AI Bookkeeping: I Tested AI on Uncategorized Bookkeeping Transactions — Is It Actually Useful?

What happens when you give AI a real bookkeeping problem: uncategorized transactions**? Everyone is talking about AI replacing bookkeepers. But I wanted to test something much more practical: **Can AI actually help clean up uncategorized transactions during month-end close? ** For this test, I used a fictional practice company and gave AI a set of uncategorized bookkeeping transactions. I wanted AI to do more than simply suggest an expense account. I tested whether it could help identify: • What the transaction might actually be • Possible GL/account classifications • Vendor and transaction context • Transactions that need more documentation • Possible duplicate transactions • Potential fixed-asset purchases • Contractor transactions that may require a W-9 / 1099 review • Payout transactions where gross vs. net revenue needs verification • Situations where AI should NOT guess And the most interesting result? **AI was useful—but not in the way I expected. ** Some transactions were reasonably clear. Others required documentation before I would feel comfortable posting them. That’s the part I think business owners and bookkeepers need to understand: **AI can speed up the investigation. It does not replace accounting judgment or supporting documentation. ** This video walks through the test, what AI got right, where it struggled, and how I would actually use AI in a month-end close process. The company and transactions used in this test are fictional practice data and are not based on confidential client or employer information. If you're a U.S. business owner, bookkeeper, or CPA looking at how AI can fit into your bookkeeping workflow, this is the kind of practical experiment I'll continue testing. #Bookkeeping #AIbookkeeping #SmallBusinessAccounting