From fc4170d9dc57786897ee5ef08758251a72d5d066 Mon Sep 17 00:00:00 2001
From: Mark McDowall <mark@mcdowall.ca>
Date: Mon, 6 Dec 2021 20:15:35 -0800
Subject: [PATCH] Fixed: Report certificate validation failures when
 configuring Plex Media Server connection

Closes #2520

(cherry picked from commit ec62884649f7af5f0a29346741754590e6de99ce)
---
 .../Notifications/Plex/Server/PlexServerProxy.cs  |  7 ++++++-
 .../Plex/Server/PlexServerService.cs              | 15 ++++++++++++---
 2 files changed, 18 insertions(+), 4 deletions(-)

diff --git a/src/NzbDrone.Core/Notifications/Plex/Server/PlexServerProxy.cs b/src/NzbDrone.Core/Notifications/Plex/Server/PlexServerProxy.cs
index eaa5cf968..46fe945a5 100644
--- a/src/NzbDrone.Core/Notifications/Plex/Server/PlexServerProxy.cs
+++ b/src/NzbDrone.Core/Notifications/Plex/Server/PlexServerProxy.cs
@@ -195,7 +195,12 @@ namespace NzbDrone.Core.Notifications.Plex.Server
             }
             catch (WebException ex)
             {
-                throw new PlexException("Unable to connect to Plex Media Server", ex);
+                if (ex.Status == WebExceptionStatus.TrustFailure)
+                {
+                    throw new PlexException("Unable to connect to Plex Media Server, certificate validation failed.", ex);
+                }
+
+                throw new PlexException($"Unable to connect to Plex Media Server, {ex.Message}", ex);
             }
 
             return response.Content;
diff --git a/src/NzbDrone.Core/Notifications/Plex/Server/PlexServerService.cs b/src/NzbDrone.Core/Notifications/Plex/Server/PlexServerService.cs
index 0a530d15f..989c60e9b 100644
--- a/src/NzbDrone.Core/Notifications/Plex/Server/PlexServerService.cs
+++ b/src/NzbDrone.Core/Notifications/Plex/Server/PlexServerService.cs
@@ -8,6 +8,7 @@ using NLog;
 using NzbDrone.Common.Cache;
 using NzbDrone.Common.Extensions;
 using NzbDrone.Core.Music;
+using NzbDrone.Core.Validation;
 
 namespace NzbDrone.Core.Notifications.Plex.Server
 {
@@ -192,13 +193,21 @@ namespace NzbDrone.Core.Notifications.Plex.Server
             }
             catch (PlexAuthenticationException ex)
             {
-                _logger.Error(ex, "Unable to connect to Plex Server");
+                _logger.Error(ex, "Unable to connect to Plex Media Server");
                 return new ValidationFailure("AuthToken", "Invalid authentication token");
             }
+            catch (PlexException ex)
+            {
+                return new NzbDroneValidationFailure("Host", ex.Message);
+            }
             catch (Exception ex)
             {
-                _logger.Error(ex, "Unable to connect to Plex Server");
-                return new ValidationFailure("Host", "Unable to connect to Plex Server");
+                _logger.Error(ex, "Unable to connect to Plex Media Server");
+
+                return new NzbDroneValidationFailure("Host", "Unable to connect to Plex Media Server")
+                       {
+                           DetailedDescription = ex.Message
+                       };
             }
 
             return null;