[Mark McLeod]

When you reseat the connector (while the robot is Enabled) try tilting it towards the back of the Victor and inserting it, then if that fails try tilting it more towards the front and inserting it. Sort of probe with it through all angles. The internal connector might not be directly under the opening and the pins are probably sliding down the outside (of the inside).

As a test you could remove the cover from one Victor and that way be sure to make the connection, since the socket will be visible. Once you get one to work it'll give you confidence that the covered ones will work.
Or having a solid connection will reveal other issues.