diff --git a/extra_scripts/boost/boostNewLineIndentContinueMarkdownList.js b/extra_scripts/boost/boostNewLineIndentContinueMarkdownList.js
index aa766f6e..bc03e920 100644
--- a/extra_scripts/boost/boostNewLineIndentContinueMarkdownList.js
+++ b/extra_scripts/boost/boostNewLineIndentContinueMarkdownList.js
@@ -44,9 +44,46 @@
           ? match[2].replace('x', ' ')
           : (parseInt(match[3], 10) + 1) + match[4]
         replacements[i] = '\n' + indent + bullet + after
+
+        if (bullet) incrementRemainingMarkdownListNumbers(cm, pos)
       }
     }
-
     cm.replaceSelections(replacements)
   }
+  // Auto-updating Markdown list numbers when a new item is added to the
+  // middle of a list
+  function incrementRemainingMarkdownListNumbers(cm, pos) {
+    var startLine = pos.line, lookAhead = 0, skipCount = 0
+    var startItem = listRE.exec(cm.getLine(startLine)), startIndent = startItem[1]
+
+    do {
+      lookAhead += 1
+      var nextLineNumber = startLine + lookAhead
+      var nextLine = cm.getLine(nextLineNumber), nextItem = listRE.exec(nextLine)
+
+      if (nextItem) {
+        var nextIndent = nextItem[1]
+        var newNumber = (parseInt(startItem[3], 10) + lookAhead - skipCount)
+        var nextNumber = (parseInt(nextItem[3], 10)), itemNumber = nextNumber
+
+        if (startIndent === nextIndent && !isNaN(nextNumber)) {
+          if (newNumber === nextNumber) itemNumber = nextNumber + 1
+          if (newNumber > nextNumber) itemNumber = newNumber + 1
+          cm.replaceRange(
+            nextLine.replace(listRE, nextIndent + itemNumber + nextItem[4] + nextItem[5]),
+          {
+            line: nextLineNumber, ch: 0
+          }, {
+            line: nextLineNumber, ch: nextLine.length
+          })
+        } else {
+          if (startIndent.length > nextIndent.length) return
+          // This doesn't run if the next line immediatley indents, as it is
+          // not clear of the users intention (new indented item or same level)
+          if ((startIndent.length < nextIndent.length) && (lookAhead === 1)) return
+          skipCount += 1
+        }
+      }
+    } while (nextItem)
+  }
 })