It works, with two conditions attached. Write access has to be switched on for that company from the Caribooks portal, because every connection starts read-only. And you have to read the first batch line by line, because what the assistant is doing is matching patterns in your own history, not applying your accountant's judgment.
First, agree on what "uncategorized" means
Two different piles get called by that name, and only one of them is reachable from a conversation.
- Bank feed items still sitting in For Review. These are not in your books yet. Accepting or excluding them happens in QuickBooks, on the banking screen.
- Transactions already posted to a catch-all account. Uncategorized Expense, Ask My Accountant, or whatever your file uses. These are in the ledger, and these are the ones to work on here.
Start by sizing the problem:
"How much is sitting in Uncategorized Expense and Ask My Accountant over the last three months? List the transactions with date, vendor, amount and account."
Match your own history, not a generic chart of accounts
This is the prompt that matters, and the phrasing carries real weight:
"For each of those, find how similar purchases from the same vendor were categorized over the past year and propose the same account. Where there is no history for that vendor, say so, propose something, and flag it."
The difference between "this vendor has appeared 14 times and always goes to Software subscriptions" and "I have never seen this vendor and I am guessing from the name" is the entire exercise. Ask for that distinction explicitly or you get one confident list with no way to tell the two apart.
Add your own conventions, because books have local rules that no amount of pattern matching will infer:
"Anything from that supplier goes to Cost of sales rather than Office supplies when the amount is over 500 $."
Review the batch before anything is written
Ask for the proposal as a table, in the conversation, before any change reaches QuickBooks:
"Show the proposed categorization as a table: date, vendor, amount, proposed account, and how much history it is based on. Do not change anything yet."
Then work down the flagged rows first. The ones with clean history you can spot-check. The ones without history you check every time, in the first month and in every month after. When you are satisfied:
"Apply the ones from vendors with consistent history. Leave the flagged ones for me."
Doing it in one reviewed batch rather than transaction by transaction is the actual time saving. Twenty small decisions read as a table take a few minutes. The same twenty in the QuickBooks interface take an afternoon.
What to check every time
- Sales tax codes. Getting the expense account right and the tax code wrong is the expensive kind of correct-looking. Ask which code was applied and whether it matches how that vendor was handled before.
- Anything that might be capital rather than an expense. That threshold is a policy in your file, not a pattern in the data.
- Personal or mixed-use spending. No history teaches this. You know which line it is.
- The entire first batch. Then decide how much of the second one you read.
Everything written lands in QuickBooks with an audit trail and stays editable there. That is your undo, and it is worth confirming you can find it before you run a big batch.
Where this is the wrong tool
Your categorization is stable. If the same 30 vendors hit the same 12 accounts every month, bank rules in QuickBooks do this for free, deterministically, and without you in the room. Write the rules first. Use the assistant on the leftovers, which is where rules always fail anyway.
You have a bookkeeper. They are faster at this than you are at prompting, and they carry responsibility for the answer. A better use of the connector is giving them the reports and the review pass, not replacing the categorization.
You want receipt capture. Different problem, different tool.
You are on QuickBooks Desktop. Online only, structurally.
And if you have not moved past read-only yet, this is not the reason to. Read-only is the right setting for the first week: it lets you check how well the assistant reads your books before it can touch them. The security page covers how the switch works, and the comparison covers which connectors can write at all.