diff --git a/Jellyfin.Server/Migrations/MigrationRunner.cs b/Jellyfin.Server/Migrations/MigrationRunner.cs
index caaa58ae15..ac7f3d77ae 100644
--- a/Jellyfin.Server/Migrations/MigrationRunner.cs
+++ b/Jellyfin.Server/Migrations/MigrationRunner.cs
@@ -15,7 +15,8 @@ namespace Jellyfin.Server.Migrations
         /// </summary>
         internal static readonly IUpdater[] Migrations =
         {
-            new Routines.DisableTranscodingThrottling()
+            new Routines.DisableTranscodingThrottling(),
+            new Routines.CreateUserLoggingConfigFile()
         };
 
         /// <summary>
diff --git a/Jellyfin.Server/Migrations/Routines/CreateUserLoggingConfigFile.cs b/Jellyfin.Server/Migrations/Routines/CreateUserLoggingConfigFile.cs
new file mode 100644
index 0000000000..7a089680e4
--- /dev/null
+++ b/Jellyfin.Server/Migrations/Routines/CreateUserLoggingConfigFile.cs
@@ -0,0 +1,93 @@
+using System;
+using System.Collections.Generic;
+using System.IO;
+using System.Linq;
+using MediaBrowser.Common.Configuration;
+using Microsoft.Extensions.Logging;
+using Newtonsoft.Json.Linq;
+
+namespace Jellyfin.Server.Migrations.Routines
+{
+    /// <summary>
+    /// Migration to initialize the user logging configuration file "logging.user.json".
+    /// If the deprecated logging.json file exists and has a custom config, it will be used as logging.user.json,
+    /// otherwise a blank file will be created.
+    /// </summary>
+    internal class CreateUserLoggingConfigFile : IUpdater
+    {
+        /// <summary>
+        /// An empty logging JSON configuration, which will be used as the default contents for the user settings config file.
+        /// </summary>
+        private const string EmptyLoggingConfig = @"{ ""Serilog"": { } }";
+
+        /// <summary>
+        /// File history for logging.json as existed during this migration creation. The contents for each has been minified.
+        /// </summary>
+        private readonly List<string> _defaultConfigHistory = new List<string>
+        {
+            // 9a6c27947353585391e211aa88b925f81e8cd7b9
+            @"{""Serilog"":{""MinimumLevel"":{""Default"":""Information"",""Override"":{""Microsoft"":""Warning"",""System"":""Warning""}},""WriteTo"":[{""Name"":""Console"",""Args"":{""outputTemplate"":""[{Timestamp:HH:mm:ss}] [{Level:u3}] [{ThreadId}] {SourceContext}: {Message:lj}{NewLine}{Exception}""}},{""Name"":""Async"",""Args"":{""configure"":[{""Name"":""File"",""Args"":{""path"":""%JELLYFIN_LOG_DIR%//log_.log"",""rollingInterval"":""Day"",""retainedFileCountLimit"":3,""rollOnFileSizeLimit"":true,""fileSizeLimitBytes"":100000000,""outputTemplate"":""[{Timestamp:yyyy-MM-dd HH:mm:ss.fff zzz}] [{Level:u3}] [{ThreadId}] {SourceContext}: {Message}{NewLine}{Exception}""}}]}}],""Enrich"":[""FromLogContext"",""WithThreadId""]}}",
+            // 71bdcd730705a714ee208eaad7290b7c68df3885
+            @"{""Serilog"":{""MinimumLevel"":""Information"",""WriteTo"":[{""Name"":""Console"",""Args"":{""outputTemplate"":""[{Timestamp:HH:mm:ss}] [{Level:u3}] [{ThreadId}] {SourceContext}: {Message:lj}{NewLine}{Exception}""}},{""Name"":""Async"",""Args"":{""configure"":[{""Name"":""File"",""Args"":{""path"":""%JELLYFIN_LOG_DIR%//log_.log"",""rollingInterval"":""Day"",""retainedFileCountLimit"":3,""rollOnFileSizeLimit"":true,""fileSizeLimitBytes"":100000000,""outputTemplate"":""[{Timestamp:yyyy-MM-dd HH:mm:ss.fff zzz}] [{Level:u3}] [{ThreadId}] {SourceContext}: {Message}{NewLine}{Exception}""}}]}}],""Enrich"":[""FromLogContext"",""WithThreadId""]}}",
