Dang it, Milo! Use your surprise attack on the Dark Lord to deliver a killing strike, not a standard attack!

If it’s any consolation, I’m pretty sure it was an Attack of Opportunity, so he could only use a physical attack and not a spell. Surely something Riddle was doing, between the grappling and the tentacles and the sword and the not expecting Milo and performing the ritual would provoke an AoO. On the other hand, definitely stating so would require me to actually understand 3.5’s grapple rules, and in the time it would take me to do that I could do something useful, like make cookies or get a second degree or solve poverty.