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Buy nowAfter posting, I see this thread is about QB Desktop. The following is applicable for QBO.
For what it's worth to anyone else who runs across this, here's the behavior I've seen in QBO while trying to troubleshoot this:
1. If the transaction is entered as a "Check" and has a numeric "Check No" value in that field, QBO will not auto-match it to bank transactions unless that number is in the Bank Detail text.
2. If the transaction is a "Check" and something else (like "ACH" or "Transfer"), QBO will auto-match to a bank transaction that matches the amounts and is close in dates.
See screenshots below.
My takeaway? If you're paying something by ACH or Bank Transfer or Zelle or anything other than a traditional paper check, indicate a textual payment type in the "Check No" field. It's more accurate, and makes life just a little simpler.
NO AUTO-MATCH
SUCCESSFUL AUTO-MATCH