Hi there, @WABBQ - when you are processing a Paid Out, the cash taken out during this action should automatically cause your cash drawer to reflect a negative expected amount, if there is indeed a negative expected amount. 

For example: 

If you start your cash drawer with $100, then process a Paid Out in the amount of $500, your cash drawer should reflect a negative expected amount of $400.

Please let us know if this doesn't quite get you where you need to be, or reach out directly if you'd like a Customer Success team member to take a closer look at your account.