diff --git a/src/NzbDrone.Core/Download/Clients/Deluge/Deluge.cs b/src/NzbDrone.Core/Download/Clients/Deluge/Deluge.cs
index 5907680a2..91d421529 100644
--- a/src/NzbDrone.Core/Download/Clients/Deluge/Deluge.cs
+++ b/src/NzbDrone.Core/Download/Clients/Deluge/Deluge.cs
@@ -260,7 +260,11 @@ 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 c34352fe6..abd6c8ba7 100644
--- a/src/NzbDrone.Core/Download/Clients/Deluge/DelugeProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/Deluge/DelugeProxy.cs
@@ -263,6 +263,11 @@ 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 a88b03549..3c48d31d8 100644
--- a/src/NzbDrone.Core/Download/Clients/DownloadStation/Proxies/DiskStationProxyBase.cs
+++ b/src/NzbDrone.Core/Download/Clients/DownloadStation/Proxies/DiskStationProxyBase.cs
@@ -84,6 +84,11 @@ 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 5840288bc..07ff72c42 100644
--- a/src/NzbDrone.Core/Download/Clients/DownloadStation/TorrentDownloadStation.cs
+++ b/src/NzbDrone.Core/Download/Clients/DownloadStation/TorrentDownloadStation.cs
@@ -379,7 +379,11 @@ 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 14ebc67a4..ea2b4d8b8 100644
--- a/src/NzbDrone.Core/Download/Clients/DownloadStation/UsenetDownloadStation.cs
+++ b/src/NzbDrone.Core/Download/Clients/DownloadStation/UsenetDownloadStation.cs
@@ -278,7 +278,11 @@ 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 1fb789fc9..fa5ee215c 100644
--- a/src/NzbDrone.Core/Download/Clients/Hadouken/Hadouken.cs
+++ b/src/NzbDrone.Core/Download/Clients/Hadouken/Hadouken.cs
@@ -155,7 +155,8 @@ 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)
@@ -164,6 +165,13 @@ 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 faeddd5ee..b51479d10 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 7faeae119..769dc0e82 100644
--- a/src/NzbDrone.Core/Download/Clients/NzbVortex/NzbVortex.cs
+++ b/src/NzbDrone.Core/Download/Clients/NzbVortex/NzbVortex.cs
@@ -160,7 +160,11 @@ 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 c5e8ef4c7..299fa7f9d 100644
--- a/src/NzbDrone.Core/Download/Clients/NzbVortex/NzbVortexProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/NzbVortex/NzbVortexProxy.cs
@@ -166,6 +166,11 @@ 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 18ad75777..be9d26225 100644
--- a/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrent.cs
+++ b/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrent.cs
@@ -307,7 +307,11 @@ 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 b6cb3bc49..cc046475d 100644
--- a/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV2.cs
+++ b/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV2.cs
@@ -55,6 +55,11 @@ 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 d375c6503..945276457 100644
--- a/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionBase.cs
+++ b/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionBase.cs
@@ -247,14 +247,15 @@ namespace NzbDrone.Core.Download.Clients.Transmission
             {
                 _logger.Error(ex, ex.Message);
 
-                return new NzbDroneValidationFailure("Host", "Unable to connect")
-                {
-                    DetailedDescription = "Please verify the hostname and port."
-                };
+                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 393ecf914..2d3aaa03a 100644
--- a/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionProxy.cs
@@ -305,6 +305,11 @@ 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 d77f9d705..ddd41f435 100644
--- a/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrent.cs
+++ b/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrent.cs
@@ -200,7 +200,11 @@ 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 b35063076..00b03ebf5 100644
--- a/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrentProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrentProxy.cs
@@ -266,6 +266,11 @@ 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 13f6cc6fd..429cec5dd 100644
--- a/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrent.cs
+++ b/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrent.cs
@@ -286,7 +286,11 @@ 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 f8a76892b..84f64b8cc 100644
--- a/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrentProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrentProxy.cs
@@ -228,6 +228,11 @@ 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);
             }