You are missing the increment of the counter, the code never hits it, improved code below

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--Set Variables for randomizing Information, et al

DECLARE @localChestTier int, @ItemLimit int, @counter int,@ItemCounter int

SET @counter = 1 -- outter chest counter

SET @ItemCounter = 1 -- inner Items in each chest counter

WHILE @counter <= 1000 -- create 1000 chests full of items

BEGIN

SET @localChestTier = 1; -- (SELECT Chests.ChestTier FROM Chests WHERE Chests.ChestID = @counter) -- Pulling item quality base line... TODO: this seems very rigid, examine better methods of implementation

SET @ItemLimit = 10 --(ABS(CHECKSUM(NEWID())) % (@localChestTier * 2)) + 1 -- double base tier for item cap

BEGIN

WHILE @ItemCounter <= @ItemLimit

BEGIN

INSERT INTO ChestItems --Join Table

SELECT

--ChestItemsID Primary Key Auto incremented

@counter,--ChestID from Chests

(SELECT TOP 1 Items.ItemID FROM Items WHERE Items.ItemTier = @localChestTier)--ItemID from Items

SET @ItemCounter +=1 -- next item

END

SET @counter += 1 -- next chest

END

END