diff --git a/Classes/ItemsTab.lua b/Classes/ItemsTab.lua
index e5f853cc82..2875f4e99f 100644
--- a/Classes/ItemsTab.lua
+++ b/Classes/ItemsTab.lua
@@ -825,13 +825,15 @@ function ItemsTabClass:Draw(viewPort, inputEvents)
 	self.controls.scrollBarV.y = viewPort.y
 	do
 		local maxY = select(2, self.lastSlot:GetPos()) + 24
+		local maxX = self.anchorDisplayItem:GetPos() + 462
 		if self.displayItem then
 			local x, y = self.controls.displayItemTooltipAnchor:GetPos()
-			local ttW, ttH = self.displayItemTooltip:GetSize()
+			local ttW, ttH = self.displayItemTooltip:GetDynamicSize(viewPort)
 			maxY = m_max(maxY, y + ttH + 4)
+			maxX = m_max(maxX, x + ttW + 80)
 		end
 		local contentHeight = maxY - self.y
-		local contentWidth = self.anchorDisplayItem:GetPos() + 462 - self.x
+		local contentWidth = maxX - self.x
 		local v = contentHeight > viewPort.height
 		local h = contentWidth > viewPort.width - (v and 20 or 0)
 		if h then
diff --git a/Classes/Tooltip.lua b/Classes/Tooltip.lua
index be92d46ce2..34ac7ffec7 100644
--- a/Classes/Tooltip.lua
+++ b/Classes/Tooltip.lua
@@ -9,6 +9,12 @@ local m_max = math.max
 local m_floor = math.floor
 local s_gmatch = string.gmatch
 
+-- Constants
+
+local BORDER_WIDTH = 3
+local H_PAD	= 12
+local V_PAD = 10
+
 -- All possible values for notable recipes (oils)
 local recipeNames = {
 	"AmberOil",
@@ -35,17 +41,20 @@ end
 
 local TooltipClass = newClass("Tooltip", function(self)
 	self.lines = { }
+	self.blocks = { }
 	self:Clear()
 end)
 
 function TooltipClass:Clear()
 	wipeTable(self.lines)
+	wipeTable(self.blocks)
 	if self.updateParams then
 		wipeTable(self.updateParams)
 	end
 	self.recipe = nil
 	self.center = false
 	self.color = { 0.5, 0.3, 0 }
+	t_insert(self.blocks, { height = 0 })
 end
 
 function TooltipClass:CheckForUpdate(...)
@@ -71,12 +80,17 @@ end
 function TooltipClass:AddLine(size, text)
 	if text then
 		for line in s_gmatch(text .. "\n", "([^\n]*)\n") do	
+			if line:match("^.*(Equipping)") == "Equipping" or line:match("^.*(Removing)") == "Removing" then
+				t_insert(self.blocks, { height = size + 2})
+			else
+				self.blocks[#self.blocks].height = self.blocks[#self.blocks].height + size + 2
+			end
 			if self.maxWidth then
-				for _, line in ipairs(main:WrapString(line, size, self.maxWidth - 12)) do
-					t_insert(self.lines, { size = size, text = line })
+				for _, line in ipairs(main:WrapString(line, size, self.maxWidth - H_PAD)) do
+					t_insert(self.lines, { size = size, text = line, block = #self.blocks })
 				end
 			else
-				t_insert(self.lines, { size = size, text = line })
+				t_insert(self.lines, { size = size, text = line, block = #self.blocks })
 			end
 		end
 	end
@@ -117,7 +131,66 @@ function TooltipClass:GetSize()
 		ttW = m_max(ttW, imageX)
 	end
 
-	return ttW + 12, ttH + 10
+	return ttW + H_PAD, ttH + V_PAD
+end
+
+function TooltipClass:GetDynamicSize(viewPort)
+	local staticttW, staticttH = self:GetSize()
+	local columns, ttH = self:CalculateColumns(0, 0, staticttH, staticttW, viewPort)
+	local ttW = columns * staticttW
+
+	return ttW + H_PAD, ttH + V_PAD
+end
+
+function TooltipClass:CalculateColumns(ttY, ttX, ttH, ttW, viewPort)
+	local y = ttY + 2 * BORDER_WIDTH
+	local x = ttX
+	local columns = 1 -- reset to count columns by block heights
+	local currentBlock = 1
+	local maxColumnHeight = 0
+	local drawStack = {}
+
+	for i, data in ipairs(self.lines) do
+		if self.recipe and i == 1 then
+			local title = self.lines[1]
+			local imageX = DrawStringWidth(title.size, "VAR", title.text) + title.size
+			local recipeTextSize = (title.size * 3) / 4
+			for _, recipeName in ipairs(self.recipe) do
+				-- Trim "Oil" from the recipe name, which normally looks like "GoldenOil"
+				local recipeNameShort = recipeName
+				if #recipeNameShort > 3 and recipeNameShort:sub(-3) == "Oil" then
+					recipeNameShort = recipeNameShort:sub(1, #recipeNameShort - 3)
+				end
+				-- Draw the name of the recipe component (oil)
+				t_insert(drawStack, {ttX + imageX, y + (title.size - recipeTextSize)/2, "LEFT", recipeTextSize, "VAR", recipeNameShort})
+				imageX = imageX + DrawStringWidth(recipeTextSize, "VAR", recipeNameShort)
+				-- Draw the image of the recipe component (oil)
+				t_insert(drawStack, {recipeImages[recipeName], ttX + imageX, y, title.size, title.size})
+				imageX = imageX + title.size * 1.25
+			end
+		end
+		if data.text then
+			-- if data + borders is going to go outside of the viewPort
+			if currentBlock ~= data.block and self.blocks[data.block].height + y > ttY + math.min(ttH, viewPort.height) then
+				y = ttY + 2 * BORDER_WIDTH
+				x = ttX + ttW * columns
+				columns = columns + 1
+			end
+			currentBlock = data.block
+			if self.center then
+				t_insert(drawStack, {x + ttW/2, y, "CENTER_X", data.size, "VAR", data.text})
+			else
+				t_insert(drawStack, {x + 6, y, "LEFT", data.size, "VAR", data.text})
+			end
+			y = y + data.size + 2
+		elseif self.lines[i + 1] and self.lines[i - 1] and self.lines[i + 1].text then
+			t_insert(drawStack, {nil, x, y - 1 + data.size / 2, ttW - BORDER_WIDTH, 2})
+			y = y + data.size + 2
+		end
+		maxColumnHeight = m_max(y - ttY + 2 * BORDER_WIDTH, maxColumnHeight)
+	end
+
+	return columns, maxColumnHeight, drawStack
 end
 
