diff --git a/release_notes.md b/release_notes.md
index aa232c219..7333dc06a 100644
--- a/release_notes.md
+++ b/release_notes.md
@@ -4,6 +4,8 @@
 
 ### New Features
 
+- Fail fast if extendedSessionsEnabled set to 'true' for the worker type that doesn't support extended sessions (https://github.com/Azure/azure-functions-durable-extension/pull/2732).
+
 ### Bug Fixes
 
 - Fix custom connection name not working when using IDurableClientFactory.CreateClient() - contributed by [@hctan](https://github.com/hctan)
diff --git a/src/WebJobs.Extensions.DurableTask/DurableTaskExtension.cs b/src/WebJobs.Extensions.DurableTask/DurableTaskExtension.cs
index 937b236ea..4e59f460c 100644
--- a/src/WebJobs.Extensions.DurableTask/DurableTaskExtension.cs
+++ b/src/WebJobs.Extensions.DurableTask/DurableTaskExtension.cs
@@ -359,7 +359,7 @@ void IExtensionConfigProvider.Initialize(ExtensionConfigContext context)
             }
 
             // Throw if any of the configured options are invalid
-            this.Options.Validate(this.nameResolver, this.TraceHelper);
+            this.Options.Validate(this.nameResolver);
 
 #pragma warning disable CS0618 // Type or member is obsolete
 
diff --git a/src/WebJobs.Extensions.DurableTask/Options/DurableTaskOptions.cs b/src/WebJobs.Extensions.DurableTask/Options/DurableTaskOptions.cs
index bc555386f..c7322044e 100644
--- a/src/WebJobs.Extensions.DurableTask/Options/DurableTaskOptions.cs
+++ b/src/WebJobs.Extensions.DurableTask/Options/DurableTaskOptions.cs
@@ -302,7 +302,7 @@ internal void TraceConfiguration(EndToEndTraceHelper traceHelper, JObject storag
             traceHelper.TraceConfiguration(this.HubName, configurationJson.ToString(Formatting.None));
         }
 
-        internal void Validate(INameResolver environmentVariableResolver, EndToEndTraceHelper traceHelper)
+        internal void Validate(INameResolver environmentVariableResolver)
         {
             if (string.IsNullOrEmpty(this.HubName))
             {
@@ -320,12 +320,9 @@ internal void Validate(INameResolver environmentVariableResolver, EndToEndTraceH
                 runtimeLanguage != null && // If we don't know from the environment variable, don't assume customer isn't .NET
                 !string.Equals(runtimeLanguage, "dotnet", StringComparison.OrdinalIgnoreCase))
             {
-                traceHelper.ExtensionWarningEvent(
-                    hubName: this.HubName,
-                    functionName: string.Empty,
-                    instanceId: string.Empty,
-                    message: "Durable Functions does not work with extendedSessions = true for non-.NET languages. This value is being set to false instead. See https://docs.microsoft.com/en-us/azure/azure-functions/durable/durable-functions-perf-and-scale#extended-sessions for more details.");
-                this.ExtendedSessionsEnabled = false;
+                throw new InvalidOperationException(
+                    "Durable Functions with extendedSessionsEnabled set to 'true' is only supported when using the in-process .NET worker. Please remove the setting or change it to 'false'." +
+                    "See https://docs.microsoft.com/azure/azure-functions/durable/durable-functions-perf-and-scale#extended-sessions for more details.");
             }
 
             this.Notifications.Validate();
diff --git a/test/Common/DurableTaskEndToEndTests.cs b/test/Common/DurableTaskEndToEndTests.cs
index 489379cdd..0ba61d7f3 100644
--- a/test/Common/DurableTaskEndToEndTests.cs
+++ b/test/Common/DurableTaskEndToEndTests.cs
@@ -5592,16 +5592,24 @@ public async Task ExtendedSessions_OutOfProc_SetToFalse()
                 { "FUNCTIONS_WORKER_RUNTIME", "node" },
             });
 
-            using (var host = TestHelpers.GetJobHostWithOptions(
-                this.loggerProvider,
-                durableTaskOptions,
-                nameResolver: nameResolver))
-            {
-                await host.StartAsync();
-                await host.StopAsync();
-            }
+            InvalidOperationException exception =
+                await Assert.ThrowsAsync<InvalidOperationException>(async () =>
+                {
+                    using (var host = TestHelpers.GetJobHostWithOptions(
+                        this.loggerProvider,
+                        durableTaskOptions,
+                        nameResolver: nameResolver))
+                    {
+                        await host.StartAsync();
+                        await host.StopAsync();
+                    }
+                });
 
-            Assert.False(durableTaskOptions.ExtendedSessionsEnabled);
+            Assert.NotNull(exception);
+            Assert.StartsWith(
+                "Durable Functions with extendedSessionsEnabled set to 'true' is only supported when using",
+                exception.Message,
+                StringComparison.OrdinalIgnoreCase);
         }
 
         [Fact]
diff --git a/test/SmokeTests/e2e-test.ps1 b/test/SmokeTests/e2e-test.ps1
index 5eee1e0fd..ab918da8e 100644
--- a/test/SmokeTests/e2e-test.ps1
+++ b/test/SmokeTests/e2e-test.ps1
@@ -31,7 +31,7 @@ $AzuriteVersion = "3.32.0"
 if ($NoSetup -eq $false) {
 	# Build the docker image first, since that's the most critical step
 	Write-Host "Building sample app Docker container from '$DockerfilePath'..." -ForegroundColor Yellow
-	docker build -f $DockerfilePath -t $ImageName --progress plain $PSScriptRoot/../../
+	docker build --pull -f $DockerfilePath -t $ImageName --progress plain $PSScriptRoot/../../
 	Exit-OnError
 
 	# Next, download and start the Azurite emulator Docker image
@@ -58,6 +58,16 @@ if ($NoSetup -eq $false) {
 		Start-Sleep -Seconds 30  # Adjust the sleep duration based on your SQL Server container startup time
 		Exit-OnError
 
+		Write-Host "Checking if SQL Server is still running..." -ForegroundColor Yellow
+		$sqlServerStatus = docker inspect -f '{{.State.Status}}' mssql-server
+		Exit-OnError
+
+		if ($sqlServerStatus -ne "running") {
+			Write-Host "Unexpected SQL Server status: $sqlServerStatus" -ForegroundColor Yellow
+			docker logs mssql-server
+			exit 1;
+		}
+
  		# Get SQL Server IP Address - used to create SQLDB_Connection
 		Write-Host "Getting IP Address..." -ForegroundColor Yellow
 	 	$serverIpAddress = docker inspect -f '{{range .NetworkSettings.Networks}}{{.IPAddress}}{{end}}' mssql-server