diff --git a/TradeSkillMaster_Mailing/Modules/Inbox.lua b/TradeSkillMaster_Mailing/Modules/Inbox.lua
index 08e529b..ea812f1 100644
--- a/TradeSkillMaster_Mailing/Modules/Inbox.lua
+++ b/TradeSkillMaster_Mailing/Modules/Inbox.lua
@@ -499,6 +499,7 @@ function Inbox:CollectItems(items, callback)
 
 	local remaining = CopyTable(items)
 	local collected = false
+	local candidates = {}
 	for i = GetInboxNumItems(), 1, -1 do
 		local _, _, _, _, _, cod, _, hasItem = GetInboxHeaderInfo(i)
 		if hasItem and hasItem > 0 and (not cod or cod == 0) then
@@ -508,21 +509,42 @@ function Inbox:CollectItems(items, callback)
 				local need = itemString and remaining[itemString]
 				if need and need > 0 then
 					local quantity = select(3, GetInboxItem(i, j)) or 0
-					if quantity > 0 and (quantity <= need or not HasFittableStack(itemString, need)) then
-						if CanLootItem(itemString, quantity) then
-							TakeInboxItem(i, j)
-							remaining[itemString] = max(need - quantity, 0)
-							collected = true
-						elseif callback then
-							callback(L["Cannot finish auto looting, inventory is full or too many unique items."])
-							return
+					if quantity > 0 then
+						if not candidates[itemString] then
+							candidates[itemString] = {}
 						end
+						tinsert(candidates[itemString], { index = i, itemIndex = j, quantity = quantity })
 					end
 				end
 			end
 		end
 	end
 
+	for itemString, entries in pairs(candidates) do
+		table.sort(entries, function(a, b)
+			if a.quantity ~= b.quantity then
+				return a.quantity < b.quantity
+			end
+			return a.index > b.index
+		end)
+		for _, entry in ipairs(entries) do
+			local need = remaining[itemString]
+			if not need or need <= 0 then
+				break
+			end
+			if entry.quantity > 0 and (entry.quantity <= need or not HasFittableStack(itemString, need)) then
+				if CanLootItem(itemString, entry.quantity) then
+					TakeInboxItem(entry.index, entry.itemIndex)
+					remaining[itemString] = max(need - entry.quantity, 0)
+					collected = true
+				elseif callback then
+					callback(L["Cannot finish auto looting, inventory is full or too many unique items."])
+					return
+				end
+			end
+		end
+	end
+
 	-- Keep looting as new mail indexes shift, while preserving 1 free slot.
 	if collected then
 		TSMAPI:CreateTimeDelay("craftingGatherMailLoop", 0.4, function()