Hello,

so i do currently have an If condition in the workflow that checks if that box is selected. See below, there's a green star by it. However, it's looking at the value of that check box when the demand was originally set to Pending Approval. 
So the flow is - demand is submitted. Moves through various states. Then when it's set to pending approval, task goes to and says check this checkbox if necessary. 

based on that, if it's checked, then an approval needs generated. 

So, basically the workflow as i currently have it setup is looking at the original value of that checkbox not the updated value. thanks again for the help!!