diff --git a/Emby.Server.Implementations/ApplicationHost.cs b/Emby.Server.Implementations/ApplicationHost.cs
index 7b3d07dfc1..7b40f530c9 100644
--- a/Emby.Server.Implementations/ApplicationHost.cs
+++ b/Emby.Server.Implementations/ApplicationHost.cs
@@ -193,11 +193,6 @@ namespace Emby.Server.Implementations
         /// </summary>
         private string PublishedServerUrl => _startupConfig[AddressOverrideKey];
 
-        /// <summary>
-        /// Gets a value indicating whether this instance can self restart.
-        /// </summary>
-        public bool CanSelfRestart => _startupOptions.RestartPath is not null;
-
         public bool CoreStartupHasCompleted { get; private set; }
 
         public virtual bool CanLaunchWebBrowser
@@ -935,17 +930,13 @@ namespace Emby.Server.Implementations
         /// </summary>
         public void Restart()
         {
-            if (!CanSelfRestart)
-            {
-                throw new PlatformNotSupportedException("The server is unable to self-restart. Please restart manually.");
-            }
-
             if (IsShuttingDown)
             {
                 return;
             }
 
             IsShuttingDown = true;
+            _pluginManager.UnloadAssemblies();
 
             Task.Run(async () =>
             {
@@ -1047,7 +1038,7 @@ namespace Emby.Server.Implementations
                 CachePath = ApplicationPaths.CachePath,
                 OperatingSystem = MediaBrowser.Common.System.OperatingSystem.Id.ToString(),
                 OperatingSystemDisplayName = MediaBrowser.Common.System.OperatingSystem.Name,
-                CanSelfRestart = CanSelfRestart,
+                CanSelfRestart = true,
                 CanLaunchWebBrowser = CanLaunchWebBrowser,
                 TranscodingTempPath = ConfigurationManager.GetTranscodePath(),
                 ServerName = FriendlyName,
diff --git a/Emby.Server.Implementations/IStartupOptions.cs b/Emby.Server.Implementations/IStartupOptions.cs
index 3769ae4dd8..b7bcaace1b 100644
--- a/Emby.Server.Implementations/IStartupOptions.cs
+++ b/Emby.Server.Implementations/IStartupOptions.cs
@@ -20,16 +20,6 @@ namespace Emby.Server.Implementations
         /// </summary>
         string? PackageName { get; }
 
-        /// <summary>
-        /// Gets the value of the --restartpath command line option.
-        /// </summary>
-        string? RestartPath { get; }
-
-        /// <summary>
-        /// Gets the value of the --restartargs command line option.
-        /// </summary>
-        string? RestartArgs { get; }
-
         /// <summary>
         /// Gets the value of the --published-server-url command line option.
         /// </summary>
diff --git a/Emby.Server.Implementations/Plugins/PluginManager.cs b/Emby.Server.Implementations/Plugins/PluginManager.cs
index 14e7c22696..6ef66f2b5d 100644
--- a/Emby.Server.Implementations/Plugins/PluginManager.cs
+++ b/Emby.Server.Implementations/Plugins/PluginManager.cs
@@ -5,6 +5,7 @@ using System.IO;
 using System.Linq;
 using System.Net.Http;
 using System.Reflection;
+using System.Runtime.Loader;
 using System.Text;
 using System.Text.Json;
 using System.Threading.Tasks;
@@ -30,6 +31,7 @@ namespace Emby.Server.Implementations.Plugins
     {
         private readonly string _pluginsPath;
         private readonly Version _appVersion;
+        private readonly AssemblyLoadContext _assemblyLoadContext;
         private readonly JsonSerializerOptions _jsonOptions;
         private readonly ILogger<PluginManager> _logger;
         private readonly IApplicationHost _appHost;
@@ -76,6 +78,8 @@ namespace Emby.Server.Implementations.Plugins
             _appHost = appHost;
             _minimumVersion = new Version(0, 0, 0, 1);
             _plugins = Directory.Exists(_pluginsPath) ? DiscoverPlugins().ToList() : new List<LocalPlugin>();
+
+            _assemblyLoadContext = new AssemblyLoadContext("PluginContext", true);
         }
 
         private IHttpClientFactory HttpClientFactory
@@ -124,7 +128,7 @@ namespace Emby.Server.Implementations.Plugins
                     Assembly assembly;
                     try
                     {
-                        assembly = Assembly.LoadFrom(file);
+                        assembly = _assemblyLoadContext.LoadFromAssemblyPath(file);
 
                         // Load all required types to verify that the plugin will load
                         assembly.GetTypes();
@@ -156,6 +160,12 @@ namespace Emby.Server.Implementations.Plugins
             }
         }
 
