diff --git a/build/package/winget/Tgstation.Server.Host.Service.Wix.Extensions/InstallationExtensions.cs b/build/package/winget/Tgstation.Server.Host.Service.Wix.Extensions/InstallationExtensions.cs
index baee0364b0..d6a46b7700 100644
--- a/build/package/winget/Tgstation.Server.Host.Service.Wix.Extensions/InstallationExtensions.cs
+++ b/build/package/winget/Tgstation.Server.Host.Service.Wix.Extensions/InstallationExtensions.cs
@@ -1,6 +1,7 @@
 namespace Tgstation.Server.Host.Service.Wix.Extensions
 {
 	using System;
+	using System.IO;
 	using System.ServiceProcess;
 
 	using Tgstation.Server.Host.Common;
@@ -12,6 +13,12 @@
 	/// </summary>
 	public static class InstallationExtensions
 	{
+		/// <summary>
+		/// Package name
+		/// </summary>
+		/// <remarks>As much as I'd like to use Tgstation.Server.Common.Constants.CanonicalPackageName here, attempting to reference it makes Tgstation.Server.Migrator.Comms fail due to referencing the net2.0 version of that library. EVEN THOUGH IT'S A TRANSITIVE DEPENDENCY OF Tgstation.Server.Client!!!!! If that dead-ass tool has been removed, feel free to do this.</remarks>
+		const string CanonicalPackageName = "tgstation-server";
+
 		/// <summary>
 		/// Attempts to detach stop the existing tgstation-server service if it exists.
 		/// </summary>
@@ -28,9 +35,6 @@
 				session.Log("Begin DetachStopTgsServiceIfRunning");
 				ServiceController serviceController = null;
 
-				// As much as I'd like to use Tgstation.Server.Common.Constants.CanonicalPackageName here, attempting to reference it make Tgstation.Server.Migrator.Comms fail due to referencing the net2.0 version of that library. EVEN THOUGH IT'S A TRANSITIVE DEPENDENCY OF Tgstation.Server.Client!!!!!
-				// If that dead-ass tool has been removed, feel free to do this
-				const string CanonicalPackageName = "tgstation-server";
 				session.Log($"Searching for {CanonicalPackageName} service...");
 				try
 				{
@@ -76,5 +80,55 @@
 				return ActionResult.Failure;
 			}
 		}
+
+		/// <summary>
+		/// Attempts to copy the initial config to the production config if necessary.
+		/// </summary>
+		/// <param name="session">The installer <see cref="Session"/>.</param>
+		/// <returns>The <see cref="ActionResult"/> of the custom action.</returns>
+		[CustomAction]
+		public static ActionResult ApplyProductionAppsettingsIfNonExistant(Session session)
+		{
+			if (session == null)
+				throw new ArgumentNullException(nameof(session));
+
+			try
+			{
+				session.Log("Begin ApplyProductionAppsettingsIfNonExistant");
+				var programDataDirectory = Path.Combine(
+					Environment.GetFolderPath(Environment.SpecialFolder.CommonApplicationData),
+					CanonicalPackageName);
+				var initialAppSettingsPath = Path.Combine(programDataDirectory, "appsettings.Initial.yml");
+				var productionAppSettingsPath = Path.Combine(programDataDirectory, "appsettings.Production.yml");
+
+				var initialAppSettingsExists = File.Exists(initialAppSettingsPath);
+				var productionAppSettingsExists = File.Exists(productionAppSettingsPath);
+
+				if (productionAppSettingsExists)
+					session.Log("appsettings.Production.yml present");
+				else
+					session.Log("appsettings.Production.yml NOT present");
+
+				if (!initialAppSettingsExists)
+					session.Log("appsettings.Initial.yml NOT present!");
+				else
+				{
+					session.Log("appsettings.Initial.yml present");
+					if (!productionAppSettingsExists)
+					{
+						session.Log("Copying initial settings to production settings...");
+						File.Copy(initialAppSettingsPath, productionAppSettingsPath);
+						return ActionResult.Success;
+					}
+				}
+
+				return ActionResult.NotExecuted;
+			}
+			catch (Exception ex)
+			{
+				session.Log($"Exception in ApplyProductionAppsettingsIfNonExistant:{Environment.NewLine}{ex}");
+				return ActionResult.Failure;
+			}
+		}
 	}
 }
diff --git a/build/package/winget/Tgstation.Server.Host.Service.Wix/Package.wxs b/build/package/winget/Tgstation.Server.Host.Service.Wix/Package.wxs
index f6897aab0f..95da39d252 100644
--- a/build/package/winget/Tgstation.Server.Host.Service.Wix/Package.wxs
+++ b/build/package/winget/Tgstation.Server.Host.Service.Wix/Package.wxs
@@ -7,6 +7,7 @@
     <Binary Id="InstallerExtensionsBinary" SourceFile="$(var.Tgstation.Server.Host.Service.Wix.Extensions.TargetName).CA.dll" />
 
