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substackMoney & Bills

Annotate invoice PDFs using last year's expense codes

At a glance

Brosnan Hoban used Claude to label invoices from prior examples and reconcile the paperwork against bank statements before accountant handoff. This workflow is listed under Money & Bills, Document Organization, Expense Records.

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What they did

1) Collect copies of previously coded invoice sheets, this year's invoice PDFs, and matching bank statements. Remove account numbers and other details unnecessary for the task. Start with a small batch in Claude with file upload and PDF-output capability. 2) Upload the prior-year examples and current invoices. Ask Claude to match expenses to the existing codes and descriptions and write both directly onto returned PDF copies. Require it to flag unmatched items. 3) Supply relevant bank-statement entries for unfamiliar expenses, then ask it to compare every debit with the invoice paperwork and identify missing sheets by transaction and date. 4) Check the matches, amounts, and PDF annotations yourself, resolve the exception list, and give the organized records to your accountant.

How it went

Claude returned annotated PDFs and identified a statement transaction with no matching invoice sheet.

Worth knowing

The author used his accountant's established coding examples; his accountant still handles the tax work.

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Prompt excerpt

No prompt excerpt was provided by the source.

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