State Tree "Enter Conditions" not updating

Running into an issue where enter conditions for a state tree wont update to evaluate the current condition of the variable they look at.

For example, if they enter condition is for a boolean to be true, then setting that boolean as true by default will fire off the state tree. However, if it starts off false and then is set to true through gameplay, the State Tree does not recognize the condition is now true and doesn’t execute the State Tree Task. Is there something I may be doing wrong that I can fix?