diff --git a/Src/xWorks/UploadToWebonaryController.cs b/Src/xWorks/UploadToWebonaryController.cs
index 7362a4760f..a396fe23d2 100644
--- a/Src/xWorks/UploadToWebonaryController.cs
+++ b/Src/xWorks/UploadToWebonaryController.cs
@@ -168,6 +168,8 @@ private bool RecursivelyPutFilesToWebonary(UploadToWebonaryModel model, string d
 				var signedUrl = PostContentToWebonary(model, webonaryView, "post/file", fileToSign);
 				if (string.IsNullOrEmpty(signedUrl))
 				{
+					webonaryView.SetStatusCondition(WebonaryStatusCondition.None);
+					webonaryView.UpdateStatus(xWorksStrings.UploadToWebonaryController_RetryAfterFailedConnection);
 					// Sleep briefly and try one more time (To compensate for a potential lambda cold start)
 					Thread.Sleep(500);
 					signedUrl = PostContentToWebonary(model, webonaryView, "post/file", fileToSign);
diff --git a/Src/xWorks/xWorksStrings.Designer.cs b/Src/xWorks/xWorksStrings.Designer.cs
index 8293acf139..7f5c7624d3 100644
--- a/Src/xWorks/xWorksStrings.Designer.cs
+++ b/Src/xWorks/xWorksStrings.Designer.cs
@@ -19,7 +19,7 @@ namespace SIL.FieldWorks.XWorks {
     // class via a tool like ResGen or Visual Studio.
     // To add or remove a member, edit your .ResX file then rerun ResGen
     // with the /str option, or rebuild your VS project.
-    [global::System.CodeDom.Compiler.GeneratedCodeAttribute("System.Resources.Tools.StronglyTypedResourceBuilder", "16.0.0.0")]
+    [global::System.CodeDom.Compiler.GeneratedCodeAttribute("System.Resources.Tools.StronglyTypedResourceBuilder", "17.0.0.0")]
     [global::System.Diagnostics.DebuggerNonUserCodeAttribute()]
     [global::System.Runtime.CompilerServices.CompilerGeneratedAttribute()]
     internal class xWorksStrings {
@@ -2980,6 +2980,15 @@ internal static string UploadToWebonaryController_ExportDictionaryContent_Export
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Initial Connection failed retrying....
+        /// </summary>
+        internal static string UploadToWebonaryController_RetryAfterFailedConnection {
+            get {
+                return ResourceManager.GetString("UploadToWebonaryController_RetryAfterFailedConnection", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to View.
         /// </summary>
diff --git a/Src/xWorks/xWorksStrings.resx b/Src/xWorks/xWorksStrings.resx
index 957e978a41..7b4dc3fee7 100644
--- a/Src/xWorks/xWorksStrings.resx
+++ b/Src/xWorks/xWorksStrings.resx
@@ -1259,4 +1259,7 @@ See USFM documentation for help.</value>
   <data name="Webonary_UnexpectedUploadError" xml:space="preserve">
     <value>Unexpected error encountered while uploading to webonary.</value>
   </data>
+  <data name="UploadToWebonaryController_RetryAfterFailedConnection" xml:space="preserve">
+    <value>Initial connection failed retrying...</value>
+  </data>
 </root>
\ No newline at end of file