diff --git a/src/NzbDrone.Core/Download/Clients/Deluge/Deluge.cs b/src/NzbDrone.Core/Download/Clients/Deluge/Deluge.cs
index 568f69eca..c121a6a71 100644
--- a/src/NzbDrone.Core/Download/Clients/Deluge/Deluge.cs
+++ b/src/NzbDrone.Core/Download/Clients/Deluge/Deluge.cs
@@ -267,7 +267,11 @@ namespace NzbDrone.Core.Download.Clients.Deluge
             catch (Exception ex)
             {
                 _logger.Error(ex, "Failed to test connection");
-                return new NzbDroneValidationFailure(string.Empty, "Unknown exception: " + ex.Message);
+
+                return new NzbDroneValidationFailure("Host", "Unable to connect to Deluge")
+                       {
+                           DetailedDescription = ex.Message
+                       };
             }
 
             return null;
diff --git a/src/NzbDrone.Core/Download/Clients/Deluge/DelugeProxy.cs b/src/NzbDrone.Core/Download/Clients/Deluge/DelugeProxy.cs
index f7d151c71..21f10b164 100644
--- a/src/NzbDrone.Core/Download/Clients/Deluge/DelugeProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/Deluge/DelugeProxy.cs
@@ -266,6 +266,11 @@ namespace NzbDrone.Core.Download.Clients.Deluge
             }
             catch (WebException ex)
             {
+                if (ex.Status == WebExceptionStatus.TrustFailure)
+                {
+                    throw new DownloadClientUnavailableException("Unable to connect to Deluge, certificate validation failed.", ex);
+                }
+
                 throw new DownloadClientUnavailableException("Unable to connect to Deluge, please check your settings", ex);
             }
         }
diff --git a/src/NzbDrone.Core/Download/Clients/DownloadStation/Proxies/DiskStationProxyBase.cs b/src/NzbDrone.Core/Download/Clients/DownloadStation/Proxies/DiskStationProxyBase.cs
index 4e84666ed..75bf4a82f 100644
--- a/src/NzbDrone.Core/Download/Clients/DownloadStation/Proxies/DiskStationProxyBase.cs
+++ b/src/NzbDrone.Core/Download/Clients/DownloadStation/Proxies/DiskStationProxyBase.cs
@@ -85,6 +85,11 @@ namespace NzbDrone.Core.Download.Clients.DownloadStation.Proxies
             }
             catch (WebException ex)
             {
+                if (ex.Status == WebExceptionStatus.TrustFailure)
+                {
+                    throw new DownloadClientUnavailableException("Unable to connect to Diskstation, certificate validation failed.", ex);
+                }
+
                 throw new DownloadClientUnavailableException("Unable to connect to Diskstation, please check your settings", ex);
             }
 
diff --git a/src/NzbDrone.Core/Download/Clients/DownloadStation/TorrentDownloadStation.cs b/src/NzbDrone.Core/Download/Clients/DownloadStation/TorrentDownloadStation.cs
index 887474c9b..1980bfa8c 100644
--- a/src/NzbDrone.Core/Download/Clients/DownloadStation/TorrentDownloadStation.cs
+++ b/src/NzbDrone.Core/Download/Clients/DownloadStation/TorrentDownloadStation.cs
@@ -388,7 +388,11 @@ namespace NzbDrone.Core.Download.Clients.DownloadStation
             catch (Exception ex)
             {
                 _logger.Error(ex, "Error testing Torrent Download Station");
-                return new NzbDroneValidationFailure(string.Empty, $"Unknown exception: {ex.Message}");
+
+                return new NzbDroneValidationFailure("Host", "Unable to connect to Torrent Download Station")
+                       {
+                           DetailedDescription = ex.Message
+                       };
             }
         }
 
diff --git a/src/NzbDrone.Core/Download/Clients/DownloadStation/UsenetDownloadStation.cs b/src/NzbDrone.Core/Download/Clients/DownloadStation/UsenetDownloadStation.cs
index 62947b675..457e02019 100644
--- a/src/NzbDrone.Core/Download/Clients/DownloadStation/UsenetDownloadStation.cs
+++ b/src/NzbDrone.Core/Download/Clients/DownloadStation/UsenetDownloadStation.cs
@@ -286,7 +286,11 @@ namespace NzbDrone.Core.Download.Clients.DownloadStation
             catch (Exception ex)
             {
                 _logger.Error(ex, "Error testing Torrent Download Station");
-                return new NzbDroneValidationFailure(string.Empty, "Unknown exception: " + ex.Message);
+
+                return new NzbDroneValidationFailure("Host", "Unable to connect to Usenet Download Station")
+                       {
+                           DetailedDescription = ex.Message
+                       };
             }
         }
 
