If I made a purchase in April and I'm getting reimbursed for it in May, what's the best way to reflect this in YNAB? I have the cash to cover the purchase so I'm basically borrowing the cash from myself while I wait for the reimbursement to come in

This thread may be helpful

you could categorize the payment as cash spending / reimbursements ( if you have category for that already, and if not make one). When the reimbursement comes in add it to your ready to assign and then just refill the budget. (Don't worry about dates because in the end they cancel each other out.)

So I did that for the payment I made in April, but when the month changed over to May, the budget reset to 0(it was minus $$) and I think the debt went to my credit card (which I used to pay for the charge). If I assign the reimbursement back into that category when it comes in, I think it would just show as a positive balance available to spend... So maybe I should just assign it to the credit card directly? I was hoping that the negative balance in my reimbursement category would roll over to May but it didn't

So then go to april put in the reimbursement transaction on any date after the initial charge ( make up a date ) but before may 1st. Then in the notes write the actual date the transaction took place.

Yeah I guess I can do that, I was just hoping there would be a more intuitive way without playing around with dates

I would also check out the thread here: https://frumfinance.slack.com/archives/C04FDNE1056/p1715119461928869?thread_ts=1715118129.923359&channel=C04FDNE1056&message_ts=1715119461.928869 Rather than play with the dates, try to figure out how to record things in most accordance with reality… the money came from somewhere…