Phone support told me that because I have multiple sales receipts with different customers, that QBO can't automatically match the deposit. 

I informed the rep that I've been matching transactions for over two years, and suddenly within the last week it stopped working. She just regurgitated the response that QBO can't match automatically because the transactions are from different customers. I again said it's been working for 2 years, there was a recent update on QBO and now it suddenly doesn't work. The option to match multiple transactions automatically isn't even on the match screen anymore.  I asked if it was a bug in the new version, or if it was intentional. She said something about it not matching because multiple transactions, she checked her internal resources...

I asked to escalate. There is a clearly a bug in the new version or the feature was removed.