How do I set up a learning alert which uses course category?

We need to set up a learning alert that refers to course category as one of the expressions.

I've found an expression for this:

Resource: learnerLearningCatalogItems/courseDFF
Expression: ${courseCategory} = 'Regulatory'

However, we also need to use the expressions ${assignmentStatus} = 'ORA_ASSN_REC_ACTIVE' and ${assignmentDueDate} < sysdate

These come from the Resource: learnerLearningRecords

The alert won't run, is this because I've used expressions from two different Resources?

Can anyone help me with how to rectify this?