To clarify for myself and the OP.
This only applies to AC coupling on a AC signal with a DC offset. Or a DC signal on AC coupling.
Assuming no charge on the coupling cap, no harm can be done to the initial connection other than it taking a while for the coupling cap to charge up to the DC offset level.
Once the coupling cap is charged to whatever the DC offset voltage is, When moving to another point in the circuit it will have that charged cap voltage available to possibly discharge into the new measurement point.
Is this correct?