diff --git a/app/uk/gov/hmrc/apiplatformoutboundsoap/connectors/OutboundConnector.scala b/app/uk/gov/hmrc/apiplatformoutboundsoap/connectors/OutboundConnector.scala
index cfd6159..7347db2 100644
--- a/app/uk/gov/hmrc/apiplatformoutboundsoap/connectors/OutboundConnector.scala
+++ b/app/uk/gov/hmrc/apiplatformoutboundsoap/connectors/OutboundConnector.scala
@@ -26,7 +26,8 @@ import javax.inject.{Inject, Singleton}
 import scala.concurrent.{ExecutionContext, Future}
 
 @Singleton
-class OutboundConnector @Inject()(appConfig: AppConfig, httpClient: HttpClient)(implicit ec: ExecutionContext) {
+class OutboundConnector @Inject()(appConfig: AppConfig, httpClient: HttpClient)
+                                 (implicit ec: ExecutionContext) extends HttpErrorFunctions {
 
   val logger: LoggerLike = Logger
 
@@ -34,7 +35,7 @@ class OutboundConnector @Inject()(appConfig: AppConfig, httpClient: HttpClient)(
     implicit val hc: HeaderCarrier =  HeaderCarrier().withExtraHeaders(CONTENT_TYPE -> "application/soap+xml")
 
     httpClient.POSTString[HttpResponse](appConfig.ccn2Url, message) map { response =>
-      if (response.status >= 400) {
+      if (!is2xx(response.status)) {
         logger.warn(s"Attempted request to ${appConfig.ccn2Url} responded with HTTP response code ${response.status}")
       }
       response.status
diff --git a/app/uk/gov/hmrc/apiplatformoutboundsoap/services/OutboundService.scala b/app/uk/gov/hmrc/apiplatformoutboundsoap/services/OutboundService.scala
index 209ec2f..919fa31 100644
--- a/app/uk/gov/hmrc/apiplatformoutboundsoap/services/OutboundService.scala
+++ b/app/uk/gov/hmrc/apiplatformoutboundsoap/services/OutboundService.scala
@@ -60,11 +60,14 @@ class OutboundService @Inject()(outboundConnector: OutboundConnector,
   def sendMessage(message: MessageRequest): Future[OutboundSoapMessage] = {
     val envelope = buildEnvelope(message)
     outboundConnector.postMessage(envelope) flatMap { result =>
+      val globalId: UUID = randomUUID
       val messageId = message.addressing.flatMap(_.messageId)
       val outboundSoapMessage = if (is2xx(result)) {
-        SentOutboundSoapMessage(randomUUID, messageId, envelope, now)
+        logger.info(s"Message with global ID $globalId and message ID $messageId successfully sent")
+        SentOutboundSoapMessage(globalId, messageId, envelope, now)
       } else {
-        RetryingOutboundSoapMessage(randomUUID, messageId, envelope, now, now.plus(appConfig.retryInterval.toMillis))
+        logger.info(s"Message with global ID $globalId and message ID $messageId failed on first attempt")
+        RetryingOutboundSoapMessage(globalId, messageId, envelope, now, now.plus(appConfig.retryInterval.toMillis))
       }
       outboundMessageRepository.persist(outboundSoapMessage).map(_ => outboundSoapMessage)
     }
@@ -78,17 +81,20 @@ class OutboundService @Inject()(outboundConnector: OutboundConnector,
     val nextRetryDateTime: DateTime = now.plus(appConfig.retryInterval.toMillis)
     outboundConnector.postMessage(message.soapMessage) flatMap { result =>
       if (is2xx(result)) {
+        logger.info(s"Retrying message with global ID ${message.globalId} and message ID ${message.messageId} succeeded")
         outboundMessageRepository.updateStatus(message.globalId, SendingStatus.SENT) map { updatedMessage =>
           updatedMessage.map(notificationCallbackConnector.sendNotification)
           ()
         }
       } else {
         if (message.createDateTime.plus(appConfig.retryDuration.toMillis).isBefore(now.getMillis)){
+          logger.info(s"Retrying message with global ID ${message.globalId} and message ID ${message.messageId} failed on last attempt")
           outboundMessageRepository.updateStatus(message.globalId, SendingStatus.FAILED).map { updatedMessage =>
             updatedMessage.map(notificationCallbackConnector.sendNotification)
             ()
           }
         } else{
+          logger.info(s"Retrying message with global ID ${message.globalId} and message ID ${message.messageId} failed")
           outboundMessageRepository.updateNextRetryTime(message.globalId, nextRetryDateTime).map(_ => ())
         }
       }