diff --git a/Items Properties/graysonsolis_Toggle grouping.lua b/Items Properties/graysonsolis_Toggle grouping.lua
new file mode 100644
index 000000000..a0ef27a76
--- /dev/null
+++ b/Items Properties/graysonsolis_Toggle grouping.lua	
@@ -0,0 +1,60 @@
+-- @description Toggle grouping
+-- @author Grayson Solis
+-- @version 1.0
+-- @screenshot Example: https://imgur.com/flmEK6P
+-- @about
+--   TOGGLE GROUPING BEHAVIOR:
+--
+--   If you select:
+--       - One grouped item -> Ungroups it
+--       - One ungrouped item -> Does nothing
+--       - All ungrouped items -> it groups them together.
+--       - All grouped items (same group or not) -> it ungroups them.
+--       - A mix of grouped and ungrouped items -> it adds the ungrouped ones to the existing group.
+
+function GetNextGroupID()
+    local max_id = 0
+    local item_count = reaper.CountMediaItems(0)
+    for i = 0, item_count - 1 do
+        local item = reaper.GetMediaItem(0, i)
+        local group_id = reaper.GetMediaItemInfo_Value(item, "I_GROUPID")
+        if group_id > max_id then
+            max_id = group_id
+        end
+    end
+    return max_id + 1
+end
+
+reaper.Undo_BeginBlock()
+local sel_count = reaper.CountSelectedMediaItems(0)
+if sel_count == 0 then return end
+if sel_count == 1 and reaper.GetMediaItemInfo_Value(reaper.GetSelectedMediaItem(0, 0), "I_GROUPID") == 0 then return end 
+local group_id = nil             
+local has_grouped = false        
+local has_ungrouped = false   
+for i = 0, sel_count - 1 do
+    local item = reaper.GetSelectedMediaItem(0, i)
+    local id = reaper.GetMediaItemInfo_Value(item, "I_GROUPID")
+    if id > 0 then
+        has_grouped = true
+        group_id = group_id or id
+    else
+        has_ungrouped = true
+    end
+end
+if has_grouped and has_ungrouped then
+    for i = 0, sel_count - 1 do
+        reaper.SetMediaItemInfo_Value(reaper.GetSelectedMediaItem(0, i), "I_GROUPID", group_id)
+    end
+elseif has_grouped and not has_ungrouped then
+    for i = 0, sel_count - 1 do
+        reaper.SetMediaItemInfo_Value(reaper.GetSelectedMediaItem(0, i), "I_GROUPID", 0)
+    end
+else
+    local new_id = GetNextGroupID()
+    for i = 0, sel_count - 1 do
+        reaper.SetMediaItemInfo_Value(reaper.GetSelectedMediaItem(0, i), "I_GROUPID", new_id)
+    end
+end
+reaper.UpdateArrange()
+reaper.Undo_EndBlock("Toggle grouping", -1)