Custom Fields Dashboard Issue

Good Morning, 

I'm hoping the community can help me brainstorm what might be going wrong with a few modules I"ve created in a dashboard. So I've recently created a dashboard in order to keep track of every step of my print buying process for the marketing team instead of using a spreadsheet and it's working beautifully, the problem is this---

If a module is for let's say letting me know the piece is currently in production. But the item is also an ad-hoc request, and had multiple proofs. If all three of those are checked in my custom field, it doesn't populate in my module that shows me all items in production. I think it's because all three custom fields are checked, however I need it to work so...here is a picture of the custom field in the dashboard...how can I have the module pull in all task that have the production custom field, regardless if it has others checked in the same custom field or not. 

Once I can get that fixed, I can fix a few other modules as well where the same issue is occurring and should be smooth sailing from there. 

Appreciate the communities help, thank you.