This has been an issue for ages. Sometimes when you die in a Greater Rift and you select to respawn at the last checkpoint, you’ll respawn at the entrance of the rift rather than at the entrance on the floor you died on.
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And its f…ing pain, why it havent been fixed yet is beyond me !
I’ve seen this reported many times over the years. So, it’s rather ironic that I still haven’t checked this out in all the GRifts I’ve run.
But, I don’t think a Checkpoint is created each time you enter a subsequent GRift Level. And even though I don’t remember ever getting a Reached Checkpoint Toast Window on first entering a GRift, I think the game automatically considers the entrance of Level 1 as a Checkpoint.
The best thing to do would be to create a thread on the General Discussion Forum suggesting a Quality-of-Life change to have a Checkpoint created upon entering each Level of a GRift. I’m sure you would get a lot of support from other players.
Currently though, I doubt if Blizzard considers this an issue, which is why it’s never been “fixed”.