diff --git a/lib/webrat/core/elements/field.rb b/lib/webrat/core/elements/field.rb
index 49c042c..8d8afc2 100644
--- a/lib/webrat/core/elements/field.rb
+++ b/lib/webrat/core/elements/field.rb
@@ -366,6 +366,8 @@ module Webrat
       when :merb
         # TODO: support content_type
         File.new(@value)
+      when :rack
+        Rack::Test::UploadedFile.new(@value, content_type)
       end
     end
 
diff --git a/spec/integration/rack/app.rb b/spec/integration/rack/app.rb
index 61ab332..0e863a4 100644
--- a/spec/integration/rack/app.rb
+++ b/spec/integration/rack/app.rb
@@ -33,6 +33,14 @@ class RackApp < Sinatra::Base
     @email = params[:email]
     erb :hello
   end
+
+  get "/upload" do
+    erb :uploader
+  end
+
+  post "/upload" do
+    params[:uploaded_file].to_yaml
+  end
 end
 
 __END__
@@ -71,3 +79,11 @@ __END__
 @@ hello
 <p>Hello, <%= @user %></p>
 <p>Your email is: <%= @email %></p>
+
+@@ uploader
+<form action="/upload" method="post">
+  <label>
+    File <input type="file" name="uploaded_file" />
+  </label>
+  <input type="submit" value="Upload">
+</form>
diff --git a/spec/integration/rack/test/webrat_rack_test.rb b/spec/integration/rack/test/webrat_rack_test.rb
index ebe2d3f..ec82973 100644
--- a/spec/integration/rack/test/webrat_rack_test.rb
+++ b/spec/integration/rack/test/webrat_rack_test.rb
@@ -46,6 +46,17 @@ class WebratRackTest < Test::Unit::TestCase
     visit "/absolute_redirect"
     assert_contain "spam"
   end
+
+  def test_upload_file
+    visit "/upload"
+    attach_file "File", __FILE__, "text/ruby"
+    click_button "Upload"
+
+    upload = YAML.load(response_body)
+    assert_equal "text/ruby", upload[:type]
+    assert_equal "webrat_rack_test.rb", upload[:filename]
+    assert upload[:tempfile].respond_to?(:read)
+  end
 end
 
 class WebratRackSetupTest < Test::Unit::TestCase