diff --git a/spec/app/language-mode-spec.coffee b/spec/app/language-mode-spec.coffee
index c851eb77f..0904451f0 100644
--- a/spec/app/language-mode-spec.coffee
+++ b/spec/app/language-mode-spec.coffee
@@ -19,11 +19,16 @@ describe "LanguageMode", ->
         expect(jsEditSession.languageMode.grammar.name).toBe "JavaScript"
         jsEditSession.destroy()
 
-    describe "matching character insertion", ->
+    describe "bracket insertion", ->
       beforeEach ->
         editSession.buffer.setText("")
 
-      describe "when there is non-whitespace after the cursor", ->
+      describe "when more than one charachter is inserted", ->
+        it "does not insert a matching bracket", ->
+          editSession.insertText("woah(")
+          expect(editSession.buffer.getText()).toBe "woah("
+
+      describe "when there is a word charachter after the cursor", ->
         it "does not insert a matching bracket", ->
           editSession.buffer.setText("ab")
           editSession.setCursorBufferPosition([0, 1])
@@ -42,38 +47,94 @@ describe "LanguageMode", ->
 
           expect(editSession.buffer.getText()).toBe "())\na)b\n[)]\n1)2"
 
-      describe "when ( is inserted", ->
-        it "inserts a matching ) following the cursor", ->
-          editSession.insertText '('
-          expect(buffer.lineForRow(0)).toMatch /^\(\)/
-
-      describe "when [ is inserted", ->
-        it "inserts a matching ] following the cursor", ->
-          editSession.insertText '['
-          expect(buffer.lineForRow(0)).toMatch /^\[\]/
-
-      describe "when { is inserted", ->
-        it "inserts a matching ) following the cursor", ->
+      describe "when there is a non-word characher after the cursor", ->
+        it "inserts a closing bracket after an opening bracket is inserted", ->
+          editSession.buffer.setText("}")
+          editSession.setCursorBufferPosition([0, 0])
           editSession.insertText '{'
-          expect(buffer.lineForRow(0)).toMatch /^\{\}/
+          expect(buffer.lineForRow(0)).toBe "{}}"
+          expect(editSession.getCursorBufferPosition()).toEqual([0,1])
 
-      describe "when \" is inserted", ->
-        it "inserts a matching \" following the cursor", ->
+      describe "when the cursor is at the end of the line", ->
+        it "inserts a closing bracket after an opening bracket is inserted", ->
+          editSession.buffer.setText("")
+          editSession.insertText '{'
+          expect(buffer.lineForRow(0)).toBe "{}"
+          expect(editSession.getCursorBufferPosition()).toEqual([0,1])
+
+          editSession.buffer.setText("")
+          editSession.insertText '('
+          expect(buffer.lineForRow(0)).toBe "()"
+          expect(editSession.getCursorBufferPosition()).toEqual([0,1])
+
+          editSession.buffer.setText("")
+          editSession.insertText '['
+          expect(buffer.lineForRow(0)).toBe "[]"
+          expect(editSession.getCursorBufferPosition()).toEqual([0,1])
+
+          editSession.buffer.setText("")
           editSession.insertText '"'
-          expect(buffer.lineForRow(0)).toMatch /^""/
+          expect(buffer.lineForRow(0)).toBe '""'
+          expect(editSession.getCursorBufferPosition()).toEqual([0,1])
 
-      describe "when ' is inserted", ->
-        it "inserts a matching ' following the cursor", ->
+          editSession.buffer.setText("")
           editSession.insertText "'"
-          expect(buffer.lineForRow(0)).toMatch /^''/
+          expect(buffer.lineForRow(0)).toBe "''"
+          expect(editSession.getCursorBufferPosition()).toEqual([0,1])
 
