Currently, RoosterMoney does not allow children to go into overdraft or negative balance, however, this is something we're looking into.
In the interim, a workaround some parents have used to manage this is by creating a goal called "loan" or similar. If you know what you've advanced your child, you can create a Goal with this amount. This goal can then become their first priority to pay off. You can also edit a goal to add extra money if another 'loan' is made, which you can find the instructions for in the related article at the bottom of the page.