diff --git a/Shokofin/Configuration/PluginConfiguration.cs b/Shokofin/Configuration/PluginConfiguration.cs
index 7358a7d0..f0c05343 100644
--- a/Shokofin/Configuration/PluginConfiguration.cs
+++ b/Shokofin/Configuration/PluginConfiguration.cs
@@ -16,6 +16,13 @@ public class PluginConfiguration : BasePluginConfiguration
 {
     #region Connection
 
+    /// <summary>
+    /// Helper for the web ui to show the windows only warning, and to disable
+    /// the VFS by default if we cannot create symbolic links.
+    /// </summary>
+    [XmlIgnore, JsonInclude]
+    public bool CanCreateSymbolicLinks => Plugin.Instance.CanCreateSymbolicLinks;
+
     /// <summary>
     /// The URL for where to connect to shoko internally.
     /// And externally if no <seealso cref="PublicUrl"/> is set.
@@ -293,7 +300,7 @@ public PluginConfiguration()
         TitleAllowAny = false;
         DescriptionSourceList = new[] { TextSourceType.AniDb, TextSourceType.TvDb, TextSourceType.TMDB };
         DescriptionSourceOrder = new[] { TextSourceType.AniDb, TextSourceType.TvDb, TextSourceType.TMDB };
-        VirtualFileSystem = true;
+        VirtualFileSystem = CanCreateSymbolicLinks;
         VirtualFileSystemThreads = 10;
         UseGroupsForShows = false;
         SeparateMovies = false;
diff --git a/Shokofin/Configuration/configController.js b/Shokofin/Configuration/configController.js
index df841d99..92cf6a9d 100644
--- a/Shokofin/Configuration/configController.js
+++ b/Shokofin/Configuration/configController.js
@@ -639,6 +639,10 @@ export default function (page) {
         else {
             form.querySelector("#ServerVersion").value = "Version N/A";
         }
+        if (!config.CanCreateSymbolicLinks) {
+            form.querySelector("#WindowsSymLinkWarning1").removeAttribute("hidden");
+            form.querySelector("#WindowsSymLinkWarning2").removeAttribute("hidden");
+        }
         if (config.ApiKey) {
             form.querySelector("#Url").setAttribute("disabled", "");
             form.querySelector("#Username").setAttribute("disabled", "");
diff --git a/Shokofin/Configuration/configPage.html b/Shokofin/Configuration/configPage.html
index c2eca30f..2f64d89b 100644
--- a/Shokofin/Configuration/configPage.html
+++ b/Shokofin/Configuration/configPage.html
@@ -228,6 +228,7 @@ <h3>Media Folder Settings</h3>
                                 </label>
                                 <div class="fieldDescription checkboxFieldDescription">
                                     <div>Enables the use of the Virtual File System&trade; for any new media libraries managed by the plugin.</div>
+                                    <div id="WindowsSymLinkWarning1" hidden><strong>Warning</strong>: Windows users are required to <a href="https://learn.microsoft.com/en-us/windows/apps/get-started/developer-mode-features-and-debugging#use-regedit-to-enable-your-device" target="_blank" rel="noopener noreferrer">enable Developer Mode</a> to be able to create symbolic links, a feature <strong>required</strong> to use the VFS.</div>
                                     <details style="margin-top: 0.5em">
                                         <summary style="margin-bottom: 0.25em">What does this mean?</summary>
                                         Enabling this setting should in theory make it so you won't have to think about file structure incompatibilities, since it will override your existing file structure and replace it with a layer of symbolic links managed by the plugin instead of your actual file structure.
@@ -272,6 +273,7 @@ <h3>Media Folder Settings</h3>
                                 </label>
                                 <div class="fieldDescription checkboxFieldDescription">
                                     <div>Enables the use of the Virtual File System&trade; for the library.</div>
+                                    <div id="WindowsSymLinkWarning2" hidden><strong>Warning</strong>: Windows users are required to <a href="https://learn.microsoft.com/en-us/windows/apps/get-started/developer-mode-features-and-debugging#use-regedit-to-enable-your-device" target="_blank" rel="noopener noreferrer">enable Developer Mode</a> to be able to create symbolic links, a feature <strong>required</strong> to use the VFS.</div>
                                     <details style="margin-top: 0.5em">
                                         <summary style="margin-bottom: 0.25em">What does this mean?</summary>
                                         Enabling this setting should in theory make it so you won't have to think about file structure incompatibilities, since it will override your existing file structure and replace it with a layer of symbolic links managed by the plugin instead of your actual file structure.
diff --git a/Shokofin/Plugin.cs b/Shokofin/Plugin.cs
index 4f9cfe1f..472b0cf1 100644
--- a/Shokofin/Plugin.cs
+++ b/Shokofin/Plugin.cs
@@ -2,6 +2,7 @@
 using System.Collections.Generic;
 using System.IO;
 using System.Linq;
+using System.Runtime.InteropServices;
 using MediaBrowser.Common.Configuration;
 using MediaBrowser.Common.Plugins;
 using MediaBrowser.Model.Plugins;
@@ -19,6 +20,8 @@ public class Plugin : BasePlugin<PluginConfiguration>, IHasWebPages
 
     public override Guid Id => Guid.Parse("5216ccbf-d24a-4eb3-8a7e-7da4230b7052");
 
+    public readonly bool CanCreateSymbolicLinks;
+
     private readonly ILogger<Plugin> Logger;
 
     /// <summary>
@@ -33,7 +36,28 @@ public Plugin(IApplicationPaths applicationPaths, IXmlSerializer xmlSerializer,
         IgnoredFolders = Configuration.IgnoredFolders.ToHashSet();
         VirtualRoot = Path.Combine(applicationPaths.ProgramDataPath, "Shokofin", "VFS");
         Logger = logger;
-        Logger.LogInformation("Virtual File System Location; {Path}", VirtualRoot);
+        CanCreateSymbolicLinks = true;
+        if (RuntimeInformation.IsOSPlatform(OSPlatform.Windows)) {
+            var target = Path.Combine(Path.GetDirectoryName(VirtualRoot)!, "TestTarget.txt");
+            var link = Path.Combine(Path.GetDirectoryName(VirtualRoot)!, "TestLink.txt");
+            try {
+                if (!Directory.Exists(Path.GetDirectoryName(VirtualRoot)!))
+                    Directory.CreateDirectory(Path.GetDirectoryName(VirtualRoot)!);
+                File.Create(target);
+                File.CreateSymbolicLink(link, target);
+            }
+            catch {
+                CanCreateSymbolicLinks = false;
+            }
+            finally {
+                if (File.Exists(link))
+                    File.Delete(link);
+                if (File.Exists(target))
+                    File.Delete(target);
+            }
+        }
+        Logger.LogDebug("Virtual File System Location; {Path}", VirtualRoot);
+        Logger.LogDebug("Can create symbolic links; {Value}", CanCreateSymbolicLinks);
     }
 
     public void OnConfigChanged(object? sender, BasePluginConfiguration e)