diff --git a/.changes/next-release/bugfix-9834036d-17d5-4064-86da-8769b80dfa9b.json b/.changes/next-release/bugfix-9834036d-17d5-4064-86da-8769b80dfa9b.json
new file mode 100644
index 00000000000..7038fd8c87c
--- /dev/null
+++ b/.changes/next-release/bugfix-9834036d-17d5-4064-86da-8769b80dfa9b.json
@@ -0,0 +1,4 @@
+{
+  "type" : "bugfix",
+  "description" : "Amazon Q /doc: Prompt users to start a new documentation task if current task failed"
+}
\ No newline at end of file
diff --git a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqDoc/controller/DocController.kt b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqDoc/controller/DocController.kt
index c52bedf1d96..8e16053619e 100644
--- a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqDoc/controller/DocController.kt
+++ b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqDoc/controller/DocController.kt
@@ -407,10 +407,9 @@ class DocController(
 
             else -> {
                 logger.error { "$FEATURE_NAME: OpenDiff event is received for a conversation that has ${session.sessionState.phase} phase" }
-                messenger.sendError(
+                messenger.sendErrorToUser(
                     tabId = message.tabId,
                     errMessage = message("amazonqFeatureDev.exception.open_diff_failed"),
-                    retries = 0,
                     conversationId = session.conversationIdUnsafe
                 )
             }
@@ -509,10 +508,9 @@ class DocController(
             )
         } catch (err: Exception) {
             val message = createUserFacingErrorMessage("Failed to insert code changes: ${err.message}")
-            messenger.sendError(
+            messenger.sendErrorToUser(
                 tabId = tabId,
                 errMessage = message ?: message("amazonqFeatureDev.exception.insert_code_failed"),
-                retries = retriesRemaining(session),
                 conversationId = session?.conversationIdUnsafe
             )
         }
@@ -590,10 +588,9 @@ class DocController(
 
         when (err) {
             is RepoSizeError -> {
-                messenger.sendError(
+                messenger.sendErrorToUser(
                     tabId = tabId,
                     errMessage = err.message,
-                    retries = retriesRemaining(session),
                     conversationId = session?.conversationIdUnsafe
                 )
                 messenger.sendSystemPrompt(
@@ -609,10 +606,9 @@ class DocController(
             }
 
             is ZipFileError -> {
-                messenger.sendError(
+                messenger.sendErrorToUser(
                     tabId = tabId,
                     errMessage = err.message,
-                    retries = 0,
                     conversationId = session?.conversationIdUnsafe
                 )
             }
@@ -704,10 +700,9 @@ class DocController(
                     else -> message("amazonqFeatureDev.error_text")
                 }
 
-                messenger.sendError(
+                messenger.sendErrorToUser(
                     tabId = tabId,
                     errMessage = defaultMessage,
-                    retries = retriesRemaining(session),
                     conversationId = session?.conversationIdUnsafe
                 )
             }
@@ -805,9 +800,12 @@ class DocController(
             ) {
                 return
             }
-
             if (filePaths.isEmpty() && deletedFiles.isEmpty()) {
-                handleEmptyFiles(followUpMessage, session)
+                messenger.sendErrorToUser(
+                    followUpMessage.tabId,
+                    message("amazonqDoc.error.generating"),
+                    conversationId = session.conversationId
+                )
                 return
             }
 
@@ -862,37 +860,6 @@ class DocController(
         }
     }
 
-    private suspend fun handleEmptyFiles(
-        message: IncomingDocMessage.FollowupClicked,
-        session: DocSession,
-    ) {
-        messenger.sendAnswer(
-            message = message("amazonqDoc.error.generating"),
-            messageType = DocMessageType.Answer,
-            tabId = message.tabId,
-            canBeVoted = true
-        )
-
-        messenger.sendAnswer(
-            messageType = DocMessageType.SystemPrompt,
-            tabId = message.tabId,
-            followUp = if (retriesRemaining(session) > 0) {
-                listOf(
-                    FollowUp(
-                        pillText = message("amazonqFeatureDev.follow_up.retry"),
-                        type = FollowUpTypes.RETRY,
-                        status = FollowUpStatusType.Warning
-                    )
-                )
-            } else {
-                emptyList()
-            }
-        )
-
-        // Lock the chat input until they explicitly click retry
-        messenger.sendChatInputEnabledMessage(tabId = message.tabId, enabled = false)
-    }
-
     private suspend fun retryRequests(tabId: String) {
         var session: DocSession? = null
         docGenerationTask = DocGenerationTask()
diff --git a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqDoc/controller/DocControllerExtensions.kt b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqDoc/controller/DocControllerExtensions.kt
index f16503e2c02..583b1f3d984 100644
--- a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqDoc/controller/DocControllerExtensions.kt
+++ b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqDoc/controller/DocControllerExtensions.kt
@@ -6,13 +6,11 @@ package software.aws.toolkits.jetbrains.services.amazonqDoc.controller
 import com.intellij.notification.NotificationAction
 import software.aws.toolkits.jetbrains.services.amazonqDoc.inProgress
 import software.aws.toolkits.jetbrains.services.amazonqDoc.messages.DocMessageType
-import software.aws.toolkits.jetbrains.services.amazonqDoc.messages.FollowUp
-import software.aws.toolkits.jetbrains.services.amazonqDoc.messages.FollowUpStatusType
-import software.aws.toolkits.jetbrains.services.amazonqDoc.messages.FollowUpTypes
 import software.aws.toolkits.jetbrains.services.amazonqDoc.messages.sendAnswer
 import software.aws.toolkits.jetbrains.services.amazonqDoc.messages.sendAsyncEventProgress
 import software.aws.toolkits.jetbrains.services.amazonqDoc.messages.sendChatInputEnabledMessage
 import software.aws.toolkits.jetbrains.services.amazonqDoc.messages.sendCodeResult
+import software.aws.toolkits.jetbrains.services.amazonqDoc.messages.sendErrorToUser
 import software.aws.toolkits.jetbrains.services.amazonqDoc.messages.sendSystemPrompt
 import software.aws.toolkits.jetbrains.services.amazonqDoc.messages.sendUpdatePlaceholder
 import software.aws.toolkits.jetbrains.services.amazonqDoc.messages.sendUpdatePromptProgress
@@ -73,26 +71,12 @@ suspend fun DocController.onCodeGeneration(session: DocSession, message: String,
 
         // Atm this is the only possible path as codegen is mocked to return empty.
         if (filePaths.size or deletedFiles.size == 0) {
-            messenger.sendAnswer(
-                tabId = tabId,
-                messageType = DocMessageType.Answer,
-                message = message("amazonqFeatureDev.code_generation.no_file_changes")
-            )
-            messenger.sendSystemPrompt(
-                tabId = tabId,
-                followUp = if (retriesRemaining(session) > 0) {
-                    listOf(
-                        FollowUp(
-                            pillText = message("amazonqFeatureDev.follow_up.retry"),
-                            type = FollowUpTypes.RETRY,
-                            status = FollowUpStatusType.Warning
-                        )
-                    )
-                } else {
-                    emptyList()
-                }
+            messenger.sendErrorToUser(
+                tabId,
+                message("amazonqDoc.error.generating"),
+                conversationId = session.conversationId
             )
-            messenger.sendChatInputEnabledMessage(tabId = tabId, enabled = false) // Lock chat input until retry is clicked.
+
             return
         }