As catagory I am not sure what to place it as but… from my research, Chiltara spawns every single time for me. Though it only suppose to sometimes spawn. And I believe it spawning every time Is making the Gibbering Gemstone harder to get. I killed The boss 248 times now and have gotten nothing… is this a bug or am I just lucky-ish.
No, chiltara doesn’t spawn every time for me.
Are you mistaken it with another unique mob (I forgot it’s name)?
Zelusa the Grasping. They’re both lacuni huntresses so could be an easy mistake for OP to make.
If Chiltara really does spawn every time for you, OP, you’re very lucky. The Gibbering Gemstone has a really low drop-rate, so the fact that you haven’t got it yet isn’t a bug, just RNG.
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honestly I’m at a point where I want to continue playing, but this is a massive wall that I can’t get past. Seeing people struggle and give up after so many attempts encourages me to do the same. Its sick how many posts there are about this, but everyone is just like OH WELL ITS RNG. I wish there was a way for the game to understand how many times this creature has died for some players and just grant the gg. It’s not like we aren’t trying hard enough to get it. why does this have such a low drop rate? I’ve been at it for almost a week now, this is boring and dumb.
Only One week? Geez, what a quitter. 
Blizzard is all about THE GRIND! If they weren’t getting complaints that something is too hard to come by, they’d probably lower the drop rate even further. I am guessing their logic is that It’s like sex, if it was easy to get, you’d quit having it, right? Oh Wait!!! NO YOU WOULDN’T!
I’ve gotten the gemstone 5 or 6 times in seasons. In some it was literally weeks of attempts until it dropped. In at least one season, it dropped on regular player and then the very next day on my HC player. So, yes, it is just RNG and Blizz RNG hates players. Goo Luck and remember to check only the games where the Frost Cavern is a bounty. If you don’t see it as a bounty, restart the game.
i mean gaming to me is supposed to be fun and dynamic. I understand challenges and how great is it to accomplish something thats hard to get. When it gets to the point where you’re more frustrated than having fun and its no longer a real challenge and becomes tedius, its no longer a game, its work. I don’t want to continue anymore 
I have a job, I’m good on work. I’ll just play overwatch lol.
So go play overwatch?
No one needs a staff of herding. Whimsyshire doesn’t give you anything worthwhile that is gameplay related. It is a challenge for those looking for certain cosmetics only.
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I’ve only stumbled upon Whimsyshire once and i wanted to get the staff of herding, everything was a bit challenging to get until the gibbering gemstone, which took way too long. it turned from being excited to being so close to well i dont want to do this anymore. its lame! just raise the drop rate lol
No you didn’t. Whimsydale and Whimsyshire are different, even though they use the same type of map.
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\_(^ ^)_/ oopsies!
There is Whimsyshire and Whimsydale. Aesthetically both look the same. But how you can enter them and purpose of each are different.
If you don’t have Staff of Herding, it means you entered Whimsydale from killing a rainbow goblin. In Whimsydale, golds, mats, items rain from the sky, like heaven. This is the only place you can get Cosmic Wing from a very rare spawn (so rare spawn mob from a rare spawn portal).
Whimsyshire however, can only be entered using Staff of Herding. It can always be open one 100% of the time in each game. This is the only place you can farm rainbow portrait from a very rare spawn mob. This place doesn’t drop gold, mats, items from the sky.
So unless you’re specifically farming for rainbow portrait, there is little reason for you to farm Staff of Herding this early in your game. Make your char stronger, then farm for the portrait when you can steamroll mobs.
Both place can drop rainbow sword or hamburger xmog.
And no, Gibbering Gemstone being a rare drop isn’t a bug. It is said it drops better in T3, 4, 5 game, but rare drop is a rare drop, and it still drops in game.
As for OP, perhaps it has something to do with him only having D3 vanilla? If that isn’t an issue, again, rare drop simply is a rare drop. Staff of Herding only provides aesthetic stuff. Start farming it after your char becomes strong, not when your char is weak, taking long time to kill the mob.
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So I am for sure it was Chiltara spawning each and every time. Though I still feel like it spawning ever time is making it so the Gibbering gemstone doesn’t drop.
I started to farm chiltara (lvl 60 I do not have ros on that account). Like for OP, it is here at every run.
Edit: sometimes, I need to search it because it hides.
Edit 2: and it just dropped the GG.