+        /// <inheritdoc />
+        public void UnloadAssemblies()
+        {
+            _assemblyLoadContext.Unload();
+        }
+
         /// <summary>
         /// Creates all the plugin instances.
         /// </summary>
diff --git a/Jellyfin.Server/Program.cs b/Jellyfin.Server/Program.cs
index b817ea6275..dded20347b 100644
--- a/Jellyfin.Server/Program.cs
+++ b/Jellyfin.Server/Program.cs
@@ -12,6 +12,7 @@ using Jellyfin.Server.Extensions;
 using Jellyfin.Server.Helpers;
 using Jellyfin.Server.Implementations;
 using MediaBrowser.Common.Configuration;
+using MediaBrowser.Controller;
 using Microsoft.EntityFrameworkCore;
 using Microsoft.Extensions.Configuration;
 using Microsoft.Extensions.DependencyInjection;
@@ -40,8 +41,9 @@ namespace Jellyfin.Server
         /// </summary>
         public const string LoggingConfigFileSystem = "logging.json";
 
-        private static readonly CancellationTokenSource _tokenSource = new CancellationTokenSource();
         private static readonly ILoggerFactory _loggerFactory = new SerilogLoggerFactory();
+        private static CancellationTokenSource _tokenSource = new();
+        private static long _startTimestamp;
         private static ILogger _logger = NullLogger.Instance;
         private static bool _restartOnShutdown;
 
@@ -86,11 +88,11 @@ namespace Jellyfin.Server
 
         private static async Task StartApp(StartupOptions options)
         {
-            var startTimestamp = Stopwatch.GetTimestamp();
+            _startTimestamp = Stopwatch.GetTimestamp();
 
             // Log all uncaught exceptions to std error
             static void UnhandledExceptionToConsole(object sender, UnhandledExceptionEventArgs e) =>
-                Console.Error.WriteLine("Unhandled Exception\n" + e.ExceptionObject.ToString());
+                Console.Error.WriteLine("Unhandled Exception\n" + e.ExceptionObject);
             AppDomain.CurrentDomain.UnhandledException += UnhandledExceptionToConsole;
 
             ServerApplicationPaths appPaths = StartupHelpers.CreateApplicationPaths(options);
@@ -151,14 +153,14 @@ namespace Jellyfin.Server
             // If hosting the web client, validate the client content path
             if (startupConfig.HostWebClient())
             {
-                string? webContentPath = appPaths.WebPath;
+                var webContentPath = appPaths.WebPath;
                 if (!Directory.Exists(webContentPath) || !Directory.EnumerateFiles(webContentPath).Any())
                 {
                     _logger.LogError(
                         "The server is expected to host the web client, but the provided content directory is either " +
                         "invalid or empty: {WebContentPath}. If you do not want to host the web client with the " +
                         "server, you may set the '--nowebclient' command line flag, or set" +
-                        "'{ConfigKey}=false' in your config settings.",
+                        "'{ConfigKey}=false' in your config settings",
                         webContentPath,
                         HostWebClientKey);
                     Environment.ExitCode = 1;
@@ -169,15 +171,31 @@ namespace Jellyfin.Server
             StartupHelpers.PerformStaticInitialization();
             Migrations.MigrationRunner.RunPreStartup(appPaths, _loggerFactory);
 
+            do
+            {
+                _restartOnShutdown = false;
+                await StartServer(appPaths, options, startupConfig).ConfigureAwait(false);
+
+                if (_restartOnShutdown)
+                {
+                    _tokenSource = new CancellationTokenSource();
+                    _startTimestamp = Stopwatch.GetTimestamp();
+                }
+            } while (_restartOnShutdown);
+        }
+
+        private static async Task StartServer(IServerApplicationPaths appPaths, StartupOptions options, IConfiguration startupConfig)
+        {
             var appHost = new CoreAppHost(
                 appPaths,
                 _loggerFactory,
                 options,
                 startupConfig);
 
+            IHost? host = null;
             try
             {
-                var host = Host.CreateDefaultBuilder()
+                host = Host.CreateDefaultBuilder()
                     .ConfigureServices(services => appHost.Init(services))
                     .ConfigureWebHostDefaults(webHostBuilder => webHostBuilder.ConfigureWebHostBuilder(appHost, startupConfig, appPaths, _logger))
                     .ConfigureAppConfiguration(config => config.ConfigureAppConfiguration(options, appPaths, startupConfig))
@@ -203,13 +221,13 @@ namespace Jellyfin.Server
                 }
                 catch (Exception ex) when (ex is not TaskCanceledException)
                 {
-                    _logger.LogError("Kestrel failed to start! This is most likely due to an invalid address or port bind - correct your bind configuration in network.xml and try again.");
+                    _logger.LogError("Kestrel failed to start! This is most likely due to an invalid address or port bind - correct your bind configuration in network.xml and try again");
                     throw;
                 }
 
                 await appHost.RunStartupTasksAsync(_tokenSource.Token).ConfigureAwait(false);
 
