Action Icon Disappearing

[TJCobb1]

Hi. I was hoping someone can help with this mystery. I have created a simple Action that just changes a column to "Yes" with pressed. It works fine when I first set it up, but then when I try to use it on a different record, or just click away and come back to the same record, the Action icon disappears.

Just to make sure there wasn't something with that column, I also tried to add an Action to other columns and I'm getting the same disappearing icon. 

Screenshots attached. Thank you in advance for your time and patience.