diff --git a/src/Lidarr.Api.V1/Artist/ArtistController.cs b/src/Lidarr.Api.V1/Artist/ArtistController.cs
index 58f3fea59..f5a874f7d 100644
--- a/src/Lidarr.Api.V1/Artist/ArtistController.cs
+++ b/src/Lidarr.Api.V1/Artist/ArtistController.cs
@@ -53,6 +53,7 @@ namespace Lidarr.Api.V1.Artist
                             IMapCoversToLocal coverMapper,
                             IManageCommandQueue commandQueueManager,
                             IRootFolderService rootFolderService,
+                            RecycleBinValidator recycleBinValidator,
                             RootFolderValidator rootFolderValidator,
                             MappedNetworkDriveValidator mappedNetworkDriveValidator,
                             ArtistPathValidator artistPathValidator,
@@ -82,6 +83,7 @@ namespace Lidarr.Api.V1.Artist
                            .SetValidator(mappedNetworkDriveValidator)
                            .SetValidator(artistPathValidator)
                            .SetValidator(artistAncestorValidator)
+                           .SetValidator(recycleBinValidator)
                            .SetValidator(systemFolderValidator)
                            .When(s => !s.Path.IsNullOrWhiteSpace());
 
diff --git a/src/Lidarr.Api.V1/Config/MediaManagementConfigController.cs b/src/Lidarr.Api.V1/Config/MediaManagementConfigController.cs
index d2acc26a8..8a19c6175 100644
--- a/src/Lidarr.Api.V1/Config/MediaManagementConfigController.cs
+++ b/src/Lidarr.Api.V1/Config/MediaManagementConfigController.cs
@@ -10,12 +10,28 @@ namespace Lidarr.Api.V1.Config
     [V1ApiController("config/mediamanagement")]
     public class MediaManagementConfigController : ConfigController<MediaManagementConfigResource>
     {
-        public MediaManagementConfigController(IConfigService configService, PathExistsValidator pathExistsValidator, FolderChmodValidator folderChmodValidator)
+        public MediaManagementConfigController(IConfigService configService,
+                                           PathExistsValidator pathExistsValidator,
+                                           FolderChmodValidator folderChmodValidator,
+                                           FolderWritableValidator folderWritableValidator,
+                                           ArtistPathValidator artistPathValidator,
+                                           StartupFolderValidator startupFolderValidator,
+                                           SystemFolderValidator systemFolderValidator,
+                                           RootFolderAncestorValidator rootFolderAncestorValidator,
+                                           RootFolderValidator rootFolderValidator)
             : base(configService)
         {
+            SharedValidator.RuleFor(c => c.RecycleBin).IsValidPath()
+                                                      .SetValidator(folderWritableValidator)
+                                                      .SetValidator(rootFolderValidator)
+                                                      .SetValidator(pathExistsValidator)
+                                                      .SetValidator(artistPathValidator)
+                                                      .SetValidator(rootFolderAncestorValidator)
+                                                      .SetValidator(startupFolderValidator)
+                                                      .SetValidator(systemFolderValidator)
+                                                      .When(c => !string.IsNullOrWhiteSpace(c.RecycleBin));
             SharedValidator.RuleFor(c => c.RecycleBinCleanupDays).GreaterThanOrEqualTo(0);
             SharedValidator.RuleFor(c => c.ChmodFolder).SetValidator(folderChmodValidator).When(c => !string.IsNullOrEmpty(c.ChmodFolder) && (OsInfo.IsLinux || OsInfo.IsOsx));
-            SharedValidator.RuleFor(c => c.RecycleBin).IsValidPath().SetValidator(pathExistsValidator).When(c => !string.IsNullOrWhiteSpace(c.RecycleBin));
             SharedValidator.RuleFor(c => c.MinimumFreeSpaceWhenImporting).GreaterThanOrEqualTo(100);
         }
 