+            // a44936f97f8afc2817d3491615a7cfe1e31c251c
+            @"{""Serilog"":{""MinimumLevel"":""Information"",""WriteTo"":[{""Name"":""Console"",""Args"":{""outputTemplate"":""[{Timestamp:HH:mm:ss}] [{Level:u3}] {Message:lj}{NewLine}{Exception}""}},{""Name"":""File"",""Args"":{""path"":""%JELLYFIN_LOG_DIR%//log_.log"",""rollingInterval"":""Day"",""outputTemplate"":""[{Timestamp:yyyy-MM-dd HH:mm:ss.fff zzz}] [{Level:u3}] {Message}{NewLine}{Exception}""}}]}}",
+            // 7af3754a11ad5a4284f107997fb5419a010ce6f3
+            @"{""Serilog"":{""MinimumLevel"":""Information"",""WriteTo"":[{""Name"":""Console"",""Args"":{""outputTemplate"":""[{Timestamp:HH:mm:ss}] [{Level:u3}] {Message:lj}{NewLine}{Exception}""}},{""Name"":""Async"",""Args"":{""configure"":[{""Name"":""File"",""Args"":{""path"":""%JELLYFIN_LOG_DIR%//log_.log"",""rollingInterval"":""Day"",""outputTemplate"":""[{Timestamp:yyyy-MM-dd HH:mm:ss.fff zzz}] [{Level:u3}] {Message}{NewLine}{Exception}""}}]}}]}}",
+            // 60691349a11f541958e0b2247c9abc13cb40c9fb
+            @"{""Serilog"":{""MinimumLevel"":""Information"",""WriteTo"":[{""Name"":""Console"",""Args"":{""outputTemplate"":""[{Timestamp:HH:mm:ss}] [{Level:u3}] {Message:lj}{NewLine}{Exception}""}},{""Name"":""Async"",""Args"":{""configure"":[{""Name"":""File"",""Args"":{""path"":""%JELLYFIN_LOG_DIR%//log_.log"",""rollingInterval"":""Day"",""retainedFileCountLimit"":3,""rollOnFileSizeLimit"":true,""fileSizeLimitBytes"":100000000,""outputTemplate"":""[{Timestamp:yyyy-MM-dd HH:mm:ss.fff zzz}] [{Level:u3}] {Message}{NewLine}{Exception}""}}]}}]}}",
+            // 65fe243afbcc4b596cf8726708c1965cd34b5f68
+            @"{""Serilog"":{""MinimumLevel"":""Information"",""WriteTo"":[{""Name"":""Console"",""Args"":{""outputTemplate"":""[{Timestamp:HH:mm:ss}] [{Level:u3}] {ThreadId} {SourceContext}: {Message:lj} {NewLine}{Exception}""}},{""Name"":""Async"",""Args"":{""configure"":[{""Name"":""File"",""Args"":{""path"":""%JELLYFIN_LOG_DIR%//log_.log"",""rollingInterval"":""Day"",""retainedFileCountLimit"":3,""rollOnFileSizeLimit"":true,""fileSizeLimitBytes"":100000000,""outputTemplate"":""[{Timestamp:yyyy-MM-dd HH:mm:ss.fff zzz}] [{Level:u3}] {ThreadId} {SourceContext}:{Message} {NewLine}{Exception}""}}]}}],""Enrich"":[""FromLogContext"",""WithThreadId""]}}",
+            // 96c9af590494aa8137d5a061aaf1e68feee60b67
+            @"{""Serilog"":{""MinimumLevel"":""Information"",""WriteTo"":[{""Name"":""Console"",""Args"":{""outputTemplate"":""[{Timestamp:HH:mm:ss}] [{Level:u3}] [{ThreadId}] {SourceContext}: {Message:lj}{NewLine}{Exception}""}},{""Name"":""Async"",""Args"":{""configure"":[{""Name"":""File"",""Args"":{""path"":""%JELLYFIN_LOG_DIR%//log_.log"",""rollingInterval"":""Day"",""retainedFileCountLimit"":3,""rollOnFileSizeLimit"":true,""fileSizeLimitBytes"":100000000,""outputTemplate"":""[{Timestamp:yyyy-MM-dd HH:mm:ss.fff zzz}] [{Level:u3}] [{ThreadId}] {SourceContext}:{Message}{NewLine}{Exception}""}}]}}],""Enrich"":[""FromLogContext"",""WithThreadId""]}}",
+        };
+
+        /// <inheritdoc/>
+        public string Name => "CreateLoggingConfigHeirarchy";
+
+        /// <inheritdoc/>
+        public void Perform(CoreAppHost host, ILogger logger)
+        {
