Using Classic Outlook on Windows for personal email, calendar, and contact management
I'm also having the same problem. I missed a meeting this morning because of the lack of a reminder.
I've been through all the troubleshooting suggestions (reminders turned on, run outlook /cleanreminders, check storage directory is in the right location, etc). It might sometimes generate a reminder, but then fails with other meetings.
This is obviously a problem affecting a number of people. Please prioritise fixing it. This is what the business world uses Outlook for.