diff --git a/src/NzbDrone.Core/Download/Clients/Hadouken/Hadouken.cs b/src/NzbDrone.Core/Download/Clients/Hadouken/Hadouken.cs
index e46252bcb..43639bf34 100644
--- a/src/NzbDrone.Core/Download/Clients/Hadouken/Hadouken.cs
+++ b/src/NzbDrone.Core/Download/Clients/Hadouken/Hadouken.cs
@@ -158,7 +158,8 @@ namespace NzbDrone.Core.Download.Clients.Hadouken
 
                 if (version < new Version("5.1"))
                 {
-                    return new ValidationFailure(string.Empty, "Old Hadouken client with unsupported API, need 5.1 or higher");
+                    return new ValidationFailure(string.Empty,
+                        "Old Hadouken client with unsupported API, need 5.1 or higher");
                 }
             }
             catch (DownloadClientAuthenticationException ex)
@@ -167,6 +168,13 @@ namespace NzbDrone.Core.Download.Clients.Hadouken
 
                 return new NzbDroneValidationFailure("Password", "Authentication failed");
             }
+            catch (Exception ex)
+            {
+                return new NzbDroneValidationFailure("Host", "Unable to connect to Hadouken")
+                       {
+                           DetailedDescription = ex.Message
+                       };
+            }
 
             return null;
         }
diff --git a/src/NzbDrone.Core/Download/Clients/Hadouken/HadoukenProxy.cs b/src/NzbDrone.Core/Download/Clients/Hadouken/HadoukenProxy.cs
index fc9a57cd9..ec0dd1ffe 100644
--- a/src/NzbDrone.Core/Download/Clients/Hadouken/HadoukenProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/Hadouken/HadoukenProxy.cs
@@ -90,6 +90,11 @@ namespace NzbDrone.Core.Download.Clients.Hadouken
             }
             catch (WebException ex)
             {
+                if (ex.Status == WebExceptionStatus.TrustFailure)
+                {
+                    throw new DownloadClientUnavailableException("Unable to connect to Hadouken, certificate validation failed.", ex);
+                }
+
                 throw new DownloadClientUnavailableException("Unable to connect to Hadouken, please check your settings", ex);
             }
 
diff --git a/src/NzbDrone.Core/Download/Clients/NzbVortex/NzbVortex.cs b/src/NzbDrone.Core/Download/Clients/NzbVortex/NzbVortex.cs
index 9aec8af7f..ef67006ec 100644
--- a/src/NzbDrone.Core/Download/Clients/NzbVortex/NzbVortex.cs
+++ b/src/NzbDrone.Core/Download/Clients/NzbVortex/NzbVortex.cs
@@ -163,7 +163,11 @@ namespace NzbDrone.Core.Download.Clients.NzbVortex
             catch (Exception ex)
             {
                 _logger.Error(ex, "Unable to connect to NZBVortex");
-                return new ValidationFailure("Host", "Unable to connect to NZBVortex");
+
+                return new NzbDroneValidationFailure("Host", "Unable to connect to NZBVortex")
+                       {
+                           DetailedDescription = ex.Message
+                       };
             }
 
             return null;
diff --git a/src/NzbDrone.Core/Download/Clients/NzbVortex/NzbVortexProxy.cs b/src/NzbDrone.Core/Download/Clients/NzbVortex/NzbVortexProxy.cs
index a400b58d1..cf09d0c65 100644
--- a/src/NzbDrone.Core/Download/Clients/NzbVortex/NzbVortexProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/NzbVortex/NzbVortexProxy.cs
@@ -165,6 +165,11 @@ namespace NzbDrone.Core.Download.Clients.NzbVortex
             }
             catch (WebException ex)
             {
+                if (ex.Status == WebExceptionStatus.TrustFailure)
+                {
+                    throw new DownloadClientUnavailableException("Unable to connect to NZBVortex, certificate validation failed.", ex);
+                }
+
                 throw new DownloadClientUnavailableException("Unable to connect to NZBVortex, please check your settings", ex);
             }
         }
diff --git a/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrent.cs b/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrent.cs
index cb8a57c0d..fc1ce9b9f 100644
--- a/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrent.cs
+++ b/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrent.cs
@@ -376,7 +376,11 @@ namespace NzbDrone.Core.Download.Clients.QBittorrent
             catch (Exception ex)
             {
                 _logger.Error(ex, "Unable to test qBittorrent");
-                return new NzbDroneValidationFailure(string.Empty, "Unknown exception: " + ex.Message);
+
+                return new NzbDroneValidationFailure("Host", "Unable to connect to qBittorrent")
+                       {
+                           DetailedDescription = ex.Message
+                       };
             }
 
