diff --git a/spec/app/syntax-spec.coffee b/spec/app/syntax-spec.coffee
index 50917c30c..497bb88ff 100644
--- a/spec/app/syntax-spec.coffee
+++ b/spec/app/syntax-spec.coffee
@@ -1,4 +1,5 @@
 fsUtils = require 'fs-utils'
+TextMateGrammar = require 'text-mate-grammar'
 
 describe "the `syntax` global", ->
   beforeEach ->
@@ -57,6 +58,23 @@ describe "the `syntax` global", ->
       syntax.clearGrammarOverrideForPath(path)
       expect(syntax.selectGrammar(path).name).not.toBe 'Ruby'
 
+    describe "when multiple grammars have matching fileTypes", ->
+      it "selects the grammar with the longest fileType match", ->
+        grammar1 = new TextMateGrammar
+          name: 'test1'
+          scopeName: 'source1'
+          fileTypes: ['test', 'more.test']
+
+        grammar2 = new TextMateGrammar
+          name: 'test2'
+          scopeName: 'source2'
+          fileTypes: ['test']
+
+        syntax.addGrammar(grammar1)
+        syntax.addGrammar(grammar2)
+
+        expect(syntax.selectGrammar('more.test', '')).toBe grammar1
+
   describe ".removeGrammar(grammar)", ->
     it "removes the grammar, so it won't be returned by selectGrammar", ->
       grammar = syntax.selectGrammar('foo.js')
diff --git a/src/app/text-mate-grammar.coffee b/src/app/text-mate-grammar.coffee
index f86435026..5796631b0 100644
--- a/src/app/text-mate-grammar.coffee
+++ b/src/app/text-mate-grammar.coffee
@@ -74,14 +74,13 @@ class TextMateGrammar
   getScore: (filePath, contents) ->
     contents = fsUtils.read(filePath) if not contents? and fsUtils.isFileSync(filePath)
 
+
     if syntax.grammarOverrideForPath(filePath) is @scopeName
-      3
+      2 + filePath.length
     else if @matchesContents(contents)
-      2
-    else if @matchesPath(filePath)
-      1
+      1 + filePath.length
     else
-      -1
+      @getPathScore(filePath)
 
   matchesContents: (contents) ->
     return false unless contents? and @firstLineRegex?
@@ -100,13 +99,18 @@ class TextMateGrammar
     lines = contents.split('\n')
     @firstLineRegex.test(lines[0..numberOfNewlinesInRegex].join('\n'))
 
-  matchesPath: (filePath) ->
-    return false unless filePath?
+  getPathScore: (filePath) ->
+    return -1 unless filePath?
+
     pathComponents = filePath.split(pathSplitRegex)
-    _.find @fileTypes, (fileType) ->
+    pathScore = -1
+    @fileTypes.forEach (fileType) ->
       fileTypeComponents = fileType.split(pathSplitRegex)
       pathSuffix = pathComponents[-fileTypeComponents.length..-1]
-      _.isEqual(pathSuffix, fileTypeComponents)
+      if _.isEqual(pathSuffix, fileTypeComponents)
+        pathScore = Math.max(pathScore, fileType.length)
+
+    pathScore
 
   tokenizeLine: (line, ruleStack=[@getInitialRule()], firstLine=false) ->
     originalRuleStack = ruleStack