How-to · Bookkeeping catch-up

How to catch up on a year of bookkeeping yourself

You haven't kept the books all year, and now you need them. This is the order that works: collect every statement, make sure none is missing, take out the money that only moved between your own accounts, sort what's left into business and personal, then export. Pennyrow does the checking in your browser, so your statements never leave your device.

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What you need

A statement for every month of the year, for every account the business touched: checking, savings, business cards, and any personal card you also used for business purchases.
PDF statements made by your bank, or CSV, OFX or QFX downloads. A zip of them works too. Scans and photos can't be read, so download the PDF your bank made instead.
Your bank's website. The guides by bank say where each bank keeps its statements and how far back they go.

Step 1: download everything first

Get all twelve statements for each account before you start, so you can see the gaps in one go. PDF statements are the better file for catching up, because they print an opening and a closing balance, and that is what lets Pennyrow usually check that each month adds up. Most CSV and OFX downloads have no balances, so they show “No balances to check”. Their rows are still read.

Step 2: add them all at once

Open Pennyrow, choose your files or drag them in. A whole year at once is fine, and you can mix banks and cards.
Each statement is read on your device and gets a badge: “✓ Balanced”, “Row 12 is off by $40.00”, or “– No balances to check”.
Work through the tabs in order: Statements, Catch-up, Categorize, Summary, Export.

A “✓ Balanced” badge means the totals add up. It does not prove that every row was read correctly, so compare with your original statement.

Step 3: fix what the Catch-up tab finds

The Catch-up tab looks across every file for the year. Each line below is something it can tell you.

A statement that doesn't balance. It shows the first row that is off and by how much. Open the statement and compare that row with the original.
A missing month. A month with no statement for an account is listed, for example “April 2025 is missing for Checking ••4821”. Download it and add it.
A balance-chain break. When one statement's closing balance doesn't match the next one's opening balance, a statement between them is probably missing.
Transfers and card payments. Money moving between your own accounts, including a card payment from checking, is matched and kept out of income and spending. Matching needs both sides, so add the card and the account that paid it. A payment whose other side isn't in your files is listed under “Possible transfers to check” and left out until you decide; “Not a transfer” puts it back.
Duplicates removed. The same transaction in two overlapping files of the same account is counted once, and each removal is listed. Identical rows inside a single file are kept, because two $5 coffees on one day are real. How overlapping files are handled.
Which accounts are business? Set each account to Business, Personal or Both. Rows in a business account count in the profit and loss; in a Both account you choose merchant by merchant.

Step 4: confirm categories

The Categorize tab lists each merchant once, with how many rows and how much money. Pennyrow suggests a Schedule C (Form 1040) line, and you confirm or change it with the Confirm button. There is no confirm-all, so nothing is applied that you didn't choose. A merchant it can't place stays as “Uncategorized: ask your preparer”. Your choice applies to every row from that merchant. More on Schedule C categories.

Step 5: read the summary and export

The Summary tab totals the year: income and expenses by line, what is still uncategorized, and the money that isn't part of profit (transfers, card payments, loan and tax payments, owner draws). The Export tab makes Excel (.xlsx), CSV, OFX, a QuickBooks® Online bank CSV and a QuickBooks Desktop .iif file. The files cover one year at a time. Using the file in Google Sheets.

Twelve files, one list

The Excel file opens on a Transactions sheet with every row from every account. After it come a Summary, one sheet per account, Categories and Checks. The CSV is the Transactions list on its own. Its columns are Date, Account, Description, Money in, Money out, Balance, Business/Personal, Category, Schedule C line, Category status, Suggestion, Transfer, Source file and Source row. Dates are written year-month-day and money is plain numbers, so both sort correctly. Money in and Money out are separate columns, and both are positive numbers. Source file and Source row point back to the exact line in the statement you added, so any number can be traced to where it came from.

Choose Excel if you want the Summary, one sheet per account, Categories and Checks along with the list. Choose CSV if you only want the list, for example to load into another tool.

