diff --git a/TGServerService/Service.cs b/TGServerService/Service.cs
index b9d8547453..13b1605af9 100644
--- a/TGServerService/Service.cs
+++ b/TGServerService/Service.cs
@@ -214,8 +214,6 @@ namespace TGServerService
 			{
 				var newVersion = Config.SettingsVersion;
 				Config.Upgrade();
-
-				PrePrepConfig();
 				
 				for (var oldVersion = Config.SettingsVersion; oldVersion < newVersion; ++oldVersion)
 					MigrateSettings(oldVersion);
@@ -225,6 +223,8 @@ namespace TGServerService
 				Config.UpgradeRequired = false;
 				Config.Save();
 			}
+
+			PrePrepConfig();
 		}
 
 		/// <summary>
diff --git a/TGServiceTests/Service/TestService.cs b/TGServiceTests/Service/TestService.cs
index 43d6f277f6..8c19056596 100644
--- a/TGServiceTests/Service/TestService.cs
+++ b/TGServiceTests/Service/TestService.cs
@@ -19,10 +19,9 @@ namespace TGServerService.Tests
 		}
 
 		/// <summary>
-		/// Test <see cref="Service.OnStart(string[])"/> and <see cref="Service.OnStop"/> can execute successfully
+		/// Starts and stops a <see cref="Service"/>
 		/// </summary>
-		[TestMethod]
-		public void TestStartupAndShutdown()
+		void StartStopServiceBasic()
 		{
 			using (var S = new ServiceAccessor())
 			{
@@ -30,6 +29,15 @@ namespace TGServerService.Tests
 				S.FakeStop();
 			}
 		}
+
+		/// <summary>
+		/// Test <see cref="Service.OnStart(string[])"/> and <see cref="Service.OnStop"/> can execute successfully
+		/// </summary>
+		[TestMethod]
+		public void TestStartupAndShutdown()
+		{
+			StartStopServiceBasic();
+		}
 		
 		/// <summary>
 		/// Test <see cref="Service.OnStart(string[])"/> and <see cref="Service.OnStop"/> can execute successfully with a commandline port override
@@ -37,11 +45,29 @@ namespace TGServerService.Tests
 		[TestMethod]
 		public void TestCommandLinePortSet()
 		{
+			Properties.Settings.Default.RemoteAccessPort = 11111;
 			using (var S = new ServiceAccessor())
 			{
 				S.FakeStart(new string[] { "-port", "36785" });
 				S.FakeStop();
 			}
+			Assert.AreEqual(Properties.Settings.Default.RemoteAccessPort, 36785);
+		}
+
+		/// <summary>
+		/// Test that the .NET config is always initialized regardless of <see cref="Properties.Settings.UpgradeRequired"/>
+		/// </summary>
+		[TestMethod]
+		public void TestNETConfigIsAlwaysPrepped()
+		{
+			Properties.Settings.Default.UpgradeRequired = true;
+			Properties.Settings.Default.InstancePaths = null;
+			StartStopServiceBasic();
+			Assert.IsNotNull(Properties.Settings.Default.InstancePaths);
+			Properties.Settings.Default.UpgradeRequired = false;
+			Properties.Settings.Default.InstancePaths = null;
+			StartStopServiceBasic();
+			Assert.IsNotNull(Properties.Settings.Default.InstancePaths);
 		}
 	}
 }