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First of all, I bow to you AK|Phantom for  your work and amazing collection! Very awesome, sir!

I love this game, I love that it's moddable and customizable and I love that people are adding stuff to the game!

Now I humbly ask: Is there a way for the game to auto-assign bodies/portraits to slaves in your mansion? I installed the "Improved Random Portraits" mod (also big thanks to the author of that mod) but I already have a savegame with quite a few slaves in the mansion. They have no portrait right now (even Chloe lost hers) :(

Will I need to manually assign the portraits? Or is there a smart function for the game to auto-assign to slaves you already own?

You are looking in the wrong thread.  Neither the portrait packs nor the vanilla game have anything to support auto-assigning portraits to existing slaves.
However, the Improved Random Portraits mod has exactly that:
"Added a "Random Portrait" button to the slave customization panel. Clicking this let's you re-roll a portrait for a slave."
If the button isn't present, then you have probably applied the mod wrong, likely the "randomportraits" folder is misplaced.

Ahh. Yes I found it now. Thank you so very much! :D