How overlapping files are handled

Overlap is the usual problem when you combine files: a monthly statement and an activity download both cover July, or two downloads cover the same weeks. Pennyrow handles it like this.

It compares rows only across different files of the same account. A row in two files with the same date, the same amount and the same merchant text is counted once.
A purchase can carry its purchase date in one file and its posting date, a day or three later, in the other. Rows with the same amount and merchant up to four days apart are matched too, but only when both fall inside the dates the other file covers, so two real purchases in back-to-back months are not merged by this rule.
Identical rows inside one file are kept. Two $5 coffees on one day are two purchases.
The copy that is kept comes from a statement that balanced, where there is one.
Every removal is listed on Catch-up under “Duplicates removed”, with both file names.

Some downloads don't say which account they belong to, so two files from the same account can look like two accounts. When they share rows, Pennyrow asks: “look like the same account: 6 rows have the same date and amount. If they are, count them as one so those rows aren't counted twice.” Choose “Count as one account”, or “They're different accounts” if they are.

Limits

The Export tab makes files for one year at a time. If your statements cross a year end, the page says so and offers “Excel, all dates” and “CSV, all dates” to download every row. Each file can be up to 30 MB, and a zip of statements up to 200 MB. Scans and photos can't be read. A password-protected PDF asks for its password, which is used only to open that file in your browser tab and is never saved. Rows whose date or amount can't be read are skipped, and Pennyrow tells you how many.

What the checks flagged in the built-in sample

Choose “Try it with sample statements” on the Pennyrow page and you will see these same numbers. The sample is made up: a checking account, a savings account and a credit card for a small business, with 28 monthly files for 2025. The checking account comes from 12 files: monthly statements plus one activity download that overlaps July.

Check	Result
Statements read	28
Rows in 2025	300 across 3 accounts
Statements that balance	28 of 28
Months missing a statement	1 (April 2025, Checking ••4821)
Duplicates removed	13 (rows in both a monthly statement and an activity download)
Transfers and card payments matched	15 (4 transfers, 11 card payments)
Possible transfers to check	2
Merchants to confirm	24

One of the 13 duplicates reads:

Jul 12, 2025 · MARSHWICK ELECTRIC CO · -$90.46 is in both MapleRidgeBank_x4821_checking_2025-07.csv and MapleRidgeBank_x4821_activity.csv; kept the one from MapleRidgeBank_x4821_checking_2025-07.csv

Account	Files	Rows
Checking ••4821	12	130
Savings ••7731	4	16
Card ••9876	12	154
Combined	28	300

All 28 files end up as one list of 300 rows for 2025. Before reading a single row you know which statement to go and get, which two payments to look at, and which 24 merchants need a category.

Questions

How many statements do I need to catch up a year?

One for every month of the year, for every account you used for the business. The Catch-up tab names any month that has none.

Can I stop halfway and come back?

Your statements stay in the tab's memory, and closing or reloading the tab clears them. Save my work makes one file with your statements as Pennyrow read them, your row fixes and your settings. Your browser saves it like any other download and it is never sent to us. Open it next time to pick up where you left off.

What if my bank won't give me an old statement?

The Catch-up tab keeps listing that month as missing, because Pennyrow doesn't make up rows. Ask the bank for a copy. The guides by bank say how far back each one keeps statements.

Can I combine PDF and CSV statements from the same bank?

Yes. Pennyrow reads each file by its own layout and combines them, and a row that appears in both files of the same account is counted once. Most CSV downloads have no balances, so the balance check applies to the files that have them.

Why is my combined total lower than the sum of my statements?

Rows in two overlapping files are counted once, and money moving between your own accounts is matched and kept out of income and spending. Both are listed on the Catch-up tab so you can see each one.

Does this connect to my bank account?

No. You download the statements yourself and Pennyrow never asks for a bank login. How to check that yourself.

Is this tax advice?

No. Pennyrow organizes your own statements and totals them. Line references and suggested categories are for organizing, and your return preparer decides what goes on a return.

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