Thanks for all your help. I do appreciate it. 
Does this happen for all files, or just this one PDF?
If you could upload the file and the exact smart rule you are using (showing exactly what is being searched for), we could try it ourselves and see if it is a local glitch or something bigger.
The PDF in question is private, but based on the feedback here, it should work. I’ll experiment with other PDFs and report back.
Thanks so much for your reply.
I had the same issue as you( you made a thread about it, too)
Apparently all I had to do is just move the smart rule to the top of the list.
For example having “perform the following actions: Synchronization” twice doesnt work unless you manually “Apply Rule” this is ridiculous because I can’t have no more than two synchronization actions.
I moved the rule to the top of the Smart Rules, but it made no difference.
Rule on import does not work. The PDF just sits in the inbox.
At this point, I smell bugs!
Yeah, see if the same thing happen with a PDF you could share. I’m trying it here with my own files, and On Import works find, so it’s gotta be some quirky little bug…
Agreed. Seems to work with other PDFs. Weird that Spotlight can find the text but DT can’t, but moving on…
Appreciate all the help and replies.