diff --git a/src/NzbDrone.Common/Disk/LongPathSupport.cs b/src/NzbDrone.Common/Disk/LongPathSupport.cs
new file mode 100644
index 000000000..916123f8d
--- /dev/null
+++ b/src/NzbDrone.Common/Disk/LongPathSupport.cs
@@ -0,0 +1,15 @@
+using System;
+
+namespace NzbDrone.Common.Disk
+{
+    public static class LongPathSupport
+    {
+        public static void Enable()
+        {
+            // Mono has an issue with enabling long path support via app.config.
+            // This works for both mono and .net on Windows.
+            AppContext.SetSwitch("Switch.System.IO.UseLegacyPathHandling", false);
+            AppContext.SetSwitch("Switch.System.IO.BlockLongPaths", false);
+        }
+    }
+}
diff --git a/src/NzbDrone.Common/NzbDrone.Common.csproj b/src/NzbDrone.Common/NzbDrone.Common.csproj
index 21388fb7f..7942d2188 100644
--- a/src/NzbDrone.Common/NzbDrone.Common.csproj
+++ b/src/NzbDrone.Common/NzbDrone.Common.csproj
@@ -106,6 +106,7 @@
     <Compile Include="Disk\FileSystemLookupService.cs" />
     <Compile Include="Disk\DriveInfoMount.cs" />
     <Compile Include="Disk\IMount.cs" />
+    <Compile Include="Disk\LongPathSupport.cs" />
     <Compile Include="Disk\MountOptions.cs" />
     <Compile Include="Disk\RelativeFileSystemModel.cs" />
     <Compile Include="Disk\FileSystemModel.cs" />
diff --git a/src/NzbDrone.Host/Bootstrap.cs b/src/NzbDrone.Host/Bootstrap.cs
index 28a9be29b..a562f44e8 100644
--- a/src/NzbDrone.Host/Bootstrap.cs
+++ b/src/NzbDrone.Host/Bootstrap.cs
@@ -3,6 +3,7 @@ using System.Reflection;
 using System.Threading;
 using NLog;
 using NzbDrone.Common.Composition;
+using NzbDrone.Common.Disk;
 using NzbDrone.Common.EnvironmentInfo;
 using NzbDrone.Common.Exceptions;
 using NzbDrone.Common.Instrumentation;
@@ -32,6 +33,8 @@ namespace NzbDrone.Host
                     throw new TerminateApplicationException("Missing system requirements");
                 }
 
+                LongPathSupport.Enable();
+
                 _container = MainAppContainerBuilder.BuildContainer(startupContext);
                 _container.Resolve<IAppFolderFactory>().Register();
                 _container.Resolve<IProvidePidFile>().Write();
diff --git a/src/NzbDrone.Host/app.config b/src/NzbDrone.Host/app.config
index cdde64137..dfc9fa3f9 100644
--- a/src/NzbDrone.Host/app.config
+++ b/src/NzbDrone.Host/app.config
@@ -10,7 +10,6 @@
   </startup>
   <runtime>
     <loadFromRemoteSources enabled="true" />
-    <AppContextSwitchOverrides value="Switch.System.IO.UseLegacyPathHandling=false;Switch.System.IO.BlockLongPaths=false" />
     <assemblyBinding xmlns="urn:schemas-microsoft-com:asm.v1">
       <probing privatePath="libs" />
       <dependentAssembly>