Why isn't this script moving my ImageLabel correctly?

Why isn't this script moving my ImageLabel correctly?

What I want it to do is to select a random position(based on the values the ImageLabel has as descendants),until a certain value is equal to another value, but it won't, it will only move 1 time.. why?

Any help is greatly appreciated!

The ImageLabel - movement starts at line 57

My code is as follows:

local RS = game.ReplicatedStorage
local ItemFolder = RS:WaitForChild("Items")
local Items = ItemFolder:GetChildren()
local Player = game.Players.LocalPlayer
local PlrGui = Player:WaitForChild("PlayerGui")
local BoxGui = PlrGui:WaitForChild("BoxGui")
local Arrow = BoxGui.Frame.Arrow
local ArrowPositions = Arrow:GetChildren()
local CurrentPos = Arrow.pos1.Value

local Label1 = BoxGui.Frame:FindFirstChild("1")
local Label2 = BoxGui.Frame:FindFirstChild("2")
local Label3 = BoxGui.Frame:FindFirstChild("3")
local Label4 = BoxGui.Frame:FindFirstChild("4")
local Label5 = BoxGui.Frame:FindFirstChild("5")


script.Parent.MouseButton1Click:connect(function()

    ---///SELECT RANDOM "ITEMS"
    local TimesToMove = math.random(7,14)
    print(TimesToMove)
    local Moved = 0

    local One = Items[math.random(1,#Items)]
    Label1.Text = One.Value

    local Two = Items[math.random(1,#Items)]
    if Two == One then 
        repeat Two = Items[math.random(1,#Items)] 
        until Two ~= One
    end
    Label2.Text = Two.Value

    local Three = Items[math.random(1,#Items)]
    if Three == One or Three == Two then 
        repeat Three = Items[math.random(1,#Items)] 
        until Three ~= One and Three ~= Two 
    end
    Label3.Text = Three.Value

    local Four = Items[math.random(1,#Items)]
    if Four == One or Four == Two or Four == Three then 
        repeat Four = Items[math.random(1,#Items)] 
        until Four ~= One and Four ~= Two and Four ~= Three
    end
    Label4.Text = Four.Value

    local Five = Items[math.random(1,#Items)]
    if Five == One or Five == Two or Five == Three or Five == Four then 
        repeat Five = Items[math.random(1,#Items)] 
        until Five ~= One and Five ~= Two and Five ~= Three and Five ~= Four  
    end 
    Label5.Text = Five.Value


    ---///START ARROW MOVEMENT
    repeat 
        local Position = ArrowPositions[math.random(1,#ArrowPositions)]
        if Position.Value == CurrentPos then
            repeat
                local Position = ArrowPositions[math.random(1,#ArrowPositions)]
            until Position.Value ~= CurrentPos
        end
        Arrow.Position = UDim2.new(Position.Value)
        CurrentPos = Position.Value
        Moved = Moved + 1
    until Moved == TimesToMove


end)