Hipot testers usually connect one side of the supply to safety ground (Earth ground). The other side of the supply is connected to the conductor being tested. With the supply connected like this there are two places a given conductor can be connected: high voltage or ground.

When you have more than two contacts to be hipot tested you connect one contact to high voltage and connect all other contacts to ground. Testing a contact in this fashion makes sure it is isolated from all other contacts.

If the insulation between the two is adequate, then the application of a large voltage difference between the two conductors separated by the insulator would result in the flow of a very small current. Although this small current is acceptable, no breakdown of either the air insulation or the solid insulation should take place. Therefore, the current of interest is the current that is the result of a partial discharge or breakdown, rather than the current due to capacitive coupling.