Cypher became a Judas because he grew tired of struggle and just wanted to live in blissful ignorance again. In a way, he had every reason to be tired. The Machines had reset the Matrix and made humans relive the same narrative countless times. The only reason that it stopped is because The Machines took mercy on Neo or somehow were finally ready to pave a way forward where humans weren't irrelevant. Was it Neo's persistence that impressed the Machines or did the Machines have a plan for Neo all along and just needed to give him time to grow/ learn by repeating numerous iterations of a scenario just like a computer would?

In any case, the rabbit hole keeps getting deeper.

Oh my God I feel horrible after reading this I thought we can trust to Gunderson not so sure anymore I didn't know about his marriage