Pearl's Pearl is an item exclusive to DST, introduced in Return of Them. It can be obtained from the Crabby Hermit by following her questline.
Its main purpose is to be socketed into the Crab King for the boss fight. Socketing the pearl buffs the Crab King significantly, but it makes the King drop the Inactive Celestial Tribute. When the Crab King is defeated, Pearl's Pearl turns into a Cracked Pearl.
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*Examination Quotes*
Wilson:
I’ll take good care of it.
Willow:
Don’t worry grams, it’s safe with me!
Wolfgang:
Will take good care of shiny stone!
Wendy:
I will be its caretaker.
WX-78:
I WILL TAKE THIS AS PAYMENT
Wickerbottom:
Oh dear, I do hope I can find him.
Woodie:
C’mon Lucy, let’s find that crab!
Maxwell:
It’s... strange to be so trusted.
Wigfrid:
I shall prötect it with my life!
Webber:
We’ll take really good care of it!
Winona:
I know a bit about not givin’ up on someone.
Warly:
Madame Pearl entrusted this to me.
Wortox:
A treasured treasure.
Wormwood:
Shiny!
Wurt:
Oooooh, so shiny!
Walter:
I gave my Pinetree Pioneer oath to protect it with my life!
Wanda:
I’ll do my best.

The Cracked Pearl is the second form of Pearl’s Pearl, and can only be retrieved from the Crab King after it is defeated. It can be given back to the Crabby Hermit for extra dialogue.
WX-78’s quote for the Cracked Pearl may be a reference to the Call of Duty death message when the player dies from falling.
*Examination Quotes*
Wilson:
I... didn’t take good care of it.
Willow:
Oops...
Wolfgang:
Wolfgang did not take good care of shiny stone.
Wendy:
I seem to leave only misery in my wake...
WX-78:
MISTAKES WERE MADE
Wickerbottom:
I should tell her.
Woodie:
I was only trying to help...
Maxwell:
Ah. I thought I’d run out of people to disappoint.
Wigfrid:
The battle is wön, but at what cöst?
Webber:
We hope Ms. Pearl isn’t too mad at us...
Winona:
I’m so sorry, Pearl.
Warly:
Oh... oh dear...
Wortox:
A shattered hope.
Wormwood:
Broken...
Wurt:
D-didn’t do it!
Walter:
Oh no, oh no no no no...
Wanda:
I was holding out hope things would go differently this time.
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