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(+2)

yeah I'm almost certain that is what you'd need to do or at least go back to a save just before you trigger the order's arrival and do all of his pup content, that's what I did and while I think you don't think you need to do all his pup scenes first I say do them all just in case

 

Oof. My save was pretty much caught up to the current update otherwise, and I have no clue how far back my last non-quicksave was. Whoops. I think I may put this one on the backburner for a little while if that's the case. Thanks for responding though!

I will say always remember to make multiple save files. Renpy has an endless amount and you can always make your own save folds and rename everything. Helps with this game and others to revisit scenes as well, or catch something you might have missed once you learn about it.