When using conditional word formulas, statements are not populating as expected, even when conditions are properly met.
Add "Keep Word Formulas" to the Document Package layout
Go to Salesforce Setup.
Search for Create > Objects.
Scroll down and click on Document Packages.
Scroll down to Page Layouts.
Choose the appropriate layout (DDP/Document Package/Custom DDP/etc).
Under Quick Find, search for "Keep Word Formulas", and then drag onto the Document Package layout.
Another indication that an IF Statement is populating incorrectly could be that either the True or False statements may contain quotation marks within the middle of a True/False Statement. For example: IF "<<This_Tag>>" = "True Statement" "False Statement with "quotation marks inside" of this Statement"
As a workaround, remove the quotation marks and add two single quotation marks before and after the word/phrase/sentence containing quotation marks within said statement