I've been fighting this as well.
Here's my situation, the easiest possible match:
- Two bank checking accounts at the same bank
- Transfer from one to the other
- Each transaction is on the exact same date for the exact same amount
- Each transaction has the EXACT same Memo line
- WEB TRANSFER (3287078) FROM x1129 TO x1520
- The number in parenthesis is a unique number for every transaction and is identical in both transactions in QBO
- Sometimes, it finds the match; sometimes, it doesn't. There is literally no difference between the two transactions that it handles differently.
I've attached an image showing 1 transaction that's paired and the rest that have a rule applied (yes, it does the same when the rule isn't active).
This is probably the most ridiculous, frustrating and undata related issue I face and we do big data.
Side note: Everyone reading this, make sure you actually do the survey it pops up and asks you to do
