When CPQ decides to just not work as expected, rerunning the install scripts from the Managed Package page should be a first stop.
The key indicators of when to run the rules is when
- CPQ throws an error with the phrase “Field Metadata” in it
- A price rule condition stops working or is not considered
- When you as an admin insert a bunch of fields or new picklist values
- CPQ just chooses to skip rules when they are active
Yes CPQ can sometimes act strange but there are some fixes out there.