diff --git a/source/Meadow.Core/MeadowCloudService.cs b/source/Meadow.Core/MeadowCloudService.cs
index 93556f23..b54c8ff0 100644
--- a/source/Meadow.Core/MeadowCloudService.cs
+++ b/source/Meadow.Core/MeadowCloudService.cs
@@ -177,7 +177,14 @@ private async Task<bool> Send<T>(T item, string endpoint)
 
         if (CurrentJwt == null)
         {
-            await Authenticate();
+            if (!await Authenticate())
+            {
+                errorMessage = $"Cloud auth failed before sending";
+                ServiceError?.Invoke(this, errorMessage);
+                Resolver.Log.Warn(errorMessage);
+                // TODO: should we retry after this?
+                return false;
+            }
         }
 
         using (HttpClient client = new HttpClient())
@@ -208,7 +215,7 @@ private async Task<bool> Send<T>(T item, string endpoint)
 
             if (response.IsSuccessStatusCode)
             {
-                Resolver.Log.Debug("cloud log success");
+                Resolver.Log.Debug("cloud send success");
                 result = true;
             }
             else if (response.StatusCode == HttpStatusCode.Unauthorized)
@@ -217,6 +224,7 @@ private async Task<bool> Send<T>(T item, string endpoint)
                 {
                     attempt++;
                     Resolver.Log.Debug($"Unauthorized, re-authenticating");
+                    // by setting this to null and retrying, Authenticate will get called
                     CurrentJwt = null;
                     goto retry;
                 }
@@ -276,7 +284,7 @@ private async Task<bool> Send<T>(T item, string endpoint)
                 return pkFileContent;
             }
         }
-        else if(SRI.RuntimeInformation.IsOSPlatform(OSPlatform.OSX))
+        else if (SRI.RuntimeInformation.IsOSPlatform(OSPlatform.OSX))
         {
             var sshFolder = new DirectoryInfo(Path.Combine(Environment.GetFolderPath(Environment.SpecialFolder.UserProfile), ".ssh"));