diff --git a/src/NzbDrone.Common/Security/IgnoreCertErrorPolicy.cs b/src/NzbDrone.Common/Security/IgnoreCertErrorPolicy.cs
index 435ae0300..e46221e24 100644
--- a/src/NzbDrone.Common/Security/IgnoreCertErrorPolicy.cs
+++ b/src/NzbDrone.Common/Security/IgnoreCertErrorPolicy.cs
@@ -1,24 +1,45 @@
 using System.Net;
 using System.Net.Security;
 using System.Security.Cryptography.X509Certificates;
-using NzbDrone.Common.Extensions;
+using NLog;
+using NzbDrone.Common.EnvironmentInfo;
+using NzbDrone.Common.Instrumentation;
 
 namespace NzbDrone.Common.Security
 {
     public static class IgnoreCertErrorPolicy
     {
+        private static Logger _logger = NzbDroneLogger.GetLogger("IgnoreCertErrorPolicy");
+
         public static void Register()
         {
-            ServicePointManager.ServerCertificateValidationCallback = ValidationCallback;
+            ServicePointManager.ServerCertificateValidationCallback = ShouldByPassValidationError;
         }
 
-        private static bool ValidationCallback(object sender, X509Certificate certificate, X509Chain chain, SslPolicyErrors sslpolicyerrors)
+        private static bool ShouldByPassValidationError(object sender, X509Certificate certificate, X509Chain chain, SslPolicyErrors sslpolicyerrors)
         {
             var request = sender as HttpWebRequest;
 
-            if (request != null &&  sslpolicyerrors != SslPolicyErrors.None &&
-                (request.Address.OriginalString.ContainsIgnoreCase("nzbdrone.com") || request.Address.OriginalString.ContainsIgnoreCase("sonarr.tv"))
-               )
+            if (request == null)
+            {
+                return true;
+            }
+
+            if (sslpolicyerrors == SslPolicyErrors.None)
+            {
+                return true;
+            }
+
+            _logger.Warn("Request for {0} failed certificated validation. {1}", request.Address, sslpolicyerrors);
+
+            if (OsInfo.IsMono)
+            {
+                return true;
+            }
+
+            var host = request.Address.Host.ToLower();
+
+            if (host.EndsWith("nzbdrone.com") || host.EndsWith("sonarr.tv"))
             {
                 return false;
             }