+            var logDirectory = host.Resolve<IApplicationPaths>().ConfigurationDirectoryPath;
+            var oldConfigPath = Path.Combine(logDirectory, "logging.json");
+            var userConfigPath = Path.Combine(logDirectory, Program.LoggingConfigFileUser);
+
+            // Check if there are existing settings in the old "logging.json" file that should be migrated
+            bool shouldMigrateOldFile = ShouldKeepOldConfig(oldConfigPath);
+
+            // Create the user settings file "logging.user.json"
+            if (shouldMigrateOldFile)
+            {
+                // Use the existing logging.json file
+                File.Copy(oldConfigPath, userConfigPath);
+            }
+            else
+            {
+                // Write an empty JSON file
+                File.WriteAllText(userConfigPath, EmptyLoggingConfig);
+            }
+        }
+
+        /// <summary>
+        /// Check if the existing logging.json file should be migrated to logging.user.json.
+        /// </summary>
+        private bool ShouldKeepOldConfig(string oldConfigPath)
+        {
+            // Cannot keep the old logging file if it doesn't exist
+            if (!File.Exists(oldConfigPath))
+            {
+                return false;
+            }
+
+            // Check if the existing logging.json file has been modified by the user by comparing it to all the
+            // versions in our git history. Until now, the file has never been migrated after first creation so users
+            // could have any version from the git history.
+            var existingConfigJson = JToken.Parse(File.ReadAllText(oldConfigPath));
+            var existingConfigIsUnmodified = _defaultConfigHistory
+                .Select(historicalConfigText => JToken.Parse(historicalConfigText))
+                .Any(historicalConfigJson => JToken.DeepEquals(existingConfigJson, historicalConfigJson));
+
+            // The existing config file should be kept and used only if it has been modified by the user
+            return !existingConfigIsUnmodified;
+        }
+    }
+}
diff --git a/Jellyfin.Server/Migrations/Routines/DisableZealousLogging.cs b/Jellyfin.Server/Migrations/Routines/DisableZealousLogging.cs
deleted file mode 100644
index 501f8f8654..0000000000
--- a/Jellyfin.Server/Migrations/Routines/DisableZealousLogging.cs
+++ /dev/null
@@ -1,29 +0,0 @@
-using System;
-using System.IO;
-using MediaBrowser.Common.Configuration;
-using MediaBrowser.Model.Configuration;
-using Microsoft.Extensions.Configuration;
-using Microsoft.Extensions.Logging;
-using Serilog;
-using ILogger = Microsoft.Extensions.Logging.ILogger;
-
-namespace Jellyfin.Server.Migrations.Routines
-{
-    /// <summary>
-    /// Updater that takes care of bringing configuration up to 10.5.0 standards.
-    /// </summary>
-    internal class DisableZealousLogging : IUpdater
-    {
-        /// <inheritdoc/>
-        public string Name => "DisableZealousLogging";
-
-        /// <inheritdoc/>
-        // This tones down logging from some components
-        public void Perform(CoreAppHost host, ILogger logger)
-        {
-            string configPath = Path.Combine(host.ServerConfigurationManager.ApplicationPaths.ConfigurationDirectoryPath, Program.LoggingConfigFile);
-            // TODO: fix up the config
-            throw new NotImplementedException("don't know how to fix logging yet");
-        }
-    }
-}