Reliable way to trigger 'In Case of Death' quest correctly?

I've seen many posts saying how buggy this quest can be, where having Gale die is supposed to trigger a dialogue automatically and put his pouch in your inventory, when most of the time it does either one but not both, or neither.

I've only gotten the pouch to appear, but no dialogue. Has anyone found a way to reliably get both to trigger as they should? I'm near the end of Act 2 if that helps.