If you opened your accounting software this fall and found three months (or nine) of uncategorized transactions staring back at you, you have plenty of company. Most of the business owners who come to Lang Tax Solutions behind on their books aren’t careless. They got busy running the business, and the bookkeeping slid. Catch-up work follows a predictable order, though, and doing it in November instead of March gives you time to fix problems rather than file around them. Below is the same checklist we walk through with clients.
How far behind is too far to catch up before tax season?
Almost no backlog is too big to fix, as long as you can still get your bank and credit card statements. Catch-up bookkeeping simply means recording, categorizing, and reconciling every transaction you skipped so your books match what actually happened in the business. A few months of backlog is often something an organized owner can clear over several evenings. A full year, or a business with payroll and multiple accounts, usually calls for help.
The deadline that matters most comes well before April. Forms W-2 and 1099-NEC for 2026 are due to workers and the IRS by February 1, 2027, since January 31 falls on a Sunday. You can’t prepare those accurately from messy books.
Where should I start when my books are months behind?
Start with your bank statements, not the shoebox of receipts. The bank is the one record that can’t be wrong about what money moved, so it gives you a fixed point to build from.
- Write down every account the business touched this year: checking, savings, each credit card, loans, and payment apps like Square, Stripe, or PayPal.
- Find the last month you reconciled, then download statements for every month since.
- Bring the transactions into QuickBooks or whatever software you use. Bank feeds don’t always reach far enough back, so older months may need a CSV upload.
- Reconcile one month at a time, oldest first.
Reconciling means confirming that the ending balance in your books matches the ending balance on the statement. Work in order, because an error in March carries into every month after it.
Watch payment processor deposits closely. Square or Stripe deposits arrive net of fees, so a $1,000 sale might land as $970. Record the full sale as income and the $30 as a fee. Otherwise you understate revenue and lose track of a deductible expense.
What do I do with transactions I can’t remember?
Search your email and vendor accounts first. Amazon order history, Google Workspace invoices, and fuel card portals answer most mystery charges in minutes. Anything still unknown goes into a single holding account so your accountant can review it, rather than being guessed into supplies.
Personal spending on a business card is not a business expense. For a sole proprietor or single-member LLC, record it as an owner’s draw. Corporations handle it differently, so ask before you book it.
Keep the documentation that supports each deduction. The IRS generally expects you to keep those records for three years after filing, and payroll tax records for at least four.
What payroll and 1099 items does Lang Tax Solutions check first?
We start with contractor payments, because the rules changed this year. Under the One Big Beautiful Bill Act, the Form 1099-NEC threshold rose from $600 to $2,000 for payments made in 2026 (CPA Practice Advisor). Fewer contractors will need a form, but you still have to total each one’s payments to know who crosses the line. Payments you made by credit card or through PayPal are reported by the processor, not by you.
Collect a Form W-9 from any contractor you’re missing one for now, not in late January.
If you run payroll, compare your payroll reports with the wages and taxes in your books. The quarterly Form 941 totals should tie to both. A gap usually means a missed manual check or a payroll liability booked as an expense.
When should I hand my catch-up bookkeeping to a professional?
Bring in help when the backlog stretches past six months, when payroll or sales tax is involved, or when you’ve already found errors in a month you thought was closed. Those are the situations where a self-guided cleanup tends to create new problems.
At Lang Tax Solutions, catch-up work usually runs straight into tax preparation. The same team that reconciles your accounts in QuickBooks prepares the return, so nothing gets lost in a handoff. You upload statements through our client portal instead of emailing sensitive files, and we tell you plainly which questions need your input.
