diff --git a/AstarteDeviceSDKCSharp/Data/AstarteFailedMessageStorage.cs b/AstarteDeviceSDKCSharp/Data/AstarteFailedMessageStorage.cs
index a167368..1c11fdc 100644
--- a/AstarteDeviceSDKCSharp/Data/AstarteFailedMessageStorage.cs
+++ b/AstarteDeviceSDKCSharp/Data/AstarteFailedMessageStorage.cs
@@ -106,5 +106,41 @@ public void RejectFirst()
 
             _astarteDbContext.SaveChanges();
         }
+
+        public bool IsCacheEmpty()
+        {
+            return !_astarteFailedMessageVolatile.Any();
+        }
+
+        public AstarteFailedMessageEntry? PeekFirstCache()
+        {
+            return _astarteFailedMessageVolatile
+            .OrderBy(x => x.Id)
+            .FirstOrDefault();
+        }
+
+        public void RejectFirstCache()
+        {
+            var failedMessages = _astarteFailedMessageVolatile
+            .OrderBy(x => x.Id)
+            .ToList();
+
+            if (failedMessages.Count() > 0)
+            {
+                _astarteDbContext.AstarteFailedMessages.Remove(failedMessages.First());
+            }
+        }
+
+        public void AckFirstCache()
+        {
+            var failedMessages = _astarteFailedMessageVolatile
+            .OrderBy(x => x.Id)
+            .ToList();
+
+            if (failedMessages.Count() > 0)
+            {
+                _astarteFailedMessageVolatile.Remove(failedMessages.First());
+            }
+        }
     }
 }
diff --git a/AstarteDeviceSDKCSharp/Data/IAstarteFailedMessageStorage.cs b/AstarteDeviceSDKCSharp/Data/IAstarteFailedMessageStorage.cs
index 7be777f..c34f094 100644
--- a/AstarteDeviceSDKCSharp/Data/IAstarteFailedMessageStorage.cs
+++ b/AstarteDeviceSDKCSharp/Data/IAstarteFailedMessageStorage.cs
@@ -32,10 +32,18 @@ public interface IAstarteFailedMessageStorage
 
         bool IsEmpty();
 
+        bool IsCacheEmpty();
+
         AstarteFailedMessageEntry? PeekFirst();
 
+        AstarteFailedMessageEntry? PeekFirstCache();
+
         void AckFirst();
 
+        void AckFirstCache();
+
         void RejectFirst();
+
+        void RejectFirstCache();
     }
 }
diff --git a/AstarteDeviceSDKCSharp/Transport/MQTT/AstarteMqttV1Transport.cs b/AstarteDeviceSDKCSharp/Transport/MQTT/AstarteMqttV1Transport.cs
index 6d0c41f..c8bd8ee 100644
--- a/AstarteDeviceSDKCSharp/Transport/MQTT/AstarteMqttV1Transport.cs
+++ b/AstarteDeviceSDKCSharp/Transport/MQTT/AstarteMqttV1Transport.cs
@@ -201,6 +201,32 @@ public override void RetryFailedMessages()
                 }
                 _failedMessageStorage.AckFirst();
             }
+
+            while (!_failedMessageStorage.IsCacheEmpty())
+            {
+                IAstarteFailedMessage? failedMessage = _failedMessageStorage.PeekFirstCache();
+                if (failedMessage is null)
+                {
+                    return;
+                }
+
+                if (failedMessage.IsExpired())
+                {
+                    // No need to send this anymore, drop it
+                    _failedMessageStorage.RejectFirstCache();
+                    continue;
+                }
+
+                try
+                {
+                    Task.Run(async () => await DoSendMessage(failedMessage));
+                }
+                catch (MqttCommunicationException e)
+                {
+                    throw new AstarteTransportException(e.Message);
+                }
+                _failedMessageStorage.AckFirstCache();
+            }
         }
 
         private async Task DoSendMessage(IAstarteFailedMessage failedMessage)