See original idea discussion here: https://community.quicken.com/discussion/7884502/broken-feature-from-qm2007-linked-transfers-with-splits-are-separated-in-destination-account
Copy/pasted with light editing:
Why was this discussion closed? https://community.quicken.com/discussion/7878420/transfers-from-one-account-to-another-with-split-transactions
I have the same issue and it was not resolved in that discussion. It's about functionality from Quicken Mac 2007 that no longer works in Quicken Mac 2020.
See here for the definition of a linked transfer: https://www.quicken.com/support/transfers-quicken-mac
Issue: a linked transfer with multiple split lines going to the same account will show up as separate individual transactions in the destination account (it should be a single transaction in both accounts). Therefore, the destination account will not reconcile, because the bank downloads show one transfer for the sum of the multiple individual transactions QM2020 creates. In QM2007 the destination account would correctly have a single transaction that matched the bank-downloaded transaction. You could not access the split details in the destination account register, but that was better than QM2020 creating fake transactions that don't match the bank statements.
Use case: I used to let my mortgage lender escrow my property taxes and insurance. Now I self-escrow them. Every month I transfer $600 from my primary checking to a special savings account dedicated to escrow. $500 is for my property tax and $100 is for homeowners insurance. I want to track each escrow category separately (using the memo or tag field), so I use two split lines in the transfer. This QM2020 behavior means one of the two accounts won't reconcile properly; i.e. if I record the $600 split transaction in the savings account, then the checking account will have two separate transactions (one for $500 and another for $100) that do not match my bank's downloaded transactions. Swapping which account it's recorded in just moves the problem to the other account register.
Right now my workaround is to manually clear/reconcile the individual sub-transactions and manually delete the corresponding downloaded transaction from my bank - I don't like doing that because of the risk of mistakes. The only other workaround I can think of is to do two separate bank transfers every month so they're actually two separate transactions in both Quicken and my bank. But I'd rather not incur extra effort/transactions just to avoid this Quicken behavior. Are there other workarounds I'm not thinking of? How do we get this behavior changed? Is there a feature request I can +1?