diff --git a/src/Tgstation.Server.Host/Setup/SetupWizard.cs b/src/Tgstation.Server.Host/Setup/SetupWizard.cs
index 15f2b82e48..775cbe98e0 100644
--- a/src/Tgstation.Server.Host/Setup/SetupWizard.cs
+++ b/src/Tgstation.Server.Host/Setup/SetupWizard.cs
@@ -5,6 +5,7 @@ using System.Data.SqlClient;
 using System.Globalization;
 using System.IO;
 using System.Linq;
+using System.Net;
 using System.Text;
 using System.Text.RegularExpressions;
 using System.Threading;
@@ -141,19 +142,29 @@ namespace Tgstation.Server.Host.Setup
 		/// A prompt for a yes or no value.
 		/// </summary>
 		/// <param name="question">The question <see cref="string"/>.</param>
+		/// <param name="defaultResponse">The optional default response if the user doesn't enter anything.</param>
 		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation.</param>
 		/// <returns>A <see cref="Task"/> resulting in <see langword="true"/> if the user replied yes, <see langword="false"/> otherwise.</returns>
-		async Task<bool> PromptYesNo(string question, CancellationToken cancellationToken)
+		async Task<bool> PromptYesNo(string question, bool? defaultResponse, CancellationToken cancellationToken)
 		{
 			do
 			{
-				await console.WriteAsync(question, false, cancellationToken);
+				await console.WriteAsync($"{question} ({(defaultResponse == true ? 'Y' : 'y')}/{(defaultResponse == false ? 'N' : 'n')}): ", false, cancellationToken);
 				var responseString = await console.ReadLineAsync(false, cancellationToken);
-				var upperResponse = responseString.ToUpperInvariant();
-				if (upperResponse == "Y" || upperResponse == "YES")
-					return true;
-				else if (upperResponse == "N" || upperResponse == "NO")
-					return false;
+				if (responseString.Length == 0)
+				{
+					if (defaultResponse.HasValue)
+						return defaultResponse.Value;
+				}
+				else
+				{
+					var upperResponse = responseString.ToUpperInvariant();
+					if (upperResponse == "Y" || upperResponse == "YES")
+						return true;
+					else if (upperResponse == "N" || upperResponse == "NO")
+						return false;
+				}
+
 				await console.WriteAsync("Invalid response!", true, cancellationToken);
 			}
 			while (true);
@@ -316,7 +327,8 @@ namespace Tgstation.Server.Host.Setup
 				await console.WriteAsync("Note, this relative path (currently) resolves to the following:", true, cancellationToken);
 				await console.WriteAsync(resolvedPath, true, cancellationToken);
 				bool writeResolved = await PromptYesNo(
-					"Would you like to save the relative path in the configuration? If not, the full path will be saved. (y/n): ",
+					"Would you like to save the relative path in the configuration? If not, the full path will be saved.",
+					null,
 					cancellationToken);
 
 				if (writeResolved)
@@ -405,6 +417,7 @@ namespace Tgstation.Server.Host.Setup
 				ushort? serverPort = null;
 
 				bool isSqliteDB = databaseConfiguration.DatabaseType == DatabaseType.Sqlite;
+				IPHostEntry serverAddressEntry = null;
 				if (!isSqliteDB)
 					do
 					{
@@ -430,7 +443,20 @@ namespace Tgstation.Server.Host.Setup
 							}
 						}
 
-						break;
+						try
+						{
+							if (serverAddress != null)
+							{
+								await console.WriteAsync("Attempting to resolve address...", true, cancellationToken);
+								serverAddressEntry = await Dns.GetHostEntryAsync(serverAddress, cancellationToken);
+							}
+
+							break;
+						}
+						catch (Exception ex)
+						{
+							await console.WriteAsync($"Unable to resolve address: {ex.Message}", true, cancellationToken);
+						}
 					}
 					while (true);
 
@@ -451,7 +477,10 @@ namespace Tgstation.Server.Host.Setup
 								databaseName = await ValidateNonExistantSqliteDBName(databaseName, cancellationToken);
 						}
 						else
-							dbExists = await PromptYesNo("Does this database already exist? If not, we will attempt to CREATE it. (y/n): ", cancellationToken);
+							dbExists = await PromptYesNo(
+								"Does this database already exist? If not, we will attempt to CREATE it.",
+								null,
+								cancellationToken);
 					}
 
 					if (String.IsNullOrWhiteSpace(databaseName))
@@ -463,7 +492,12 @@ namespace Tgstation.Server.Host.Setup
 
 				bool useWinAuth;
 				if (databaseConfiguration.DatabaseType == DatabaseType.SqlServer && platformIdentifier.IsWindows)
-					useWinAuth = await PromptYesNo("Use Windows Authentication? (y/n): ", cancellationToken);
+				{
+					var defaultResponse = serverAddressEntry.AddressList.Any(IPAddress.IsLoopback)
+						? (bool?)true
+						: null;
+					useWinAuth = await PromptYesNo("Use Windows Authentication?", defaultResponse, cancellationToken);
+				}
 				else
 					useWinAuth = false;
 
@@ -648,7 +682,7 @@ namespace Tgstation.Server.Host.Setup
 			if (String.IsNullOrWhiteSpace(newGeneralConfiguration.GitHubAccessToken))
 				newGeneralConfiguration.GitHubAccessToken = null;
 
