Receipt Matching: Pairing Paper With the Bank Charge

What Happens When You Upload

When a receipt image or PDF arrives, DynaTax AI extracts the details it needs to identify the purchase — the vendor, the total, and the date — along with a confidence score for how clearly it could read them.

Those three fields are the whole basis of the match. Everything below is about how they are compared against your bank feed.

How the Match Is Decided

DynaTax AI looks for candidate transactions within seven calendar days either side of the receipt date, then scores each one out of 100 across three factors.

Amount — worth up to 40 points

• Within 1% of the receipt total: full 40 points
• Within 5%: 35 points
• Within 10%: 25 points
• Within 25%: 15 points — this band exists for restaurants, where the receipt shows the meal and the card is charged with the tip added

Date — worth up to 30 points

• Same calendar day: full 30 points
• One day apart: 25 points — the ordinary overnight posting delay
• Two to seven days apart: 20 points. Still inside the window, but a multi-day gap is weak evidence on its own, so only a strong amount and vendor match can carry it

Vendor — worth up to 30 points

The vendor name on the receipt is normalized before it is compared, because the bank almost never shows the name the way the receipt does — store numbers, location codes and payment-processor prefixes get stripped out first.

When It Matches Without Asking

A receipt is linked to a transaction with no human in the loop only when both of these hold:

• The best candidate scores 90 or higher.
• It is the only candidate scoring 80 or higher.

The second condition is the one that matters. Two coffees at the same shop on the same day for the same amount are indistinguishable to any scoring system — so when the field is genuinely ambiguous, DynaTax AI declines to guess and hands it to you instead of picking one at random.

Unmatched Receipts

A receipt sits in Unmatched Receipts when no bank charge has turned up that explains it. The usual reasons, in rough order of frequency:

• The charge has not posted yet. Card charges often take a day or two to reach the bank feed. This resolves itself.
• You paid in cash. There is no bank charge to find, and there never will be. A cash expense is a perfectly normal outcome, not an error.
• It was paid from an account you have not connected. A personal card, a second business account.
• The amount does not agree. A partial refund, a split bill, or a charge that landed outside the 25% tip band.

DynaTax AI keeps looking for a bank charge for 14 days. It is deliberately much longer than the seven-day match window, so that a bank feed which simply synced late is not mistaken for a cash purchase. After that the expense settles as cash and stops waiting.

Transactions That Need a Receipt

The reverse queue, Need Receipts, works from the other direction: bank charges you have coded as business expenses that have no receipt attached.

The cutoff is $75. That is not an arbitrary round number — it is the amount at or above which the IRS expects documentary substantiation for a business expense. Below it, a bank record is generally enough on its own; at or above it, an undocumented expense is the kind of thing that does not survive scrutiny.

Getting Better Matches

• Capture the total, not just the itemized lines. The total is what the bank charged, and it carries the most weight in the score.
• Get the whole receipt in frame. A cropped date or a cut-off vendor name removes an entire scoring factor.
• Upload close to the purchase. Same-day uploads land in the strongest date band.
• For restaurants, photograph the copy you signed — the one with the tip written on it — so the total agrees with the card charge instead of relying on the tip band.
• Connect every account you spend from. A receipt from an unconnected card can never be matched.

Frequently Asked Questions