For the cushion, I don't show it on paper. For example, I log in to my online banking and see that I have 300$ available, but on paper I show 200$ since my cushion is 100$. All that I would move to the next month is the 200$. As for expenses, I write them down when I pay them. For example, if I paid a bill on 1/30 but it didn't clear until 2/2, it went on January's expenses and I give it a check mark to show it cleared. When I rolled over my January bank balance I deducted everything that was still pending (waiting to clear) in my checking from that amount as if they had already cleared, and that balance is what I show as my rollover and starting balance for February :)