diff --git a/src/Artemis.Core/Plugins/PluginFeature.cs b/src/Artemis.Core/Plugins/PluginFeature.cs
index ef3917ba0..149d42632 100644
--- a/src/Artemis.Core/Plugins/PluginFeature.cs
+++ b/src/Artemis.Core/Plugins/PluginFeature.cs
@@ -12,7 +12,7 @@ namespace Artemis.Core
     {
         private bool _isEnabled;
 
-        
+
         /// <summary>
         ///     Gets the plugin feature info related to this feature
         /// </summary>
@@ -37,6 +37,8 @@ namespace Artemis.Core
             internal set => SetAndNotify(ref _isEnabled, value);
         }
 
+        internal int AutoEnableAttempts { get; set; }
+
         /// <summary>
         ///     Gets the identifier of this plugin feature
         /// </summary>
@@ -137,6 +139,9 @@ namespace Artemis.Core
 
                 try
                 {
+                    if (isAutoEnable)
+                        AutoEnableAttempts++;
+
                     if (isAutoEnable && GetLockFileCreated())
                     {
                         // Don't wrap existing lock exceptions, simply rethrow them
@@ -157,6 +162,7 @@ namespace Artemis.Core
                         throw new ArtemisPluginException(Plugin, "Plugin load timeout");
 
                     Info.LoadException = null;
+                    AutoEnableAttempts = 0;
                     OnEnabled();
                 }
                 // If enable failed, put it back in a disabled state
diff --git a/src/Artemis.Core/Services/PluginManagementService.cs b/src/Artemis.Core/Services/PluginManagementService.cs
index de01c754f..5e4841829 100644
--- a/src/Artemis.Core/Services/PluginManagementService.cs
+++ b/src/Artemis.Core/Services/PluginManagementService.cs
@@ -5,6 +5,7 @@ using System.IO;
 using System.IO.Compression;
 using System.Linq;
 using System.Reflection;
+using System.Threading.Tasks;
 using Artemis.Core.DeviceProviders;
 using Artemis.Core.Ninject;
 using Artemis.Storage.Entities.General;
@@ -90,7 +91,7 @@ namespace Artemis.Core.Services
                 using StreamReader reader = new(metaDataFileEntry.Open());
                 PluginInfo builtInPluginInfo = CoreJson.DeserializeObject<PluginInfo>(reader.ReadToEnd())!;
                 string preferred = builtInPluginInfo.PreferredPluginDirectory;
-                
+
                 // Find the matching plugin in the plugin folder
                 DirectoryInfo? match = pluginDirectory.EnumerateDirectories().FirstOrDefault(d => d.Name == preferred);
                 if (match == null)
@@ -610,13 +611,38 @@ namespace Artemis.Core.Services
             }
             catch (Exception e)
             {
-                _logger.Warning(
-                    new ArtemisPluginException(pluginFeature.Plugin, $"Exception during SetEnabled(true) on {pluginFeature}", e),
-                    "Failed to enable plugin"
-                );
+                if (isAutoEnable)
+                {
+                    // Schedule a retry based on the amount of attempts
+                    if (pluginFeature.AutoEnableAttempts < 4)
+                    {
+                        TimeSpan retryDelay = TimeSpan.FromSeconds(pluginFeature.AutoEnableAttempts * 10);
+                        _logger.Warning(
+                            e,
+                            "Plugin feature '{feature} - {plugin}' failed to enable during attempt ({attempt}/3), scheduling a retry in {retryDelay}.",
+                            pluginFeature,
+                            pluginFeature.Plugin,
+                            pluginFeature.AutoEnableAttempts,
+                            retryDelay
+                        );
 
-                if (!isAutoEnable)
+                        Task.Run(async () =>
+                        {
+                            await Task.Delay(retryDelay);
+                            if (!pluginFeature.IsEnabled)
+                                EnablePluginFeature(pluginFeature, saveState, true);
+                        });
+                    }
+                    else
+                    {
+                        _logger.Warning(e, "Plugin feature '{feature} - {plugin}' failed to enable after 3 attempts, giving up.", pluginFeature, pluginFeature.Plugin);
+                    }
+                }
+                else
+                {
+                    _logger.Warning(e, "Plugin feature '{feature} - {plugin}' failed to enable.", pluginFeature, pluginFeature.Plugin);
                     throw;
+                }
             }
             finally
             {