diff --git a/src/Lidarr.Api.V1/RootFolders/RootFolderController.cs b/src/Lidarr.Api.V1/RootFolders/RootFolderController.cs
index 48584f3bb..8d7473b4c 100644
--- a/src/Lidarr.Api.V1/RootFolders/RootFolderController.cs
+++ b/src/Lidarr.Api.V1/RootFolders/RootFolderController.cs
@@ -21,6 +21,7 @@ namespace Lidarr.Api.V1.RootFolders
                                 RootFolderValidator rootFolderValidator,
                                 PathExistsValidator pathExistsValidator,
                                 MappedNetworkDriveValidator mappedNetworkDriveValidator,
+                                RecycleBinValidator recycleBinValidator,
                                 StartupFolderValidator startupFolderValidator,
                                 SystemFolderValidator systemFolderValidator,
                                 FolderWritableValidator folderWritableValidator,
@@ -35,6 +36,7 @@ namespace Lidarr.Api.V1.RootFolders
                 .IsValidPath()
                 .SetValidator(mappedNetworkDriveValidator)
                 .SetValidator(startupFolderValidator)
+                .SetValidator(recycleBinValidator)
                 .SetValidator(pathExistsValidator)
                 .SetValidator(systemFolderValidator)
                 .SetValidator(folderWritableValidator);
diff --git a/src/NzbDrone.Core/Music/Utilities/AddArtistValidator.cs b/src/NzbDrone.Core/Music/Utilities/AddArtistValidator.cs
index c77cfacc2..77287c780 100644
--- a/src/NzbDrone.Core/Music/Utilities/AddArtistValidator.cs
+++ b/src/NzbDrone.Core/Music/Utilities/AddArtistValidator.cs
@@ -13,6 +13,7 @@ namespace NzbDrone.Core.Music
     public class AddArtistValidator : AbstractValidator<Artist>, IAddArtistValidator
     {
         public AddArtistValidator(RootFolderValidator rootFolderValidator,
+                                  RecycleBinValidator recycleBinValidator,
                                   ArtistPathValidator artistPathValidator,
                                   ArtistAncestorValidator artistAncestorValidator,
                                   QualityProfileExistsValidator qualityProfileExistsValidator,
@@ -21,6 +22,7 @@ namespace NzbDrone.Core.Music
             RuleFor(c => c.Path).Cascade(CascadeMode.StopOnFirstFailure)
                                 .IsValidPath()
                                 .SetValidator(rootFolderValidator)
+                                .SetValidator(recycleBinValidator)
                                 .SetValidator(artistPathValidator)
                                 .SetValidator(artistAncestorValidator);
 
diff --git a/src/NzbDrone.Core/Validation/Paths/ArtistPathValidator.cs b/src/NzbDrone.Core/Validation/Paths/ArtistPathValidator.cs
index 69f6c7c5d..824974e37 100644
--- a/src/NzbDrone.Core/Validation/Paths/ArtistPathValidator.cs
+++ b/src/NzbDrone.Core/Validation/Paths/ArtistPathValidator.cs
@@ -10,7 +10,7 @@ namespace NzbDrone.Core.Validation.Paths
         private readonly IArtistService _artistService;
 
         public ArtistPathValidator(IArtistService artistService)
-            : base("Path is already configured for another artist")
+            : base("Path is already configured for an existing artist")
         {
             _artistService = artistService;
         }
diff --git a/src/NzbDrone.Core/Validation/Paths/RecycleBinValidator.cs b/src/NzbDrone.Core/Validation/Paths/RecycleBinValidator.cs
new file mode 100644
index 000000000..a8a714fe6
--- /dev/null
+++ b/src/NzbDrone.Core/Validation/Paths/RecycleBinValidator.cs
@@ -0,0 +1,44 @@
+using FluentValidation.Validators;
+using NzbDrone.Common.Extensions;
+using NzbDrone.Core.Configuration;
+
+namespace NzbDrone.Core.Validation.Paths
+{
+    public class RecycleBinValidator : PropertyValidator
+    {
+        private readonly IConfigService _configService;
+
+        public RecycleBinValidator(IConfigService configService)
+            : base("Path is {relationship} configured recycle bin folder")
+        {
+            _configService = configService;
+        }
+
+        protected override bool IsValid(PropertyValidatorContext context)
+        {
+            var recycleBin = _configService.RecycleBin;
+            var folder = context.PropertyValue.ToString();
+
+            if (context.PropertyValue == null || recycleBin.IsNullOrWhiteSpace())
+            {
+                return true;
+            }
+
+            if (recycleBin.PathEquals(folder))
+            {
+                context.MessageFormatter.AppendArgument("relationship", "set to");
+
+                return false;
+            }
+
+            if (recycleBin.IsParentPath(folder))
+            {
+                context.MessageFormatter.AppendArgument("relationship", "child of");
+
+                return false;
+            }
+
+            return true;
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/Validation/Paths/RootFolderAncestorValidator.cs b/src/NzbDrone.Core/Validation/Paths/RootFolderAncestorValidator.cs
new file mode 100644
index 000000000..19f0800b5
--- /dev/null
+++ b/src/NzbDrone.Core/Validation/Paths/RootFolderAncestorValidator.cs
@@ -0,0 +1,28 @@
+using System.Linq;
+using FluentValidation.Validators;
+using NzbDrone.Common.Extensions;
+using NzbDrone.Core.RootFolders;
+
+namespace NzbDrone.Core.Validation.Paths
+{
+    public class RootFolderAncestorValidator : PropertyValidator
+    {
+        private readonly IRootFolderService _rootFolderService;
+
+        public RootFolderAncestorValidator(IRootFolderService rootFolderService)
+            : base("Path is an ancestor of an existing root folder")
+        {
+            _rootFolderService = rootFolderService;
+        }
+
+        protected override bool IsValid(PropertyValidatorContext context)
+        {
+            if (context.PropertyValue == null)
+            {
+                return true;
+            }
+
+            return !_rootFolderService.All().Any(s => context.PropertyValue.ToString().IsParentPath(s.Path));
+        }
+    }
+}