diff --git a/src/Service.Tests/Configuration/ConfigurationTests.cs b/src/Service.Tests/Configuration/ConfigurationTests.cs
index d1ecd6d0f6..5692311c73 100644
--- a/src/Service.Tests/Configuration/ConfigurationTests.cs
+++ b/src/Service.Tests/Configuration/ConfigurationTests.cs
@@ -9,6 +9,7 @@
 using System.Threading;
 using System.Threading.Tasks;
 using Azure.DataApiBuilder.Config;
+using Azure.DataApiBuilder.Service.AuthenticationHelpers;
 using Azure.DataApiBuilder.Service.Authorization;
 using Azure.DataApiBuilder.Service.Configurations;
 using Azure.DataApiBuilder.Service.Controllers;
@@ -810,6 +811,64 @@ public async Task TestPathRewriteMiddlewareForGraphQL(
             }
         }
 
+        /// <summary>
+        /// Tests that Startup.cs properly handles EasyAuth authentication configuration.
+        /// AppService as Identity Provider while in Production mode will result in startup error.
+        /// An Azure AppService environment has environment variables on the host which indicate
+        /// the environment is, in fact, an AppService environment.
+        /// </summary>
+        /// <param name="hostMode">HostMode in Runtime config - Development or Production.</param>
+        /// <param name="authType">EasyAuth auth type - AppService or StaticWebApps.</param>
+        /// <param name="setEnvVars">Whether to set the AppService host environment variables.</param>
+        /// <param name="expectError">Whether an error is expected.</param>
+        [DataTestMethod]
+        [TestCategory(TestCategory.MSSQL)]
+        [DataRow(HostModeType.Development, EasyAuthType.AppService, false, false, DisplayName = "AppService Dev - No EnvVars - No Error")]
+        [DataRow(HostModeType.Development, EasyAuthType.AppService, true, false, DisplayName = "AppService Dev - EnvVars - No Error")]
+        [DataRow(HostModeType.Production, EasyAuthType.AppService, false, true, DisplayName = "AppService Prod - No EnvVars - Error")]
+        [DataRow(HostModeType.Production, EasyAuthType.AppService, true, false, DisplayName = "AppService Prod - EnvVars - Error")]
+        [DataRow(HostModeType.Development, EasyAuthType.StaticWebApps, false, false, DisplayName = "SWA Dev - No EnvVars - No Error")]
+        [DataRow(HostModeType.Development, EasyAuthType.StaticWebApps, true, false, DisplayName = "SWA Dev - EnvVars - No Error")]
+        [DataRow(HostModeType.Production, EasyAuthType.StaticWebApps, false, false, DisplayName = "SWA Prod - No EnvVars - No Error")]
+        [DataRow(HostModeType.Production, EasyAuthType.StaticWebApps, true, false, DisplayName = "SWA Prod - EnvVars - No Error")]
+        public void TestProductionModeAppServiceEnvironmentCheck(HostModeType hostMode, EasyAuthType authType, bool setEnvVars, bool expectError)
+        {
+            // Clears or sets App Service Environment Variables based on test input.
+            Environment.SetEnvironmentVariable(AppServiceAuthenticationInfo.APPSERVICESAUTH_ENABLED_ENVVAR, setEnvVars ? "true" : null);
+            Environment.SetEnvironmentVariable(AppServiceAuthenticationInfo.APPSERVICESAUTH_IDENTITYPROVIDER_ENVVAR, setEnvVars ? "AzureActiveDirectory" : null);
+
+            RuntimeConfigProvider configProvider = TestHelper.GetRuntimeConfigProvider(MSSQL_ENVIRONMENT);
+            RuntimeConfig config = configProvider.GetRuntimeConfiguration();
+
+            // Setup configuration
+            AuthenticationConfig authenticationConfig = new(Provider: authType.ToString());
+            HostGlobalSettings customHostGlobalSettings = config.HostGlobalSettings with { Mode = hostMode, Authentication = authenticationConfig };
+            JsonElement serializedCustomHostGlobalSettings = JsonSerializer.SerializeToElement(customHostGlobalSettings, RuntimeConfig.SerializerOptions);
+            Dictionary<GlobalSettingsType, object> customRuntimeSettings = new(config.RuntimeSettings);
+            customRuntimeSettings.Remove(GlobalSettingsType.Host);
+            customRuntimeSettings.Add(GlobalSettingsType.Host, serializedCustomHostGlobalSettings);
+            RuntimeConfig configWithCustomHostMode = config with { RuntimeSettings = customRuntimeSettings };
+
+            const string CUSTOM_CONFIG = "custom-config.json";
+            File.WriteAllText(path: CUSTOM_CONFIG, contents: JsonSerializer.Serialize(configWithCustomHostMode, RuntimeConfig.SerializerOptions));
+            string[] args = new[]
+            {
+                $"--ConfigFileName={CUSTOM_CONFIG}"
+            };
+
+            // This test only checks for startup errors, so no requests are sent to the test server.
