He was never going to get plugged back into the matrix without the machines replacing all the nerve wires and plugs in his body, and moreover, to get placed in a pod without endangering the Nebuchadnezzar (remember Neo was picked up covertly from the icky pool after being released). Sure, in revolutions Neo and Trinity sailed across the farms without interception but that was at high speed.

Cypher was essentially groomed by the agents, and was guaranteed the high life of the top 1% of the world. Nobody else could guarantee that. There was no incentive to be open with his crew (and he would've been banished from access to the matrix, sent to work in drugery in Zion).