Using Classic Outlook on Windows for personal email, calendar, and contact management
Same problem here. Meeting reminders have been increasingly sporadic and unreliable on Outlook desktop (for Mac, v. 16.24).
I just went through and tried re-saving my recurring meetings, sometimes altering the amount of time for the reminder. I made sure to always edit the series, not just the occurrence. As I did this, I had several odd reminders pop up. Almost like I was getting them un-stuck. For example, I re-saved a series I've had running for a couple years, and it triggered a reminder for a meeting in August!
TBD if that helps going forward. (EDIT: It didn't. Next meeting on the calendar failed to trigger its reminder.) Best guess is that maybe at some point I altered an instance of the series and it messed up the notifications, and they can't get back on track as the series continues. Might try deleting series entirely and re-scheduling. But that's impractical for some meetings with others without bugging everyone to re-accept invites.
Significant bug, really needs addressing. Happy to provide more debugging information!