diff --git a/src/NzbDrone.Core/HealthCheck/Checks/RecyclingBinCheck.cs b/src/NzbDrone.Core/HealthCheck/Checks/RecyclingBinCheck.cs
new file mode 100644
index 000000000..8a83faac2
--- /dev/null
+++ b/src/NzbDrone.Core/HealthCheck/Checks/RecyclingBinCheck.cs
@@ -0,0 +1,38 @@
+using NzbDrone.Common.Disk;
+using NzbDrone.Common.Extensions;
+using NzbDrone.Core.Configuration;
+using NzbDrone.Core.MediaFiles.Events;
+
+namespace NzbDrone.Core.HealthCheck.Checks
+{
+    [CheckOn(typeof(EpisodeImportedEvent), CheckOnCondition.FailedOnly)]
+    [CheckOn(typeof(EpisodeImportFailedEvent), CheckOnCondition.SuccessfulOnly)]
+    public class RecyclingBinCheck : HealthCheckBase
+    {
+        private readonly IConfigService _configService;
+        private readonly IDiskProvider _diskProvider;
+
+        public RecyclingBinCheck(IConfigService configService, IDiskProvider diskProvider)
+        {
+            _configService = configService;
+            _diskProvider = diskProvider;
+        }
+
+        public override HealthCheck Check()
+        {
+            var recycleBin = _configService.RecycleBin;
+
+            if (recycleBin.IsNullOrWhiteSpace())
+            {
+                return new HealthCheck(GetType());
+            }
+
+            if (!_diskProvider.FolderWritable(recycleBin))
+            {
+                return new HealthCheck(GetType(), HealthCheckResult.Error, $"Unable to write to configured recycling bin folder: {recycleBin}. Ensure this path exists and is writable by the user running Sonarr");
+            }
+
+            return new HealthCheck(GetType());
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/HealthCheck/HealthCheckService.cs b/src/NzbDrone.Core/HealthCheck/HealthCheckService.cs
index ac734fcce..c24616c71 100644
--- a/src/NzbDrone.Core/HealthCheck/HealthCheckService.cs
+++ b/src/NzbDrone.Core/HealthCheck/HealthCheckService.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.Collections.Generic;
 using System.Linq;
 using NLog;
diff --git a/src/NzbDrone.Core/MediaFiles/EpisodeImport/ImportApprovedEpisodes.cs b/src/NzbDrone.Core/MediaFiles/EpisodeImport/ImportApprovedEpisodes.cs
index 096ccd0cf..a5feeaf4a 100644
--- a/src/NzbDrone.Core/MediaFiles/EpisodeImport/ImportApprovedEpisodes.cs
+++ b/src/NzbDrone.Core/MediaFiles/EpisodeImport/ImportApprovedEpisodes.cs
@@ -151,6 +151,13 @@ namespace NzbDrone.Core.MediaFiles.EpisodeImport
 
                     _commandQueueManager.Push(new RescanSeriesCommand(localEpisode.Series.Id));
                 }
+                catch (RecycleBinException e)
+                {
+                    _logger.Warn(e, "Couldn't import episode " + localEpisode);
+                    _eventAggregator.PublishEvent(new EpisodeImportFailedEvent(e, localEpisode, newDownload, downloadClientItem));
+
+                    importResults.Add(new ImportResult(importDecision, "Failed to import episode, unable to move existing file to the Recycle Bin."));
+                }
                 catch (Exception e)
                 {
                     _logger.Warn(e, "Couldn't import episode " + localEpisode);
diff --git a/src/NzbDrone.Core/MediaFiles/EpisodeImport/RecycleBinException.cs b/src/NzbDrone.Core/MediaFiles/EpisodeImport/RecycleBinException.cs
new file mode 100644
index 000000000..645951518
--- /dev/null
+++ b/src/NzbDrone.Core/MediaFiles/EpisodeImport/RecycleBinException.cs
@@ -0,0 +1,28 @@
+using System;
+using System.IO;
+using System.Runtime.Serialization;
+
+namespace NzbDrone.Core.MediaFiles.EpisodeImport
+{
+    public class RecycleBinException : DirectoryNotFoundException
+    {
+        public RecycleBinException()
+        {
+        }
+
+        public RecycleBinException(string message)
+            : base(message)
+        {
+        }
+
+        public RecycleBinException(string message, Exception innerException)
+            : base(message, innerException)
+        {
+        }
+
+        protected RecycleBinException(SerializationInfo info, StreamingContext context)
+            : base(info, context)
+        {
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/MediaFiles/RecycleBinProvider.cs b/src/NzbDrone.Core/MediaFiles/RecycleBinProvider.cs
index 70060021a..fd35deb9d 100644
--- a/src/NzbDrone.Core/MediaFiles/RecycleBinProvider.cs
+++ b/src/NzbDrone.Core/MediaFiles/RecycleBinProvider.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.IO;
 using NLog;
 using NzbDrone.Common.Disk;
@@ -6,6 +6,7 @@ using NzbDrone.Common.EnvironmentInfo;
 using NzbDrone.Common.Extensions;
 using NzbDrone.Core.Configuration;
 using NzbDrone.Core.MediaFiles.Commands;
+using NzbDrone.Core.MediaFiles.EpisodeImport;
 using NzbDrone.Core.Messaging.Commands;
 using NzbDrone.Core.Messaging.Events;
 using NzbDrone.Core.Tv.Events;
@@ -98,7 +99,7 @@ namespace NzbDrone.Core.MediaFiles
                 catch (IOException e)
                 {
                     _logger.Error(e, "Unable to create the folder '{0}' in the recycling bin for the file '{1}'", destinationFolder, fileInfo.Name);
-                    throw;
+                    throw new RecycleBinException($"Unable to create the folder '{destinationFolder}' in the recycling bin for the file '{fileInfo.Name}'", e);
                 }
 
                 var index = 1;
@@ -123,7 +124,7 @@ namespace NzbDrone.Core.MediaFiles
                 catch (IOException e)
                 {
                     _logger.Error(e, "Unable to move '{0}' to the recycling bin: '{1}'", path, destination);
-                    throw;
+                    throw new RecycleBinException($"Unable to move '{path}' to the recycling bin: '{destination}'", e);
                 }
 
                 SetLastWriteTime(destination, DateTime.UtcNow);