I'm about at my wit's end with Quicken Classic for Windows, due to what it is doing with various transactions. It appears to be making cash withdrawals from a checking account match up with deposit transactions in a savings account, creating transfer transactions out of whole cloth. This means if I change the transaction category to a cash withdrawal in the checking account, which it actually is, this overwrites the account number in the category field (because Quicken assumed this was a transfer between accounts), and Quicken deletes the transaction in the savings account (which was never a transfer from checking to begin with), thinking I've removed a transfer transaction. BAM, both accounts are now out of balance with the online balances.
I really cannot abide the method that Quicken uses to record transfers between accounts, versus expense/income categories. Since it's matching transactions erroneously and marking them as transfers, any corrections make both accounts out of balance.
Why does Quicken have to use the category field for flagging transactions as transfers? A transfer is a transfer. Just because $1,000 was taken out of a checking account for cash, and a different $1,000 was deposited into a savings account from another source, why must Quicken force that to be a transfer transaction between the checking and savings accounts? Doing that makes any changes to the category field (for either account's transactions) EXTREMELY PROBLEMATIC.
Transfer transactions in Quicken have become so awful, I'm about to stop using this product out of frustration.