jumping in to the well in the yawning portal now results in death, respawning back to the inn. I am not sure whether the achievement would still unlock, however with the new patch on preview, it is no longer a means of transport to undermountain
The achievement still unlocks if you die. It is still possible to survive and go through but it is either random or else there is something I couldn't find consistently.
"We have always been at war with Dread Vault" ~ Little Brother
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