             return null;
diff --git a/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV2.cs b/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV2.cs
index 1c7e5d512..d292f5001 100644
--- a/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV2.cs
+++ b/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV2.cs
@@ -54,6 +54,11 @@ namespace NzbDrone.Core.Download.Clients.QBittorrent
             }
             catch (WebException ex)
             {
+                if (ex.Status == WebExceptionStatus.TrustFailure)
+                {
+                    throw new DownloadClientUnavailableException("Unable to connect to qBittorrent, certificate validation failed.", ex);
+                }
+
                 throw new DownloadClientException("Failed to connect to qBittorrent, check your settings.", ex);
             }
         }
diff --git a/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionBase.cs b/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionBase.cs
index 081c67f1e..f1a67a8c8 100644
--- a/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionBase.cs
+++ b/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionBase.cs
@@ -261,15 +261,17 @@ namespace NzbDrone.Core.Download.Clients.Transmission
             }
             catch (DownloadClientUnavailableException ex)
             {
-                _logger.Error(ex, "Unable to connect to transmission");
-                return new NzbDroneValidationFailure("Host", "Unable to connect")
-                {
-                    DetailedDescription = "Please verify the hostname and port."
-                };
+                _logger.Error(ex, ex.Message);
+
+                return new NzbDroneValidationFailure("Host", "Unable to connect to Transmission")
+                       {
+                           DetailedDescription = ex.Message
+                       };
             }
             catch (Exception ex)
             {
                 _logger.Error(ex, "Failed to test");
+
                 return new NzbDroneValidationFailure(string.Empty, "Unknown exception: " + ex.Message);
             }
         }
diff --git a/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionProxy.cs b/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionProxy.cs
index bf4c2cfdd..b9ae4605a 100644
--- a/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionProxy.cs
@@ -308,6 +308,11 @@ namespace NzbDrone.Core.Download.Clients.Transmission
             }
             catch (WebException ex)
             {
+                if (ex.Status == WebExceptionStatus.TrustFailure)
+                {
+                    throw new DownloadClientUnavailableException("Unable to connect to Transmission, certificate validation failed.", ex);
+                }
+
                 throw new DownloadClientUnavailableException("Unable to connect to Transmission, please check your settings", ex);
             }
         }
diff --git a/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrent.cs b/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrent.cs
index d3bcffb22..d3b1dc904 100644
--- a/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrent.cs
+++ b/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrent.cs
@@ -208,7 +208,11 @@ namespace NzbDrone.Core.Download.Clients.RTorrent
             catch (Exception ex)
             {
                 _logger.Error(ex, "Failed to test rTorrent");
-                return new NzbDroneValidationFailure(string.Empty, "Unknown exception: " + ex.Message);
+
+                return new NzbDroneValidationFailure("Host", "Unable to connect to rTorrent")
+                       {
+                           DetailedDescription = ex.Message
+                       };
             }
 
             return null;
diff --git a/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrentProxy.cs b/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrentProxy.cs
index aa8b40a8f..c3ddf5d9d 100644
--- a/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrentProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrentProxy.cs
@@ -265,6 +265,11 @@ namespace NzbDrone.Core.Download.Clients.RTorrent
             }
             catch (WebException ex)
             {
+                if (ex.Status == WebExceptionStatus.TrustFailure)
+                {
+                    throw new DownloadClientUnavailableException("Unable to connect to rTorrent, certificate validation failed.", ex);
+                }
+
                 throw new DownloadClientUnavailableException("Unable to connect to rTorrent, please check your settings", ex);
             }
         }
diff --git a/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrent.cs b/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrent.cs
index ecce4af45..4dad12922 100644
--- a/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrent.cs
+++ b/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrent.cs
@@ -291,7 +291,11 @@ namespace NzbDrone.Core.Download.Clients.UTorrent
             catch (Exception ex)
             {
                 _logger.Error(ex, "Failed to test uTorrent");
-                return new NzbDroneValidationFailure(string.Empty, "Unknown exception: " + ex.Message);
+
+                return new NzbDroneValidationFailure("Host", "Unable to connect to uTorrent")
+                       {
+                           DetailedDescription = ex.Message
+                       };
             }
 
             return null;
diff --git a/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrentProxy.cs b/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrentProxy.cs
index f954af748..fd5795cb2 100644
--- a/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrentProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrentProxy.cs
@@ -231,6 +231,11 @@ namespace NzbDrone.Core.Download.Clients.UTorrent
             }
             catch (WebException ex)
             {
+                if (ex.Status == WebExceptionStatus.TrustFailure)
+                {
+                    throw new DownloadClientUnavailableException("Unable to connect to uTorrent, certificate validation failed.", ex);
+                }
+
                 throw new DownloadClientException("Unable to connect to uTorrent, please check your settings", ex);
             }