+            try
+            {
+                using TestServer server = new(Program.CreateWebHostBuilder(args));
+                Assert.IsFalse(expectError, message: "Expected error faulting AppService config in production mode.");
+            }
+            catch (DataApiBuilderException ex)
+            {
+                Assert.IsTrue(expectError, message: ex.Message);
+                Assert.AreEqual(AppServiceAuthenticationInfo.APPSERVICE_PROD_MISSING_ENV_CONFIG, ex.Message);
+            }
+        }
+
         /// <summary>
         /// Integration test that validates schema introspection requests fail
         /// when allow-introspection is false in the runtime configuration.
diff --git a/src/Service/AuthenticationHelpers/AppServiceAuthenticationInformation.cs b/src/Service/AuthenticationHelpers/AppServiceAuthenticationInformation.cs
new file mode 100644
index 0000000000..eb4675a91c
--- /dev/null
+++ b/src/Service/AuthenticationHelpers/AppServiceAuthenticationInformation.cs
@@ -0,0 +1,52 @@
+using System;
+
+namespace Azure.DataApiBuilder.Service.AuthenticationHelpers
+{
+    /// <summary>
+    /// Info about the App Services configuration on the host. This class is an abridged mirror of
+    /// Microsoft.Identity.Web's AppServicesAuthenticationInformation.cs helper class used to
+    /// detect whether the app is running in an Azure App Service environment.
+    /// </summary>
+    /// <seealso cref="https://github.com/AzureAD/microsoft-identity-web/blob/master/src/Microsoft.Identity.Web/AppServicesAuth/AppServicesAuthenticationInformation.cs"/>
+    public static class AppServiceAuthenticationInfo
+    {
+        /// <summary>
+        /// Environment variable key whose value represents whether AppService EasyAuth is enabled ("true" or "false").
+        /// </summary>
+        public const string APPSERVICESAUTH_ENABLED_ENVVAR = "WEBSITE_AUTH_ENABLED";
+        /// <summary>
+        /// Environment variable key whose value represents Identity Provider such as "AzureActiveDirectory"
+        /// </summary>
+        public const string APPSERVICESAUTH_IDENTITYPROVIDER_ENVVAR = "WEBSITE_AUTH_DEFAULT_PROVIDER";
+        /// <summary>
+        /// Error message used when AppService Authentication is configured in production mode in a non AppService Environment.
+        /// </summary>
+        public const string APPSERVICE_PROD_MISSING_ENV_CONFIG = "AppService environment not detected while runtime is in production mode.";
+        /// <summary>
+        /// Warning message logged when AppService environment not detected (applicable to development mode).
+        /// </summary>
+        public const string APPSERVICE_DEV_MISSING_ENV_CONFIG = "AppService environment not detected, EasyAuth authentication may not behave as expected.";
+
+        /// <summary>
+        /// Returns a best guess whether AppService is enabled in the environment by checking for
+        /// existence and value population of known AppService environment variables.
+        /// This check is determined to be "best guess" because environment variables could be
+        /// manually added or overridden.
+        /// This check's purpose is to help warn developers that an AppService environment is not detected
+        /// where the DataApiBuilder service is executing and DataApiBuilder is configured to use AppService
+        /// as the identity provider.