 function TooltipClass:Draw(x, y, w, h, viewPort)
@@ -141,57 +214,41 @@ function TooltipClass:Draw(x, y, w, h, viewPort)
 	elseif self.center then
 		ttX = m_floor(x - ttW/2)
 	end
-	if type(self.color) == "string" then
-		SetDrawColor(self.color) 
-	else
-		SetDrawColor(unpack(self.color))
-	end
-	DrawImage(nil, ttX, ttY, ttW, 3)
-	DrawImage(nil, ttX, ttY, 3, ttH)
-	DrawImage(nil, ttX, ttY + ttH - 3, ttW, 3)
-	DrawImage(nil, ttX + ttW - 3, ttY, 3, ttH)
-	SetDrawColor(0, 0, 0, 0.75)
-	DrawImage(nil, ttX + 3, ttY + 3, ttW - 6, ttH - 6)
+	
 	SetDrawColor(1, 1, 1)
 
-	local y = ttY + 6
-	-- Draw the oil recipe for notables
-	if self.recipe and self.lines[1] then
-		local title = self.lines[1]
-		local imageX = DrawStringWidth(title.size, "VAR", title.text) + title.size
-		local recipeTextSize = (title.size * 3) / 4
-		for _, recipeName in ipairs(self.recipe) do
-			-- Trim "Oil" from the recipe name, which normally looks like "GoldenOil"
-			local recipeNameShort = recipeName
-			if #recipeNameShort > 3 and recipeNameShort:sub(-3) == "Oil" then
-				recipeNameShort = recipeNameShort:sub(1, #recipeNameShort - 3)
-			end
-			-- Draw the name of the recipe component (oil)
-			DrawString(ttX + imageX, y + (title.size - recipeTextSize)/2, "LEFT", recipeTextSize, "VAR", recipeNameShort)
-			imageX = imageX + DrawStringWidth(recipeTextSize, "VAR", recipeNameShort)
-			-- Draw the image of the recipe component (oil)
-			DrawImage(recipeImages[recipeName], ttX + imageX, y, title.size, title.size)
-			imageX = imageX + title.size * 1.25
-		end
-	end
+	local columns, maxColumnHeight, drawStack = self:CalculateColumns(ttY, ttX, ttH, ttW, viewPort)
 
-	for i, data in ipairs(self.lines) do
-		if data.text then
-			if self.center then
-				DrawString(ttX + ttW/2, y, "CENTER_X", data.size, "VAR", data.text)
-			else
-				DrawString(ttX + 6, y, "LEFT", data.size, "VAR", data.text)
-			end
-			y = y + data.size + 2
-		elseif self.lines[i + 1] and self.lines[i - 1] and self.lines[i + 1].text then
-			if type(self.color) == "string" then
-				SetDrawColor(self.color) 
+	-- background shading currently must be drawn before text lines.  API change will allow something like the commented lines below
+	SetDrawColor(0, 0, 0, .85)
+	--SetDrawLayer(nil, GetDrawLayer() - 5)
+	DrawImage(nil, ttX, ttY + BORDER_WIDTH, ttW * columns - BORDER_WIDTH, maxColumnHeight - 2 * BORDER_WIDTH)
+	--SetDrawLayer(nil, GetDrawLayer())
+	SetDrawColor(1, 1, 1)
+	for i, lines in ipairs(drawStack) do 
+		if #lines < 6 then
+			if(type(self.color) == "string") then
+				SetDrawColor(self.color)
+			elseif lines[1] then -- Don't color images
+				SetDrawColor(1,1,1)
 			else
 				SetDrawColor(unpack(self.color))
 			end
-			DrawImage(nil, ttX + 3, y - 1 + data.size / 2, ttW - 6, 2)
-			y = y + data.size + 2
+			DrawImage(unpack(lines))
+		else
+			DrawString(unpack(lines))
 		end
 	end
+	if type(self.color) == "string" then
+		SetDrawColor(self.color) 
+	else
+		SetDrawColor(unpack(self.color))
+	end
+	for i=0,columns do
+		DrawImage(nil, ttX + ttW * i - BORDER_WIDTH * math.ceil(i^2 / (i^2 + 1)), ttY, BORDER_WIDTH, maxColumnHeight) -- borders
+	end
+	DrawImage(nil, ttX, ttY, ttW * columns, BORDER_WIDTH) -- top border
+	DrawImage(nil, ttX, ttY + maxColumnHeight - BORDER_WIDTH, ttW * columns, BORDER_WIDTH) -- bottom border
+
 	return ttW, ttH
 end
\ No newline at end of file