I had one of my teen sims age up a few days before her twin siblings. She didn't graduate, but when the twins went to graduate, I found I could click on the town hall and have her graduate as well. I haven't tried it again, but if you aren't getting the option to graduate, maybe you can try to initiate the option yourself by clicking on the town hall once the sim has aged up to young adult?
I had that same thing happen.
I was a little upset I wouldn't get one of the graduation awards for my giant legacy wall of awards. But when his younger twin siblings aged up to young adult, I was able to get them to graduate together.
I had tried clicking the town hall before but I didn't see that option at all, until I got the message about graduation day.
So, could that be the reason, OP? Do they have siblings close to aging up or are they the only child?
Or maybe they were sent to a private school? I don't know if they get the graduation ceremony if they age up from teen away from home. It makes some sense that they wouldn't, (why get a diploma from the public school when you didn't go there?) but that's just a guess.
Failing that it sounds like a game issue, events not popping like they should. /: