Answer
First confirm a PDF is genuinely being generated at all for that print job — check the Print Manager screen for that specific job and see whether a working RMB 'Show Document(s)' option is available, confirming real PDF output actually exists; if no PDF was actually produced, the event correctly has nothing to fire on. Next, independently verify that BOTH the Event itself AND its associated Event Action are genuinely enabled — it's possible for one to be enabled while the other silently isn't, which blocks the whole chain with no error shown. Finally, for isolating the specific root cause, temporarily remove the event's report-ID matching condition entirely and retest — if the event now fires with no condition at all, the condition itself, rather than the PDF generation or the enabled/disabled state, is where the actual problem lies, even if the condition's syntax looks correct at first glance.