS penalties on its own. Nobody from the federal government is checking whether your QuickBooks file is current.

The problem is what happens downstream. When your books are a mess, you can’t file accurate tax returns. You might underreport income because you lost track of cash deposits. You might miss deductions because you didn’t record expenses properly. You might file late because you’re scrambling to reconstruct a year’s worth of transactions in April.

Those downstream consequences are where real trouble starts. Late filing penalties run 5% of unpaid taxes per month, up to 25%. Late payment penalties add another 0.5% per month. If you underreport income significantly, accuracy penalties can hit 20% of the underpayment. And if the IRS decides your return looks suspicious enough to audit, messy books make it much harder to defend the deductions you claimed.

Being behind also means you might be overpaying taxes without realizing it. If you’re not tracking expenses properly, you’re probably missing legitimate deductions. The IRS won’t send you a refund for deductions you forgot to take.

The good news is that getting caught up fixes the problem. Catch-up bookkeeping is exactly what it sounds like. You reconstruct the missing months, get everything reconciled, and move forward with accurate records. It’s more work than staying current would have been, but it’s not impossible.

If you’re worried about being behind, the best thing you can do is address it now rather than waiting. A Richmond bookkeeper who works with small businesses sees this constantly. You’re not the first person to fall behind, and cleaning things up before tax season is always easier than explaining discrepancies to an auditor later.

The IRS cares about what you file, not how you got there. Get your books straight, file accurate returns, and you’ll have nothing to worry about.

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More Questions

What documents do I need to provide for catch-up bookkeeping?

Bank statements are the foundation. Credit card statements come next. Receipts, invoices, and payroll records help fill in the details, but you don't need perfect documentation to get started.

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How Do I Set Up QuickBooks for the First Time?

Start with the right version, build a chart of accounts that matches your business, connect your banks correctly, and set up a few rules. Get these basics right and QuickBooks actually works. Get them wrong and you'll spend years fixing mistakes.

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How do I know if my books are a mess?

There are clear warning signs: bank accounts that don't reconcile, surprise tax bills, financial statements that don't match reality, and transactions piling up uncategorized. If you're avoiding your books, that's usually confirmation enough.

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Which QuickBooks plan is right for my small business?

The right plan depends on user count, inventory needs, and whether you track project costs. Most small businesses do fine with Simple Start or Essentials. Plus is worth it only if you manage inventory or need job-level profitability.

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What's the best way to handle cash management in a restaurant?

Start with consistent register banks and count cash at every shift change. Reconcile to your POS daily, deposit frequently, and limit who handles cash to create clear accountability.

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What's the best way to track business expenses?

The best expense tracking system is one you'll actually use consistently. Separate business and personal finances, capture receipts immediately, and reconcile weekly instead of waiting until month-end.

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Virginia bookkeeping firm focused on small businesses. Bookkeeping, payroll, and fractional CFO services from a local Richmond team. A decade of working with businesses like yours. QuickBooks ProAdvisor certified.

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