If you use the checkpoints’ CFrame instead of position, you’ll get more consistent behavior as it includes the rotation of the part:
HumanoidRootPart.CFrame = checkpoint.CFrame + Vector3.new(0, 2, 0)
Additionally, you can multiply that CFrame with the CFrame.Angles I wrote in my previous post if the rotation is still off. But using the checkpoints’ CFrame you really just need to rotate the checkpoints the right way to fix your issue.