diff --git a/src/static/js/ace2_inner.js b/src/static/js/ace2_inner.js
index 787aaaf94..44ac275e4 100644
--- a/src/static/js/ace2_inner.js
+++ b/src/static/js/ace2_inner.js
@@ -5166,6 +5166,16 @@ function Ace2Inner(){
       var t = '';
       var level = 0;
       var listType = /([a-z]+)([0-9]+)/.exec(getLineListType(n));
+
+      var togglineOn = false;
+
+      // Used to outdent if ol is removed
+      if(allLinesAreList){
+        togglingOn = false;
+      }else{
+        togglingOn = true;
+      }
+
       if (listType)
       {
         t = listType[1];
@@ -5173,12 +5183,25 @@ function Ace2Inner(){
       }
       var t = getLineListType(n);
 
-      // if already a list, deindent
-      if (allLinesAreList && level != 1) { level = level - 1;  }
-      // if already indented, then add a level of indentation to the list
-      else if (t && !allLinesAreList) { level = level + 1; }
+      if(t === listType) togglingOn = false;
+
+      if(togglingOn){
+        mods.push([n, allLinesAreList ? 'indent' + level : (t ? type + level : type + '1')]);
+      }
+
+      if(!togglingOn){
+        // scrap the entire indentation and list type
+        if(level === 1){ // if outdending but are the first item in the list then outdent
+          setLineListType(n, ''); // outdent
+        }
+        // else change to indented not bullet
+        if(level > 1){
+          setLineListType(n, ''); // remove bullet
+          let newLevel = level+1;
+          setLineListType(n, "indent"+level); // outdent
+        }
+      }
 
-      mods.push([n, allLinesAreList ? 'indent' + level : (t ? type + level : type + '1')]);
     }
 
     _.each(mods, function(mod){