-      describe "when ) is inserted before a )", ->
-        it "moves the cursor one column to the right instead of inserting a new )", ->
-          editSession.insertText '() '
-          editSession.setCursorBufferPosition([0, 1])
-          editSession.insertText ')'
-          expect(buffer.lineForRow(0)).toBe "() "
-          expect(editSession.getCursorBufferPosition().column).toBe 2
+      describe "when the cursor is on a closing bracket and a closing bracket is inserted", ->
+        describe "when the closing bracket was there previously", ->
+          it "inserts a closing bracket", ->
+            editSession.insertText '()x'
+            editSession.setCursorBufferPosition([0, 1])
+            editSession.insertText ')'
+            expect(buffer.lineForRow(0)).toBe "())x"
+            expect(editSession.getCursorBufferPosition().column).toBe 2
+
+        describe "when the closing bracket was automatically inserted from inserting an opening bracket", ->
+          it "only moves cursor over the closing bracket one time", ->
+            editSession.insertText '('
+            expect(buffer.lineForRow(0)).toBe "()"
+            editSession.setCursorBufferPosition([0, 1])
+            editSession.insertText ')'
+            expect(buffer.lineForRow(0)).toBe "()"
+            expect(editSession.getCursorBufferPosition()).toEqual [0, 2]
+
+            editSession.setCursorBufferPosition([0, 1])
+            editSession.insertText ')'
+            expect(buffer.lineForRow(0)).toBe "())"
+            expect(editSession.getCursorBufferPosition()).toEqual [0, 2]
+
+          it "moves cursor over the closing bracket after other text is inserted", ->
+            editSession.insertText '('
+            editSession.insertText 'ok cool'
+            expect(buffer.lineForRow(0)).toBe "(ok cool)"
+            editSession.setCursorBufferPosition([0, 8])
+            editSession.insertText ')'
+            expect(buffer.lineForRow(0)).toBe "(ok cool)"
+            expect(editSession.getCursorBufferPosition()).toEqual [0, 9]
+
+          it "works with nested brackets", ->
+            editSession.insertText '('
+            editSession.insertText '1'
+            editSession.insertText '('
+            editSession.insertText '2'
+            expect(buffer.lineForRow(0)).toBe "(1(2))"
+            editSession.setCursorBufferPosition([0, 4])
+            editSession.insertText ')'
+            expect(buffer.lineForRow(0)).toBe "(1(2))"
+            expect(editSession.getCursorBufferPosition()).toEqual [0, 5]
+            editSession.insertText ')'
+            expect(buffer.lineForRow(0)).toBe "(1(2))"
+            expect(editSession.getCursorBufferPosition()).toEqual [0, 6]
+
+          it "works with mixed brackets", ->
+            editSession.insertText '('
+            editSession.insertText '}'
+            expect(buffer.lineForRow(0)).toBe "(})"
+            editSession.insertText ')'
+            expect(buffer.lineForRow(0)).toBe "(})"
+            expect(editSession.getCursorBufferPosition()).toEqual [0, 3]
 
   describe "javascript", ->
     beforeEach ->
diff --git a/src/app/language-mode.coffee b/src/app/language-mode.coffee
index 127f3f050..f66d3f366 100644
--- a/src/app/language-mode.coffee
+++ b/src/app/language-mode.coffee
@@ -15,20 +15,29 @@ class LanguageMode
   constructor: (@editSession) ->
     @buffer = @editSession.buffer
     @grammar = TextMateBundle.grammarForFileName(@buffer.getBaseName())
+    @bracketAnchorRanges = []
 
     _.adviseBefore @editSession, 'insertText', (text) =>
       return true if @editSession.hasMultipleCursors()
 
       cursorBufferPosition = @editSession.getCursorBufferPosition()
-      nextCharacter = @editSession.getTextInBufferRange([cursorBufferPosition, cursorBufferPosition.add([0, 1])])
+      nextCharachter = @editSession.getTextInBufferRange([cursorBufferPosition, cursorBufferPosition.add([0,1])])
 
-      if @isClosingBracket(text) and text == nextCharacter
-        @editSession.moveCursorRight()
-        false
-      else if /^\s*$/.test(nextCharacter) and pairedCharacter = @pairedCharacters[text]
-        @editSession.insertText text + pairedCharacter
+      if @isOpeningBracket(text) and /\W|^$/.test(nextCharachter)
+        @editSession.insertText(text + @pairedCharacters[text])
         @editSession.moveCursorLeft()
+        range = [cursorBufferPosition, cursorBufferPosition.add([0, text.length])]
+        @bracketAnchorRanges.push @editSession.addAnchorRange(range)
         false
+      else if @isClosingBracket(text)
+        return true if nextCharachter != text
+        anchorRange = @bracketAnchorRanges.filter((anchorRange) -> anchorRange.getBufferRange().end.isEqual(cursorBufferPosition))[0]
+
+        if anchorRange
+          anchorRange.destroy()
+          @bracketAnchorRanges = _.without(@bracketAnchorRanges, anchorRange)
+          @editSession.moveCursorRight()
+          false
 
   isOpeningBracket: (string) ->
     @pairedCharacters[string]?