To address your question, Jon, you need cash to be available in your account on the day the payment is scheduled to be processed. Otherwise, the withdrawal will be processed and could put your account into an overdraft position, with interest payable on the negative cash balance. If you have your investments at a brokerage, they may also reserve the right to sell securities if you are in a debit position. If you own mutual funds in your RRIF, your brokerage may allow for systematic withdrawals on a scheduled basis to coincide with your payment schedule. If you have an investment professional who manages your investments, they can ensure cash is available as needed. Some may create a “cash wedge” by having a certain percentage of your RRIFs (and other accounts) held in cash for withdrawal purposes.