Most recently happened with my 3DS. I have done two system transfers, one from the original model to the XL, then from the XL to the New 3DS XL.
First transfer went fine. Not sure what went wrong on the second one but I lost all save data for Steamworld Dig, A Link Between Worlds, and Majora's Mask 3D. Wouldn't have minded really but all three were games I had not completed. Still haven't to this day in fact.
As a slightly adjacent story to this topic, I have had a few bad experiences with games that do not auto-save. Way way back, with Pokémon Emerald on GBA, I played for about 2-3 hours at one point only to turn the game off without saving. I realized what I had done moments after shutting it off. More recently, when playing Majora's Mask 3D (this is after the debacle above) I completed the entire second when suddenly the screen went black and gave me the power down/sleep mode option. I think I must have accidentally rested my hand on the power button.
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