-			newGeneralConfiguration.HostApiDocumentation = await PromptYesNo("Host API Documentation? (y/n): ", cancellationToken);
+			newGeneralConfiguration.HostApiDocumentation = await PromptYesNo("Host API Documentation?", false, cancellationToken);
 
 			return newGeneralConfiguration;
 		}
@@ -662,7 +696,7 @@ namespace Tgstation.Server.Host.Setup
 		{
 			var fileLoggingConfiguration = new FileLoggingConfiguration();
 			await console.WriteAsync(null, true, cancellationToken);
-			fileLoggingConfiguration.Disable = !await PromptYesNo("Enable file logging? (y/n): ", cancellationToken);
+			fileLoggingConfiguration.Disable = !await PromptYesNo("Enable file logging?", true, cancellationToken);
 
 			if (!fileLoggingConfiguration.Disable)
 			{
@@ -747,7 +781,7 @@ namespace Tgstation.Server.Host.Setup
 		{
 			var elasticsearchConfiguration = new ElasticsearchConfiguration();
 			await console.WriteAsync(null, true, cancellationToken);
-			elasticsearchConfiguration.Enable = await PromptYesNo("Enable logging to an external ElasticSearch server? (y/n): ", cancellationToken);
+			elasticsearchConfiguration.Enable = await PromptYesNo("Enable logging to an external ElasticSearch server?", false, cancellationToken);
 
 			if (elasticsearchConfiguration.Enable)
 			{
@@ -797,8 +831,11 @@ namespace Tgstation.Server.Host.Setup
 		{
 			var config = new ControlPanelConfiguration
 			{
-				Enable = await PromptYesNo("Enable the web control panel? (y/n): ", cancellationToken),
-				AllowAnyOrigin = await PromptYesNo("Allow web control panels hosted elsewhere to access the server? (Access-Control-Allow-Origin: *) (y/n): ", cancellationToken),
+				Enable = await PromptYesNo("Enable the web control panel?", true, cancellationToken),
+				AllowAnyOrigin = await PromptYesNo(
+					"Allow web control panels hosted elsewhere to access the server? (Access-Control-Allow-Origin: *)",
+					true,
+					cancellationToken),
 			};
 
 			if (!config.AllowAnyOrigin)
@@ -822,7 +859,7 @@ namespace Tgstation.Server.Host.Setup
 		/// <returns>A <see cref="Task{TResult}"/> resulting in the new <see cref="SwarmConfiguration"/>.</returns>
 		async Task<SwarmConfiguration> ConfigureSwarm(CancellationToken cancellationToken)
 		{
-			var enable = await PromptYesNo("Enable swarm mode? (y/n): ", cancellationToken);
+			var enable = await PromptYesNo("Enable swarm mode?", false, cancellationToken);
 			if (!enable)
 				return null;
 
@@ -860,7 +897,7 @@ namespace Tgstation.Server.Host.Setup
 			}
 			while (String.IsNullOrWhiteSpace(privateKey));
 
-			var controller = await PromptYesNo("Is this server the swarm's controller? (y/n): ", cancellationToken);
+			var controller = await PromptYesNo("Is this server the swarm's controller? (y/n): ", null, cancellationToken);
 			Uri controllerAddress = null;
 			if (!controller)
 				controllerAddress = await ParseAddress("Enter the swarm controller's HTTP(S) address: ");
@@ -1065,7 +1102,7 @@ namespace Tgstation.Server.Host.Setup
 						{
 							await console.WriteAsync(String.Format(CultureInfo.InvariantCulture, "The configuration settings are requesting the setup wizard be run, but you already appear to have a configuration file ({0})!", userConfigFileName), true, cancellationToken);
 
-							forceRun = await PromptYesNo("Continue running setup wizard? (y/n): ", cancellationToken);
+							forceRun = await PromptYesNo("Continue running setup wizard?", false, cancellationToken);
 						}
 
 						if (!forceRun)
diff --git a/tests/Tgstation.Server.Host.Tests/Setup/TestSetupWizard.cs b/tests/Tgstation.Server.Host.Tests/Setup/TestSetupWizard.cs
index 841f97bfd1..8edbf59c70 100644
--- a/tests/Tgstation.Server.Host.Tests/Setup/TestSetupWizard.cs
+++ b/tests/Tgstation.Server.Host.Tests/Setup/TestSetupWizard.cs
@@ -152,14 +152,14 @@ namespace Tgstation.Server.Host.Setup.Tests
 				"666",
 				"FakeDBType",
 				nameof(DatabaseType.SqlServer),
-				"this isn't validated",
+				"localhost",
 				"nor is this",
 				"no",
 				//test winauth
 				"yes",
 				//sql server will always fail so reconfigure with maria
 				nameof(DatabaseType.MariaDB),
-				"bleh",
+				"127.0.0.1",
 				"blah",
 				"NO",
 				"user",
@@ -187,7 +187,7 @@ namespace Tgstation.Server.Host.Setup.Tests
 				String.Empty,
 				//test MySQL errors
 				nameof(DatabaseType.MySql),
-				String.Empty,
+				"::1",
 				String.Empty,
 				"DbName",
 				"n",