     <CustomAction Id="DetachStopTgsServiceIfRunningAction" BinaryRef="InstallerExtensionsBinary" DllEntry="DetachStopTgsServiceIfRunning" Execute="deferred" />
+    <CustomAction Id="ApplyProductionAppsettingsIfNonExistantAction" BinaryRef="InstallerExtensionsBinary" DllEntry="ApplyProductionAppsettingsIfNonExistant" Execute="deferred" />
     <CustomAction Id="RunTgsConfigure" Execute="deferred" FileRef="ServiceExecutableFile" ExeCommand="-c -p=--appsettings-base-path=[APPLICATIONDATADIRECTORY]" />
     <CustomAction Id="RunTgsConfigureMariaDB" Execute="deferred" FileRef="ServiceExecutableFile" ExeCommand="-c -p=&quot;--appsettings-base-path=[APPLICATIONDATADIRECTORY] --Internal:MariaDBSetup=true --Internal:MariaDBDefaultRootPassword=\&quot;[MARIADB_PASSWORD]\&quot;&quot;" />
 
@@ -16,6 +17,7 @@
 
     <InstallExecuteSequence>
       <Custom Action="DetachStopTgsServiceIfRunningAction" Condition="UPGRADINGPRODUCTCODE OR REINSTALL" Before="StopServices" />
+      <Custom Action="ApplyProductionAppsettingsIfNonExistantAction" Condition="NOT ((NOT REMOVE~=&quot;ALL&quot;) AND (NOT PRODUCTIONAPPSETTINGSPRESENT) AND ((WIX_BOOTSTRAPPER_UILEVEL >= 4) OR (UILevel >= 4)))" Before="StartServices" />
       <Custom Action="RunTgsConfigure" Before="StartServices" Condition="(NOT MARIADB_INSTALLED) AND (NOT REMOVE~=&quot;ALL&quot;) AND (NOT PRODUCTIONAPPSETTINGSPRESENT) AND ((WIX_BOOTSTRAPPER_UILEVEL >= 4) OR (UILevel >= 4))"/>
       <Custom Action="RunTgsConfigureMariaDB" Before="StartServices" Condition="MARIADB_INSTALLED AND (NOT REMOVE~=&quot;ALL&quot;) AND (NOT PRODUCTIONAPPSETTINGSPRESENT) AND ((WIX_BOOTSTRAPPER_UILEVEL >= 4) OR (UILevel >= 4))"/>
       <StartServices Condition="(NOT REMOVE~=&quot;ALL&quot;) AND ((WIX_BOOTSTRAPPER_UILEVEL >= 4) OR (UILevel >= 4) OR PRODUCTIONAPPSETTINGSPRESENT)"/>
@@ -79,7 +81,7 @@
           <File Source="../../../../src/Tgstation.Server.Host/appsettings.yml" />
         </Component>
         <Component Id="ProductionAppSettingsComponent" Guid="" NeverOverwrite="yes">
-          <File Source="../../appsettings.Initial.yml" Name="appsettings.Production.yml">
+          <File Source="../../appsettings.Initial.yml">
             <PermissionEx Sddl="D:PAI(A;;FA;;;SY)(A;;FA;;;BA)" />
           </File>
         </Component>