diff --git a/Meadow.CLI.Core/Devices/MeadowLocalDevice.Comms.cs b/Meadow.CLI.Core/Devices/MeadowLocalDevice.Comms.cs
index 98eedeb0..34a79bd2 100644
--- a/Meadow.CLI.Core/Devices/MeadowLocalDevice.Comms.cs
+++ b/Meadow.CLI.Core/Devices/MeadowLocalDevice.Comms.cs
@@ -16,6 +16,8 @@ public partial class MeadowLocalDevice
         private const int PROGESS_INCREMENTS = 5;
         uint _packetCrc32;
         private readonly SemaphoreSlim _comPortSemaphore = new SemaphoreSlim(1, 1);
+        bool reUploadSkippedFiles = false;
+        byte reUploadCounter = 0;
 
         public async Task SendTheEntireFile(FileCommand command,
                                             bool lastInSeries,
@@ -364,6 +366,10 @@ void ResponseHandler(object s, MeadowMessageEventArgs e)
                             Logger?.LogError(msg);
                         }
                         break;
+                    case MeadowMessageType.DownloadFailed:
+                        // Set Re-download flag, increment download count.
+                        reUploadSkippedFiles = true;
+                        break;
                     default:
                         break;
                 }
diff --git a/Meadow.CLI.Core/Devices/MeadowLocalDevice.FileManager.cs b/Meadow.CLI.Core/Devices/MeadowLocalDevice.FileManager.cs
index effa7455..7debc9b2 100644
--- a/Meadow.CLI.Core/Devices/MeadowLocalDevice.FileManager.cs
+++ b/Meadow.CLI.Core/Devices/MeadowLocalDevice.FileManager.cs
@@ -736,7 +736,32 @@ await WriteFile(
                             cancellationToken);
                 }
 
-                Logger.LogInformation($"{Environment.NewLine}{fi.Name} deploy complete!{Environment.NewLine}");
+                if (reUploadSkippedFiles)
+                {
+                    reUploadCounter++;
+                    if (reUploadCounter < 3)
+                    {
+                        await DeployApp(applicationFilePath,
+                            osVersion,
+                            includePdbs,
+                            verbose,
+                            noLink,
+                            cancellationToken);
+                    }
+                    else
+                    {
+                        // Clean up the reload variables.
+                        reUploadSkippedFiles = false;
+                        reUploadCounter = 0;
+
+                        // Let's bail out of here
+                        throw new Exception("Tried to send files to Meadow at least 3 times and failed. Something it seriously wrong! Check you are running the latest OS etc.");
+                    }
+                }
+                else
+                {
+                    Logger.LogInformation($"{Environment.NewLine}{fi.Name} deploy complete!{Environment.NewLine}");
+                }
             }
             catch (Exception ex)
             {
diff --git a/Meadow.CLI.Core/Internals/MeadowCommunication/MeadowSerialDataProcessor.cs b/Meadow.CLI.Core/Internals/MeadowCommunication/MeadowSerialDataProcessor.cs
index 40db55a9..38075904 100644
--- a/Meadow.CLI.Core/Internals/MeadowCommunication/MeadowSerialDataProcessor.cs
+++ b/Meadow.CLI.Core/Internals/MeadowCommunication/MeadowSerialDataProcessor.cs
@@ -33,6 +33,7 @@ public enum MeadowMessageType
         Concluded,
         DownloadStartOkay,
         DownloadStartFail,
+        DownloadFailed,
         DevicePublicKey
     }
 
@@ -364,6 +365,11 @@ private void ParseAndProcessReceivedPacket(byte[] receivedMsg, CancellationToken
 
                                 break;
                             }
+
+                        case HcomHostRequestType.HCOM_HOST_REQUEST_DNLD_FAIL_RESEND:
+                            OnReceiveData?.Invoke(this, new MeadowMessageEventArgs(MeadowMessageType.DownloadFailed, responseString));
+                            break;
+
                         case HcomHostRequestType.HCOM_HOST_REQUEST_DEVICE_PUBLIC_KEY:
                             OnReceiveData?.Invoke(this, new MeadowMessageEventArgs(MeadowMessageType.DevicePublicKey, responseString));
                             break;
diff --git a/Meadow.CLI.Core/Internals/MeadowCommunication/ReceiveClasses/ReceiveMessageFactoryManager.cs b/Meadow.CLI.Core/Internals/MeadowCommunication/ReceiveClasses/ReceiveMessageFactoryManager.cs
index 38b3ca29..86dd1ec4 100644
--- a/Meadow.CLI.Core/Internals/MeadowCommunication/ReceiveClasses/ReceiveMessageFactoryManager.cs
+++ b/Meadow.CLI.Core/Internals/MeadowCommunication/ReceiveClasses/ReceiveMessageFactoryManager.cs
@@ -31,6 +31,7 @@ public ReceiveMessageFactoryManager(ILogger logger)
                 {HcomHostRequestType.HCOM_HOST_REQUEST_TEXT_MONO_STDERR, new ReceiveSimpleTextFactory() },
                 {HcomHostRequestType.HCOM_HOST_REQUEST_FILE_START_OKAY, new ReceiveSimpleTextFactory() },
                 {HcomHostRequestType.HCOM_HOST_REQUEST_FILE_START_FAIL, new ReceiveSimpleTextFactory() },
+                {HcomHostRequestType.HCOM_HOST_REQUEST_DNLD_FAIL_RESEND, new ReceiveSimpleTextFactory()},
                 {HcomHostRequestType.HCOM_HOST_REQUEST_DEVICE_PUBLIC_KEY, new ReceiveSimpleTextFactory()},
             };
         }
diff --git a/Meadow.Hcom/HcomHostRequestType.cs b/Meadow.Hcom/HcomHostRequestType.cs
index 906e5b4b..fec2a5bd 100644
--- a/Meadow.Hcom/HcomHostRequestType.cs
+++ b/Meadow.Hcom/HcomHostRequestType.cs
@@ -23,6 +23,10 @@ public enum HcomHostRequestType : ushort
         HCOM_HOST_REQUEST_TEXT_MONO_STDERR = 0x0d | HcomProtocolHeaderTypes.HCOM_PROTOCOL_HEADER_TYPE_SIMPLE_TEXT,
         HCOM_HOST_REQUEST_FILE_START_OKAY = 0x0e | HcomProtocolHeaderTypes.HCOM_PROTOCOL_HEADER_TYPE_SIMPLE_TEXT,
         HCOM_HOST_REQUEST_FILE_START_FAIL = 0x0f | HcomProtocolHeaderTypes.HCOM_PROTOCOL_HEADER_TYPE_SIMPLE_TEXT,
+
+        // The Meadow file name is enclosed in single quotes 'filename' and CLI will
+        // need to workout what file was being downloaded and start the download over
+        HCOM_HOST_REQUEST_DNLD_FAIL_RESEND = 0x12 | HcomProtocolHeaderTypes.HCOM_PROTOCOL_HEADER_TYPE_SIMPLE_TEXT,
         HCOM_HOST_REQUEST_DEVICE_PUBLIC_KEY = 0x13 | HcomProtocolHeaderTypes.HCOM_PROTOCOL_HEADER_TYPE_SIMPLE_TEXT,
 
         // Simple with debugger message from Meadow