Every time you run a case in the die, it must be re-lubed. Regardless of the lube used.
When it is very difficult to get a case into the die--STOP and regroup. Don't force it any further. I'm sure there's a youtube video on making your own stuck case remover if you don't own one. You may damage your decapping assembly when drilling/tapping the case if you cannot remove it through the top of the die. You will remember the hard lessons.
I have gone easy on the 1 shot in my previous posts because it DOES work when you follow the instructions to the letter, but I really do not like it much. As I said before, the only stuck cases I ever had in 30 yr reloading career were when I was using 1 shot.
ETA: IF you cannot remove the decapping assy, then back it off as far as possible before drilling the case. I found that unscrewing the die and screwing it in the press upside down is the easiest way to perform the case removal operation.
I don't remember the brand of your dies, but I know that RCBS and Dillon will send you a new decapping assembly free of charge if you tell them what happened. Yeah, the rest of the world could learn a lot about customer service from the reloading industry.