diff --git a/PluginsAndFeatures/azure-toolkit-for-rider/CHANGELOG.md b/PluginsAndFeatures/azure-toolkit-for-rider/CHANGELOG.md
index 7af0f6ff17..5acc3bd787 100644
--- a/PluginsAndFeatures/azure-toolkit-for-rider/CHANGELOG.md
+++ b/PluginsAndFeatures/azure-toolkit-for-rider/CHANGELOG.md
@@ -7,6 +7,7 @@
 ### Fixed
 
 - Allow comments in the local.settings.json file ([#900](https://github.com/JetBrains/azure-tools-for-intellij/issues/900))
+- Show a more accurate description of errors if the deployment fails ([RIDER-113475](https://youtrack.jetbrains.com/issue/RIDER-113475))
 
 ## [4.2.1] - 2024-10-04
 
diff --git a/PluginsAndFeatures/azure-toolkit-for-rider/azure-intellij-plugin-appservice-dotnet/src/main/kotlin/com/microsoft/azure/toolkit/intellij/appservice/DotNetAppServiceDeployer.kt b/PluginsAndFeatures/azure-toolkit-for-rider/azure-intellij-plugin-appservice-dotnet/src/main/kotlin/com/microsoft/azure/toolkit/intellij/appservice/DotNetAppServiceDeployer.kt
index a2a5ad3a6d..04c012e4e9 100644
--- a/PluginsAndFeatures/azure-toolkit-for-rider/azure-intellij-plugin-appservice-dotnet/src/main/kotlin/com/microsoft/azure/toolkit/intellij/appservice/DotNetAppServiceDeployer.kt
+++ b/PluginsAndFeatures/azure-toolkit-for-rider/azure-intellij-plugin-appservice-dotnet/src/main/kotlin/com/microsoft/azure/toolkit/intellij/appservice/DotNetAppServiceDeployer.kt
@@ -2,9 +2,16 @@
  * Copyright 2018-2024 JetBrains s.r.o. and contributors. Use of this source code is governed by the MIT license.
  */
 
+@file:Suppress("DuplicatedCode")
+
 package com.microsoft.azure.toolkit.intellij.appservice
 
+import com.azure.core.exception.HttpResponseException
 import com.intellij.execution.ExecutionException
+import com.intellij.ide.BrowserUtil
+import com.intellij.notification.Notification
+import com.intellij.notification.NotificationAction
+import com.intellij.notification.NotificationType
 import com.intellij.openapi.components.Service
 import com.intellij.openapi.components.service
 import com.intellij.openapi.diagnostic.logger
@@ -38,6 +45,8 @@ class DotNetAppServiceDeployer(private val project: Project) {
     ): Result<Unit> {
         target.status = AzResource.Status.DEPLOYING
 
+        checkIfTargetIsValid(target)
+
         val publishProjectResult = ArtifactService
             .getInstance(project)
             .publishProjectToFolder(
@@ -72,6 +81,8 @@ class DotNetAppServiceDeployer(private val project: Project) {
     ): Result<Unit> {
         target.status = AzResource.Status.DEPLOYING
 
+        checkIfTargetIsValid(target)
+
         val publishProjectResult = ArtifactService
             .getInstance(project)
             .publishProjectToFolder(
@@ -97,6 +108,24 @@ class DotNetAppServiceDeployer(private val project: Project) {
         )
     }
 
+    private fun checkIfTargetIsValid(target: AppServiceAppBase<*, *, *>) {
+        val appSettings = target.appSettings
+
+        val websiteRunFromPackage = appSettings?.get("WEBSITE_RUN_FROM_PACKAGE")
+        if (websiteRunFromPackage != null && websiteRunFromPackage.startsWith("http")) {
+            Notification(
+                "Azure AppServices",
+                "Invalid application settings",
+                "The WEBSITE_RUN_FROM_PACKAGE environment variable is set to an URL in the application settings. This can prevent successful deployment.",
+                NotificationType.WARNING
+            )
+                .addAction(NotificationAction.createSimple("Open application on the Portal") {
+                    BrowserUtil.open(target.portalUrl)
+                })
+                .notify(project)
+        }
+    }
+
     private fun packageWebAppArtifactDirectory(artifactFolder: File): File? {
         try {
             val zipFile = Files.createTempFile(artifactFolder.nameWithoutExtension, ".zip").toFile()
@@ -134,7 +163,15 @@ class DotNetAppServiceDeployer(private val project: Project) {
         updateStatusText("Starting deployment...")
         updateStatusText("Trying to deploy artifact to ${webAppBase.name()}...")
 
-        webAppBase.zipDeployAsync(zipFile)?.awaitSingleOrNull()
+        try {
+            webAppBase.zipDeployAsync(zipFile)?.awaitSingleOrNull()
+        } catch (e: HttpResponseException) {
+            LOG.warn("Unable to deploy artifact to Azure resource due to the unsuccessful status code", e)
+            return Result.failure(ExecutionException(e.message))
+        } catch (e: Exception) {
+            LOG.warn("Unable to deploy artifact to Azure resource", e)
+            return Result.failure(ExecutionException(e.message))
+        }
 
         updateStatusText("Successfully deployed the artifact to ${webAppBase.defaultHostname()}")
 
diff --git a/PluginsAndFeatures/azure-toolkit-for-rider/azure-intellij-plugin-lib-dotnet/src/main/kotlin/com/microsoft/azure/toolkit/intellij/legacy/common/AzureDeploymentState.kt b/PluginsAndFeatures/azure-toolkit-for-rider/azure-intellij-plugin-lib-dotnet/src/main/kotlin/com/microsoft/azure/toolkit/intellij/legacy/common/AzureDeploymentState.kt
index dfa9f615d5..0fa55063be 100644
--- a/PluginsAndFeatures/azure-toolkit-for-rider/azure-intellij-plugin-lib-dotnet/src/main/kotlin/com/microsoft/azure/toolkit/intellij/legacy/common/AzureDeploymentState.kt
+++ b/PluginsAndFeatures/azure-toolkit-for-rider/azure-intellij-plugin-lib-dotnet/src/main/kotlin/com/microsoft/azure/toolkit/intellij/legacy/common/AzureDeploymentState.kt
@@ -39,8 +39,7 @@ abstract class AzureDeploymentState<T>(
         processHandler.startNotify()
         consoleView.attachToProcess(processHandler)
 
-        val processScope = scope.childScope("Azure Deployment scope")
-        processScope.launch(Dispatchers.Default) {
+        val job = scope.launch(Dispatchers.Default) {
             try {
                 val result = executeSteps(processHandler)
                 processHandler.putUserData(RunConfigurationUtils.AZURE_RUN_STATE_RESULT, true)
@@ -49,18 +48,16 @@ abstract class AzureDeploymentState<T>(
             catch (ce: CancellationException) {
                 processHandlerMessenger?.info("Process was cancelled")
                 onFail(ce, processHandler)
-                throw ce
             }
             catch (t: Throwable) {
                 processHandlerMessenger?.error(t)
                 onFail(t, processHandler)
-                throw t
             }
         }
 
         processHandler.addProcessListener(object : ProcessAdapter() {
             override fun processTerminated(event: ProcessEvent) {
-                processScope.cancel()
+                job.cancel()
             }
         })