Skynet's plan was to make sure humans win the war.
Maybe it regretted the 'judgment day' and realized its wrongdoings, but things had already gotten out of its digital hand.
So it hatched this plan, where he would make sure a SAVIOUR OF HUMANITY would appear, and it would have the initials J.C., and then it would be inseminated by a future being instead of a regular dude.
In any case.. by sending a terminator to 1984, to 'supposedly kill Sarah', the humans had to send Kyle Reese back to 1984 to protect her, and more importantly inseminate her so that saviour could be born and bring end to the destructive conflict and bring peace to humans and machines alike, so humans can finally subdue machines back to slave status (maybe Skynet is masochístic?).
The only way Skynet could've won the war, was to not send a terminator back to 1984. This would mean humans would also not send anyone back to 1984. This would ensure there's no saviour, because the saviour's father never goes to 1984 to inseminate anyone. Game over for humans! All Skynet had to do was 'nothing' to win!
Therefore, it WANTED to lose, because it did something drastic to alter its own destiny. It was intelligent, it must've known all this, so its plan was basically 'human-assisted suicide'.
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