diff --git a/lib/Controller/ChattyLLMController.php b/lib/Controller/ChattyLLMController.php
index 3d4c337a..0772d325 100644
--- a/lib/Controller/ChattyLLMController.php
+++ b/lib/Controller/ChattyLLMController.php
@@ -550,7 +550,7 @@ public function regenerateForSession(int $sessionId, int $messageId): JSONRespon
 	 *
 	 * @param int $taskId The message generation task ID
 	 * @param int $sessionId The chat session ID
-	 * @return JSONResponse<Http::STATUS_OK, AssistantChatAgencyMessage, array{}>|JSONResponse<Http::STATUS_EXPECTATION_FAILED, array{task_status: int, slow_pickup: bool, task_output?: array<string, list<numeric|string>|numeric|string>|null}, array{}>|JSONResponse<Http::STATUS_INTERNAL_SERVER_ERROR|Http::STATUS_UNAUTHORIZED|Http::STATUS_BAD_REQUEST|Http::STATUS_NOT_FOUND, array{error: string}, array{}>
+	 * @return JSONResponse<Http::STATUS_OK, AssistantChatAgencyMessage, array{}>|JSONResponse<Http::STATUS_EXPECTATION_FAILED, array{task_status: int, slow_pickup: bool, task_output?: array<string, list<numeric|string>|numeric|string>|null}, array{}>|JSONResponse<Http::STATUS_BAD_REQUEST, array{error: string, task_status?: int, userFacingErrorMessage?: ?string}, array{}>|JSONResponse<Http::STATUS_INTERNAL_SERVER_ERROR|Http::STATUS_UNAUTHORIZED|Http::STATUS_NOT_FOUND, array{error: string}, array{}>
 	 * @throws MultipleObjectsReturnedException
 	 * @throws \OCP\DB\Exception
 	 *
@@ -610,7 +610,11 @@ public function checkMessageGenerationTask(int $taskId, int $sessionId): JSONRes
 			}
 			return new JSONResponse($responsePayload, Http::STATUS_EXPECTATION_FAILED);
 		} elseif ($task->getstatus() === Task::STATUS_FAILED || $task->getstatus() === Task::STATUS_CANCELLED) {
-			return new JSONResponse(['error' => 'task_failed_or_canceled', 'task_status' => $task->getstatus()], Http::STATUS_BAD_REQUEST);
+			return new JSONResponse([
+				'error' => 'task_failed_or_canceled',
+				'task_status' => $task->getstatus(),
+				'userFacingErrorMessage' => $task->getUserFacingErrorMessage(),
+			], Http::STATUS_BAD_REQUEST);
 		}
 		return new JSONResponse(['error' => 'unknown_error', 'task_status' => $task->getstatus()], Http::STATUS_BAD_REQUEST);
 	}
diff --git a/openapi.json b/openapi.json
index 37de5735..2bc9573a 100644
--- a/openapi.json
+++ b/openapi.json
@@ -5052,6 +5052,32 @@
                             }
                         }
                     },
+                    "400": {
+                        "description": "Task processing failed",
+                        "content": {
+                            "application/json": {
+                                "schema": {
+                                    "type": "object",
+                                    "required": [
+                                        "error"
+                                    ],
+                                    "properties": {
+                                        "error": {
+                                            "type": "string"
+                                        },
+                                        "task_status": {
+                                            "type": "integer",
+                                            "format": "int64"
+                                        },
+                                        "userFacingErrorMessage": {
+                                            "type": "string",
+                                            "nullable": true
+                                        }
+                                    }
+                                }
+                            }
+                        }
+                    },
                     "500": {
                         "description": "",
                         "content": {
@@ -5118,24 +5144,6 @@
                             }
                         }
                     },
-                    "400": {
-                        "description": "Task processing failed",
-                        "content": {
-                            "application/json": {
-                                "schema": {
-                                    "type": "object",
-                                    "required": [
-                                        "error"
-                                    ],
-                                    "properties": {
-                                        "error": {
-                                            "type": "string"
-                                        }
-                                    }
-                                }
-                            }
-                        }
-                    },
                     "404": {
                         "description": "Session was not found",
                         "content": {
diff --git a/src/components/ChattyLLM/ChattyLLMInputForm.vue b/src/components/ChattyLLM/ChattyLLMInputForm.vue
index da2b310c..51cda77f 100644
--- a/src/components/ChattyLLM/ChattyLLMInputForm.vue
+++ b/src/components/ChattyLLM/ChattyLLMInputForm.vue
@@ -529,7 +529,7 @@ export default {
 						}
 					} catch (error) {
 						console.error('checkGenerationTask error:', error)
-						showError(t('assistant', 'Error generating a response'))
+						showError(error?.response?.data?.userFacingErrorMessage ?? t('assistant', 'Error generating a response'))
 					}
 					this.streamingMessage = null
 					this.userScrolled = false
@@ -945,7 +945,7 @@ export default {
 				}
 			} catch (error) {
 				console.error('scheduleGenerationTask error:', error)
-				showError(t('assistant', 'Error generating a response'))
+				showError(error?.response?.data?.userFacingErrorMessage ?? t('assistant', 'Error generating a response'))
 			} finally {
 				this.loading.llmGeneration = false
 				this.loading.llmRunning = false
@@ -973,7 +973,7 @@ export default {
 				}
 			} catch (error) {
 				console.error('scheduleRegenerationTask error:', error)
-				showError(t('assistant', 'Error regenerating a response'))
+				showError(error?.response?.data?.userFacingErrorMessage ?? t('assistant', 'Error regenerating a response'))
 			} finally {
 				this.loading.llmGeneration = false
 				this.loading.llmRunning = false
@@ -1052,7 +1052,7 @@ export default {
 						if (error.response?.status !== 417) {
 							console.error('checkTaskPolling error', error)
 							clearInterval(this.pollMessageGenerationTimerId)
-							reject(new Error('Message generation task check failed'))
+							reject(error)
 						} else {
 							console.debug('checkTaskPolling, task is still scheduled or running')
 							this.slowPickup = error.response.data.slow_pickup