I noticed two occasions like these:
- Upon lockpicking a chest with the Legendary Tinkering perk active: the gold gets automatically deposited directly to the player even with the mode active.
- Upon starting a game with certain classes that have gold from the start(Merchant, Joker, etc.)
Suggestion for workarounds:
- Make the starting area with the gate immune to breaking voluntary challenges, so the player can drop the gold immediately before descending to the dungeon and remain "penniless".
- Make the gold drop on the floor near the lockpicked chest as an ordinary drop while the mode is active.