Adding Variants to Older Listings

I want to add variants to existing listings (they’ve been up on the website for a year). Up until a certain product number that worked just fine. Now it won’t do it anymore. I can still create new listings with variants - no problem here. But that would take forever.
I already condensed ~50 listings down to ~20 this way and, of course, I also updated all the product numbers (e.g. former SMJ10056 is now SMJ10024). Where is the problem and how do I fix it? I’d like to update at least one category before my next convention…