Ah, let me rephrase that...
Actually whats happening, is this field is being called in the product listings view. Then if I toggle the options and choose the second one and go through checkout, it is not being applied to the product (the serial number) // which means I dont see it in the order created email... However if I go through to the product page and apply the second option - it is applied to the product - and I see it in the order created email.
So for some reason the option although it displays in the product listing and it goes reflect in the text if I select it (reflect in the text of checkout) - the actual serial is not applied... Is there something I can add to the product listings view to ensure the serial is applied if a custom field option is selected?