Indeed, that is a corrupt design for a bulkhead. Anyone selling that crap should be ashamed. The real flaw is that liquid can easily seep between the coupling and the SS washer, gain access to the threads and just spiral right inside that oring. In other words, that oring cannot stop liquid in the valleys of the nipple.
You never want to use a gasket on the outside of a cooler because if that's stopping liquid at that location, it means liquid is then able to fill the cavity between the two shells soaking the insulation. That's bad for heat retention but also disgusting.
Aside from buying a properly designed bulkhead like this one:
True Weldless Bulkhead - With Large BARB
View attachment 728497
You may try reconfiguring the one you have. Remove the external oring (for reasons above and the fact that it adds unnecessary flex). Then get some aquarium repair silicone and goop it up everywhere on the inside parts.