Did Jesus tell his disciples beforehand that he would die and rise again?

Both are true, and the Gospels themselves explain how. Jesus did tell his disciples, more than once and plainly, but they did not understand it or take it in. Mark says after the second prediction that “they understood not that saying, and were afraid to ask him” (Mark 9:32); Luke says after the third that “they understood none of these things: and this saying was hid from them” (Luke 18:34). Coming down from the mountain of the transfiguration they were “questioning one with another what the rising from the dead should mean” (Mark 9:10), and when Jesus first spoke of his death Peter rebuked him (Mark 8:32). They expected a Messiah who would reign, not one who would be killed, and a promise of rising again made no sense to them until it happened.

John 20:9 says the same thing from the other side. What the disciples did not yet know was “the scripture”: they had not yet grasped from the Old Testament that the Christ must rise. John does not deny that Jesus had told them. He reports such sayings himself (John 2:19; 16:16), notes the disciples’ puzzlement (“we cannot tell what he saith”, 16:18), and says that after the resurrection “his disciples remembered that he had said this unto them; and they believed the scripture, and the word which Jesus had said” (John 2:22). Luke tells it in the same way. At the tomb the angels said “remember how he spake unto you”, and “they remembered his words” (Luke 24:6, 8). Told beforehand and understood afterwards: that is the picture all four Gospels give.