-                _logger.LogInformation("Startup complete {Time:g}", Stopwatch.GetElapsedTime(startTimestamp));
+                _logger.LogInformation("Startup complete {Time:g}", Stopwatch.GetElapsedTime(_startTimestamp));
 
                 // Block main thread until shutdown
                 await Task.Delay(-1, _tokenSource.Token).ConfigureAwait(false);
@@ -220,7 +238,7 @@ namespace Jellyfin.Server
             }
             catch (Exception ex)
             {
-                _logger.LogCritical(ex, "Error while starting server.");
+                _logger.LogCritical(ex, "Error while starting server");
             }
             finally
             {
@@ -240,11 +258,7 @@ namespace Jellyfin.Server
                 }
 
                 await appHost.DisposeAsync().ConfigureAwait(false);
-            }
-
-            if (_restartOnShutdown)
-            {
-                StartNewInstance(options);
+                host?.Dispose();
             }
         }
 
@@ -282,44 +296,5 @@ namespace Jellyfin.Server
                 .AddEnvironmentVariables("JELLYFIN_")
                 .AddInMemoryCollection(commandLineOpts.ConvertToConfig());
         }
-
-        private static void StartNewInstance(StartupOptions options)
-        {
-            _logger.LogInformation("Starting new instance");
-
-            var module = options.RestartPath;
-
-            if (string.IsNullOrWhiteSpace(module))
-            {
-                module = Environment.GetCommandLineArgs()[0];
-            }
-
-            string commandLineArgsString;
-            if (options.RestartArgs is not null)
-            {
-                commandLineArgsString = options.RestartArgs;
-            }
-            else
-            {
-                commandLineArgsString = string.Join(
-                    ' ',
-                    Environment.GetCommandLineArgs().Skip(1).Select(NormalizeCommandLineArgument));
-            }
-
-            _logger.LogInformation("Executable: {0}", module);
-            _logger.LogInformation("Arguments: {0}", commandLineArgsString);
-
-            Process.Start(module, commandLineArgsString);
-        }
-
-        private static string NormalizeCommandLineArgument(string arg)
-        {
-            if (!arg.Contains(' ', StringComparison.Ordinal))
-            {
-                return arg;
-            }
-
-            return "\"" + arg + "\"";
-        }
     }
 }
diff --git a/Jellyfin.Server/StartupOptions.cs b/Jellyfin.Server/StartupOptions.cs
index 0d9f379e0e..c3989751ca 100644
--- a/Jellyfin.Server/StartupOptions.cs
+++ b/Jellyfin.Server/StartupOptions.cs
@@ -63,14 +63,6 @@ namespace Jellyfin.Server
         [Option("package-name", Required = false, HelpText = "Used when packaging Jellyfin (example, synology).")]
         public string? PackageName { get; set; }
 
-        /// <inheritdoc />
-        [Option("restartpath", Required = false, HelpText = "Path to restart script.")]
-        public string? RestartPath { get; set; }
-
-        /// <inheritdoc />
-        [Option("restartargs", Required = false, HelpText = "Arguments for restart script.")]
-        public string? RestartArgs { get; set; }
-
         /// <inheritdoc />
         [Option("published-server-url", Required = false, HelpText = "Jellyfin Server URL to publish via auto discover process")]
         public string? PublishedServerUrl { get; set; }
diff --git a/MediaBrowser.Common/IApplicationHost.cs b/MediaBrowser.Common/IApplicationHost.cs
index 53683cdbdf..96ee701b38 100644
--- a/MediaBrowser.Common/IApplicationHost.cs
+++ b/MediaBrowser.Common/IApplicationHost.cs
@@ -47,12 +47,6 @@ namespace MediaBrowser.Common
         /// <value><c>true</c> if this instance is shutting down; otherwise, <c>false</c>.</value>
         bool IsShuttingDown { get; }
 
-        /// <summary>
-        /// Gets a value indicating whether this instance can self restart.
-        /// </summary>
-        /// <value><c>true</c> if this instance can self restart; otherwise, <c>false</c>.</value>
-        bool CanSelfRestart { get; }
-
         /// <summary>
         /// Gets the application version.
         /// </summary>
diff --git a/MediaBrowser.Common/Plugins/IPluginManager.cs b/MediaBrowser.Common/Plugins/IPluginManager.cs
index 176bcbbd54..fa92d383a2 100644
--- a/MediaBrowser.Common/Plugins/IPluginManager.cs
+++ b/MediaBrowser.Common/Plugins/IPluginManager.cs
@@ -29,6 +29,11 @@ namespace MediaBrowser.Common.Plugins
         /// <returns>An IEnumerable{Assembly}.</returns>
         IEnumerable<Assembly> LoadAssemblies();
 
+        /// <summary>
+        /// Unloads all of the assemblies.
+        /// </summary>
+        void UnloadAssemblies();
+
         /// <summary>
         /// Registers the plugin's services with the DI.
         /// Note: DI is not yet instantiated yet.