How to fix Mouse Enter and Mouse Leave Not Working / Not Being Consistent Problem?

Hello there! I have a problem I just can't quite seem to fix and it makes no sense to me.

Full Code

df = script.Parent:WaitForChild("DefaultItem")
items = script.Parent:WaitForChild("Items")
trails = game.ReplicatedStorage:WaitForChild("Trails")

-- df means default

df.Visible = false

CurrentData = script.Parent:WaitForChild("CurrentData", 999)
EquippedItem = CurrentData:WaitForChild("EquippedItem", 999)
OwnedItems = CurrentData:WaitForChild("OwnedItems", 999)

function update()
	for i, v in pairs(trails:GetChildren()) do
		if not items:FindFirstChild(v.Name) then
			local trail = v:FindFirstChild("Trail")
			local trailtype = v:FindFirstChild("TrailType")
			local icon = v:FindFirstChild("Icon")
			local price = v:FindFirstChild("Price")
			
			if trail and trailtype and icon and price then
				local clone = df:Clone()
				
				local itemicon = clone:WaitForChild("Icon", 999)
				local text = clone:WaitForChild("Label", 999)
				
				itemicon.Image = "rbxassetid://"..icon.Value
				text.Text = tostring(v.Name).." - "..tostring(price.Value).."XP"
				clone.Visible = true
				clone.Name = tostring(v.Name)
				clone.Parent = items
				
				
				-- Setup Color
				local round = clone:WaitForChild("Roundify", 999)
				
				equippedcolor = Color3.fromRGB(55, 255, 95)
				ownedcolor = Color3.fromRGB(255, 136, 0)
				nilcolor = Color3.fromRGB(231, 231, 231)
				hovercolor = Color3.fromRGB(37, 173, 231)
				
				local defaultcolor = nilcolor
				
				
				
				-- StartColor
				
				if EquippedItem.Value == clone.Name then
					defaultcolor = equippedcolor
				elseif OwnedItems:FindFirstChild(clone.Name) then
					defaultcolor = ownedcolor
				else
					defaultcolor = nilcolor
				end
				
				-- Set Start Color
				round.ImageColor3 = defaultcolor
				
				-- Mouse Control
				clone.MouseEnter:Connect(function()
					round.ImageColor3 = hovercolor
				end)
				
				clone.MouseLeave:Connect(function()
					round.ImageColor3 = defaultcolor
				end)
				
				clone.MouseButton1Click:Connect(function()
					if OwnedItems:FindFirstChild(clone.Name) then
						if EquippedItem.Value == clone.Name then
							EquippedItem.Value = ""
						else
							EquippedItem.Value = clone.Name
						end
					else
						local own = Instance.new("BoolValue")
						own.Name = clone.Name
						own.Parent = OwnedItems
					end
				end)
				
				OwnedItems.ChildAdded:Connect(function(child)
					if child.Name == clone.Name then
						defaultcolor = ownedcolor
					end
				end)
				
				OwnedItems.ChildRemoved:Connect(function(child)
					if child.Name == clone.Name then
						defaultcolor = nilcolor
					end
				end)
				
				EquippedItem.Changed:Connect(function()
					if EquippedItem.Value == clone.Name then
						defaultcolor = equippedcolor
					elseif OwnedItems:FindFirstChild(clone.Name) then
						defaultcolor = ownedcolor
					else
						defaultcolor = nilcolor
					end
				end)
			end
		end
		
	end
	
	for i, v in pairs(items:GetChildren()) do
		if not trails:FindFirstChild(v.Name) and not v:IsA("UIGridLayout") then
			v:Destroy()
		end
	end
end

trails.ChildAdded:Connect(function()
	update()
end)

trails.ChildRemoved:Connect(function()
	update()
end)

while true do
	-- Update
	update()
	wait(3)
end

The problem is, it creates a list of all the in game trails you can buy with XP for my game. It does that okay but the problem is the Mouse Enter and Mouse Leave is inconsistent. Here's what happens. If the item was already there when I started the game, the item doesn't work. If I add the item in at runtime, the mouse enter / leave works. If I cut on of the items that was there when it started, the mouse enter / leave works. If it stays there and it was there when the game started, it doesn't work. My simple script makes the icon blue when hovered and then back to grey when not hovering. But it's so inconsistent. Why does this happen? I'm guessing it's because something isn't loaded up quite right yet. But what isn't? Have you guys got any ideas I would be extremely grateful to have a fix and an explanation for this.