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Another thing you could try to trigger it is start a map, replace the default members on the field with some reserve guys then save. Start the battle then surrender and try again. I believe this is when I saw both the portrait swapping and mixing/losing of items. Even closing the game and reloading the save file did not work, it somehow saved with the items missing.

Here you can see a screenshot of my Photokineticist wielding a steel sword like a boss -  :o

If you want my save file let me know.

I once noticed that the portrait order had changed in the game after reloading as well. I think some equipment had been copied at that time as well.

This is exactly what I am noticed as well. It also seems to have something to do with restarting the battle. I noticed it once before but had just started the game and thought maybe the weapons broke and I didn't notice. This time however, all of my Bandits throwing axes were gone (after restarting the battle in the tavern with the band of thieves) so I went to investigate and I noticed my Golem had changed spots and on of my heroes had the propeller item that was equipped on him (she had it equipped magically).

Thinking back, I had one battle that started and somehow my Mantis Rider had a crossbow equipped for the whole match too. I assume this was due to some item swapping seeing as he couldn't have equipped it otherwise and could not again after.