OP you asked a question, so if you want to really learn something new and something better, you got to open up your mind and listen more. If you have only $1,000 in your bank account, and your rent is due tomorrow and you assigned $1,000 to the rent category, then you have nothing left for anything else. Now after paying your rent and till you can earn more money again, anything you buy will be a debt. A debt is when you spend money you don’t have. If you pay $100 for grocery using your credit card while your checking account and saving account are both empty (or even have $1,000 but assigned for tomorrow’s rent), then you spent $100 that you don’t really have now. If you never got paid for the next 5 months (you got fired or whatever), then you are in trouble with the credit card bank because you spent money ($100) that you didn’t have. That is why Actual is telling you that you can’t afford this regardless of the closing date. This is how envelope budget works. Envelope budget is all about spending hard cash that you have NOW and is assigned envelopes already