+        /// </summary>
+        public static bool AreExpectedAppServiceEnvVarsPresent()
+        {
+            string? appServiceEnabled = Environment.GetEnvironmentVariable(APPSERVICESAUTH_ENABLED_ENVVAR);
+            string? appServiceIdentityProvider = Environment.GetEnvironmentVariable(APPSERVICESAUTH_IDENTITYPROVIDER_ENVVAR);
+
+            if (string.IsNullOrEmpty(appServiceEnabled) || string.IsNullOrEmpty(appServiceIdentityProvider))
+            {
+                return false;
+            }
+
+            return appServiceEnabled.Equals(value: "true", comparisonType: StringComparison.OrdinalIgnoreCase);
+        }
+    }
+}
diff --git a/src/Service/AuthenticationHelpers/EasyAuthAuthenticationDefaults.cs b/src/Service/AuthenticationHelpers/EasyAuthAuthenticationDefaults.cs
index acf036e248..4d6cc322ae 100644
--- a/src/Service/AuthenticationHelpers/EasyAuthAuthenticationDefaults.cs
+++ b/src/Service/AuthenticationHelpers/EasyAuthAuthenticationDefaults.cs
@@ -1,12 +1,12 @@
 namespace Azure.DataApiBuilder.Service.AuthenticationHelpers
 {
     /// <summary>
-    /// Default values related to StaticWebAppAuthentication handler.
+    /// Default values related to EasyAuthAuthentication handler.
     /// </summary>
     public static class EasyAuthAuthenticationDefaults
     {
         /// <summary>
-        /// The default value used for StaticWebAppAuthenticationOptions.AuthenticationScheme.
+        /// The default value used for EasyAuthAuthenticationOptions.AuthenticationScheme.
         /// </summary>
         public const string AUTHENTICATIONSCHEME = "EasyAuthAuthentication";
 
diff --git a/src/Service/Startup.cs b/src/Service/Startup.cs
index 5ea8f012f3..272c06c67d 100644
--- a/src/Service/Startup.cs
+++ b/src/Service/Startup.cs
@@ -383,7 +383,7 @@ public void Configure(IApplicationBuilder app, IWebHostEnvironment env, RuntimeC
         /// </summary>
         /// <param name="services">The service collection where authentication services are added.</param>
         /// <param name="runtimeConfigurationProvider">The provider used to load runtime configuration.</param>
-        private static void ConfigureAuthentication(IServiceCollection services, RuntimeConfigProvider runtimeConfigurationProvider)
+        private void ConfigureAuthentication(IServiceCollection services, RuntimeConfigProvider runtimeConfigurationProvider)
         {
             if (runtimeConfigurationProvider.TryGetRuntimeConfiguration(out RuntimeConfig? runtimeConfig) && runtimeConfig.AuthNConfig != null)
             {
@@ -404,11 +404,27 @@ private static void ConfigureAuthentication(IServiceCollection services, Runtime
                 }
                 else if (runtimeConfig.IsEasyAuthAuthenticationProvider())
                 {
+                    EasyAuthType easyAuthType = (EasyAuthType)Enum.Parse(typeof(EasyAuthType), runtimeConfig.AuthNConfig.Provider, ignoreCase: true);
+                    bool isProductionMode = !runtimeConfigurationProvider.IsDeveloperMode();
+                    bool appServiceEnvironmentDetected = AppServiceAuthenticationInfo.AreExpectedAppServiceEnvVarsPresent();
+
+                    if (easyAuthType == EasyAuthType.AppService && !appServiceEnvironmentDetected)
+                    {
+                        if (isProductionMode)
+                        {
+                            throw new DataApiBuilderException(
+                                message: AppServiceAuthenticationInfo.APPSERVICE_PROD_MISSING_ENV_CONFIG,
+                                statusCode: System.Net.HttpStatusCode.ServiceUnavailable,
+                                subStatusCode: DataApiBuilderException.SubStatusCodes.ErrorInInitialization);
+                        }
+                        else
+                        {
+                            _logger.LogWarning(AppServiceAuthenticationInfo.APPSERVICE_DEV_MISSING_ENV_CONFIG);
+                        }
+                    }
+
                     services.AddAuthentication(EasyAuthAuthenticationDefaults.AUTHENTICATIONSCHEME)
-                        .AddEasyAuthAuthentication(
-                            (EasyAuthType)Enum.Parse(typeof(EasyAuthType),
-                                runtimeConfig.AuthNConfig.Provider,
-                                ignoreCase: true));
+                        .AddEasyAuthAuthentication(easyAuthAuthenticationProvider: easyAuthType);
                 }
                 else if (runtimeConfigurationProvider.IsDeveloperMode() && runtimeConfig.IsAuthenticationSimulatorEnabled())
                 {