Connectors on wires entering a plastic box
I have used listed clamps on construction boxes but black button connector is a device like an “insider” plastic clamp it is only listed for 1 direction. Mechanical 2 screw clamps can be installed with the screws on the inside or outside. On plastic boxes if you have a bushing to protect the insulation the staple needs to be within 8” not all plastic boxes have clamps but if you drill a hole it will require protection for the wire at a minimum. I would say based on that it doesn’t matter but if the instructions for your clamp provide a direction the inspector can flag it.