diff --git a/app/models/blob.rb b/app/models/blob.rb
index 954d4e4d779..ad0bc2e2ead 100644
--- a/app/models/blob.rb
+++ b/app/models/blob.rb
@@ -156,7 +156,9 @@ class Blob < SimpleDelegator
   end
 
   def file_type
-    Gitlab::FileDetector.type_of(path)
+    name = File.basename(path)
+
+    Gitlab::FileDetector.type_of(path) || Gitlab::FileDetector.type_of(name)
   end
 
   def video?
diff --git a/lib/gitlab/file_detector.rb b/lib/gitlab/file_detector.rb
index a8cb7fc3fe7..1fa1399c531 100644
--- a/lib/gitlab/file_detector.rb
+++ b/lib/gitlab/file_detector.rb
@@ -6,10 +6,10 @@ module Gitlab
   module FileDetector
     PATTERNS = {
       # Project files
-      readme: /\Areadme/i,
-      changelog: /\A(changelog|history|changes|news)/i,
-      license: /\A(licen[sc]e|copying)(\..+|\z)/i,
-      contributing: /\Acontributing/i,
+      readme: /\Areadme[^\/]*\z/i,
+      changelog: /\A(changelog|history|changes|news)[^\/]*\z/i,
+      license: /\A(licen[sc]e|copying)(\.[^\/]+)?\z/i,
+      contributing: /\Acontributing[^\/]*\z/i,
       version: 'version',
       avatar: /\Alogo\.(png|jpg|gif)\z/,
 
@@ -17,20 +17,20 @@ module Gitlab
       gitignore: '.gitignore',
       koding: '.koding.yml',
       gitlab_ci: '.gitlab-ci.yml',
-      route_map: 'route-map.yml',
+      route_map: '.gitlab/route-map.yml',
 
       # Dependency files
-      cartfile: /\ACartfile/,
+      cartfile: /\ACartfile[^\/]*\z/,
       composer_json: 'composer.json',
       gemfile: /\A(Gemfile|gems\.rb)\z/,
       gemfile_lock: 'Gemfile.lock',
-      gemspec: /\.gemspec\z/,
+      gemspec: /\A[^\/]*\.gemspec\z/,
       godeps_json: 'Godeps.json',
       package_json: 'package.json',
       podfile: 'Podfile',
-      podspec_json: /\.podspec\.json\z/,
-      podspec: /\.podspec\z/,
-      requirements_txt: /requirements\.txt\z/,
+      podspec_json: /\A[^\/]*\.podspec\.json\z/,
+      podspec: /\A[^\/]*\.podspec\z/,
+      requirements_txt: /\A[^\/]*requirements\.txt\z/,
       yarn_lock: 'yarn.lock'
     }.freeze
 
@@ -63,13 +63,11 @@ module Gitlab
     #     type_of('README.md') # => :readme
     #     type_of('VERSION') # => :version
     def self.type_of(path)
-      name = File.basename(path)
-
       PATTERNS.each do |type, search|
         did_match = if search.is_a?(Regexp)
-                      name =~ search
+                      path =~ search
                     else
-                      name.casecmp(search) == 0
+                      path.casecmp(search) == 0
                     end
 
         return type if did_match
diff --git a/spec/lib/gitlab/file_detector_spec.rb b/spec/lib/gitlab/file_detector_spec.rb
index 695fd6f8573..b5ac07c94fa 100644
--- a/spec/lib/gitlab/file_detector_spec.rb
+++ b/spec/lib/gitlab/file_detector_spec.rb
@@ -18,6 +18,10 @@ describe Gitlab::FileDetector do
       expect(described_class.type_of('README.md')).to eq(:readme)
     end
 
+    it 'returns nil for a README file in a directory' do
+      expect(described_class.type_of('foo/README.md')).to be_nil
+    end
+
     it 'returns the type of a changelog file' do
       %w(CHANGELOG HISTORY CHANGES NEWS).each do |file|
         expect(described_class.type_of(file)).to eq(:changelog)