When a failed request is sent, the "success" field is set to "false" and this causes the field is omitted from the JSON. The backed does not accept the message because the "success" field is missing though.

Updating to include fields in the JSON even when they are false.

lib/application_insights/channel/contracts/json_serializable.rb

@@ -41,7 +41,7 @@ module ApplicationInsights
         private
 
         def visit(object)
-          return unless object
+          return if object.nil?
 
           if object.is_a? Array
             object.map { |e| visit e }

test/application_insights/test_telemetry_client.rb

@@ -100,6 +100,16 @@ class TestTelemetryClient < Test::Unit::TestCase
     assert_equal expected, actual
   end
 
+  def test_track_request_view_works_as_expected_when_request_is_failed
+    client, sender = self.create_client
+    client.track_request 'test', '2015-01-24T23:10:22.7411910-08:00', '0:00:00:02.0000000','200', false
+    client.flush
+    expected = '[{"ver":1,"name":"Microsoft.ApplicationInsights.Request","time":"TIME_PLACEHOLDER","sampleRate":100.0,"tags":{"ai.internal.sdkVersion":"rb:__version__"},"data":{"baseType":"RequestData","baseData":{"ver":2,"id":"test","startTime":"2015-01-24T23:10:22.7411910-08:00","duration":"0:00:00:02.0000000","responseCode":"200","success":false}}}]'.gsub!(/__version__/, ApplicationInsights::VERSION)
+    sender.data_to_send[0].time = 'TIME_PLACEHOLDER'
+    actual = sender.data_to_send.to_json
+    assert_equal expected, actual
+  end
+
   def create_client
     sender = MockTelemetryClientSender.new
     queue = Channel::SynchronousQueue.new sender