diff --git a/src/NzbDrone.Core/HealthCheck/Checks/RecyclingBinCheck.cs b/src/NzbDrone.Core/HealthCheck/Checks/RecyclingBinCheck.cs
new file mode 100644
index 000000000..02f48855a
--- /dev/null
+++ b/src/NzbDrone.Core/HealthCheck/Checks/RecyclingBinCheck.cs
@@ -0,0 +1,41 @@
+using NzbDrone.Common.Disk;
+using NzbDrone.Common.Extensions;
+using NzbDrone.Core.Configuration;
+using NzbDrone.Core.Localization;
+using NzbDrone.Core.MediaFiles.Events;
+
+namespace NzbDrone.Core.HealthCheck.Checks
+{
+    [CheckOn(typeof(TrackImportedEvent), CheckOnCondition.FailedOnly)]
+    [CheckOn(typeof(TrackImportFailedEvent), CheckOnCondition.SuccessfulOnly)]
+    public class RecyclingBinCheck : HealthCheckBase
+    {
+        private readonly IConfigService _configService;
+        private readonly IDiskProvider _diskProvider;
+        private readonly ILocalizationService _localizationService;
+
+        public RecyclingBinCheck(IConfigService configService, IDiskProvider diskProvider, ILocalizationService localizationService)
+        {
+            _configService = configService;
+            _diskProvider = diskProvider;
+            _localizationService = localizationService;
+        }
+
+        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, string.Format(_localizationService.GetLocalizedString("RecycleBinUnableToWriteHealthCheck"), recycleBin), "#cannot-write-recycle-bin");
+            }
+
+            return new HealthCheck(GetType());
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/Localization/Core/en.json b/src/NzbDrone.Core/Localization/Core/en.json
index 9cc512733..484113ed4 100644
--- a/src/NzbDrone.Core/Localization/Core/en.json
+++ b/src/NzbDrone.Core/Localization/Core/en.json
@@ -623,6 +623,7 @@
   "RecycleBinCleanupDaysHelpText": "Set to 0 to disable automatic cleanup",
   "RecycleBinCleanupDaysHelpTextWarning": "Files in the recycle bin older than the selected number of days will be cleaned up automatically",
   "RecycleBinHelpText": "Track files will go here when deleted instead of being permanently deleted",
+  "RecycleBinUnableToWriteHealthCheck": "Unable to write to configured recycling bin folder: {0}. Ensure this path exists and is writable by the user running Lidarr",
   "RecyclingBin": "Recycling Bin",
   "RecyclingBinCleanup": "Recycling Bin Cleanup",
   "Redownload": "Redownload",
@@ -926,4 +927,4 @@
   "WriteMetadataToAudioFiles": "Write Metadata to Audio Files",
   "Year": "Year",
   "YesCancel": "Yes, Cancel"
-}
\ No newline at end of file
+}
diff --git a/src/NzbDrone.Core/MediaFiles/RecycleBinProvider.cs b/src/NzbDrone.Core/MediaFiles/RecycleBinProvider.cs
index 2c3a29cf6..9e8b4320d 100644
--- a/src/NzbDrone.Core/MediaFiles/RecycleBinProvider.cs
+++ b/src/NzbDrone.Core/MediaFiles/RecycleBinProvider.cs
@@ -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.TrackImport;
 using NzbDrone.Core.Messaging.Commands;
 
 namespace NzbDrone.Core.MediaFiles
@@ -96,7 +97,7 @@ 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;
@@ -121,7 +122,7 @@ 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);
diff --git a/src/NzbDrone.Core/MediaFiles/TrackImport/ImportApprovedTracks.cs b/src/NzbDrone.Core/MediaFiles/TrackImport/ImportApprovedTracks.cs
index db9627ef3..7988edda8 100644
--- a/src/NzbDrone.Core/MediaFiles/TrackImport/ImportApprovedTracks.cs
+++ b/src/NzbDrone.Core/MediaFiles/TrackImport/ImportApprovedTracks.cs
@@ -266,6 +266,13 @@ namespace NzbDrone.Core.MediaFiles.TrackImport
 
                     importResults.Add(new ImportResult(importDecision, "Failed to import track, Permissions error"));
                 }
+                catch (RecycleBinException e)
+                {
+                    _logger.Warn(e, "Couldn't import track " + localTrack);
+                    _eventAggregator.PublishEvent(new TrackImportFailedEvent(e, localTrack, !localTrack.ExistingFile, downloadClientItem));
+
+                    importResults.Add(new ImportResult(importDecision, "Failed to import track, unable to move existing file to the Recycle Bin."));
+                }
                 catch (Exception e)
                 {
                     _logger.Warn(e, "Couldn't import track " + localTrack);
diff --git a/src/NzbDrone.Core/MediaFiles/TrackImport/RecycleBinException.cs b/src/NzbDrone.Core/MediaFiles/TrackImport/RecycleBinException.cs
new file mode 100644
index 000000000..765ebeb25
--- /dev/null
+++ b/src/NzbDrone.Core/MediaFiles/TrackImport/RecycleBinException.cs
@@ -0,0 +1,28 @@
+using System;
+using System.IO;
+using System.Runtime.Serialization;
+
+namespace NzbDrone.Core.MediaFiles.TrackImport
+{
+    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)
+        {
+        }
+    }
+}