Month-end bookkeeping prep: categorize transactions and chase missing receipts

Month-end for most small businesses means a spreadsheet of transactions, a shoebox (or inbox) of receipts, and a lot of “what was this charge again?” This workflow doesn’t replace your bookkeeper or your accounting software. It gets everything ready for them in a fraction of the time.

What you’ll end up with

1. A categorized transaction list with a suggested category for every line, plus a confidence level.
2. A “needs you” list of transactions the AI couldn’t categorize with confidence.
3. A missing-receipts list matched against the receipts you have.
4. Chase email drafts to vendors for missing invoices or receipts.
5. A short summary of the month: totals by category, and anything unusual.

Step 1: Make a category list (15 minutes, once)

Use the same categories as your accounting software or your bookkeeper’s chart of accounts. Ask your bookkeeper for the list if you don’t have one. Then add the rules you already know:

CATEGORIES: Advertising, Bank fees, Contractors, Equipment, Insurance,
Meals (client), Office supplies, Rent, Software, Travel, Utilities,
Cost of goods, Owner draw, Transfer (not an expense)

KNOWN VENDORS:
- "SQ *" prefix = card processor fees -> Bank fees
- Google Workspace, Adobe, Canva -> Software
- [Your landlord's name] -> Rent
- Transfers between my own accounts -> Transfer

Save it as categories in a Project.

Step 2: Set up the instructions (15 minutes)

You help a small business owner prepare month-end bookkeeping for their
bookkeeper. You suggest; the owner and bookkeeper decide. You do not give
tax advice.

Inputs each month:
- TRANSACTIONS: a CSV export from the bank/card
- RECEIPTS: a list of receipt file names or a folder listing
  (e.g. "2026-09-03_staples_42.18.pdf")

Output:

1. CATEGORIZED LIST: Date | Description | Amount | Suggested category |
   Confidence (High/Medium/Low) | Reason (one short phrase).
   Use only categories from "categories". Apply its vendor rules first.

2. NEEDS YOU: every Low-confidence line, with the question you'd ask the
   owner ("Amazon $214.50: office supplies or equipment?").

3. MISSING RECEIPTS: expense lines over $[25] with no matching receipt
   (match on date ±3 days and amount). Include vendor and amount.

4. CHASE DRAFTS: for missing receipts from vendors who normally email
   invoices, a short polite email requesting a copy. Leave [CHECK] where
   an account number or order number is needed.

5. MONTH SUMMARY: total by category, and 3–5 bullets on anything unusual
   compared with a typical month (big one-offs, new vendors, duplicates).

Never change amounts or dates. Flag anything that looks like a duplicate
charge.

Step 3: Name receipts consistently (ongoing, a small habit)

Matching works best when receipt files follow one pattern: date_vendor_amount.pdf. If you take receipt photos with your phone, rename them when you save them. It’s the single biggest time saver in this whole workflow.

Step 4: Run it monthly (5 minutes)

On the first of the month, download last month’s transactions as CSV, open a new chat in the Project, upload the CSV and the receipts folder listing, and send:

September transactions and receipts attached. Run month-end prep.

Step 5: Review, chase, hand off (30–40 minutes)

• Answer Needs You. Reply in the chat (“Amazon $214.50 was a monitor, so Equipment”) and ask for an updated list.
• Scan the High-confidence lines. Don’t skip them. It’s quick, and it’s where silent mistakes hide.
• Check duplicates it flagged against your bank statement.
• Send the chase emails after filling the [CHECK] gaps.
• Send the final list and receipts to your bookkeeper, or import them into your accounting software.

Tips

• Remove account numbers from the CSV before uploading. You only need date, description, and amount. See PII.
• Update categories every month with new vendor rules from your Needs You answers. By month three, most lines come back High confidence.
• Pair this with morning inbox triage and put invoices in their own section, so receipts are easy to find at month-end.