This question/issue applies to all investment accounts managed through Quicken for Mac. It is particularly important for Fidelity brokerage accounts . The problem is that when entering a new transaction (e.g., by pushing the + button, the system no longer presents you with a Transaction Types or Category option that lets you choose, for example, a Payment/Deposit or other category. It only lets you specify a buy new stocks.
Fidelity brokerage accounts now can be treated like combined investment, checking and savings accounts. You can write checks from them, use bill pay, move money in and out and make investments. They make/market a special account for making this obvious but all (non retirement) brokerage can be used this way. I am using an account in this way and this bug really gets in the way of managing my transactions.