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Did Jesus know He was going to rise again from the dead?

Yes. Jesus knew all along why He came to the earth – to die for our sins.

From that time on Jesus began to explain to his disciples that he must go to Jerusalem and suffer many things at the hands of the elders, chief priests and teachers of the law, and that he must be killed and on the third day be raised to life. Matthew 16:21

“But I tell you, Elijah has already come, and they did not recognize him, but have done to him everything they wished. In the same way the Son of Man is going to suffer at their hands.” Matthew 17:12

When they came together in Galilee, he said to them, “The Son of Man is going to be betrayed into the hands of men. They will kill him, and on the third day he will be raised to life.” And the disciples were filled with grief. Matthew 17:22-23

He knew the exact date.

When Jesus had finished saying all these things, he said to his disciples, “As you know, the Passover is two days away—and the Son of Man will be handed over to be crucified.” Matthew 26:1-2

He tried to pass on this confidence of his return to his disciples, but it was too much for them to handle and took them a long time to completely understand.