diff --git a/client/src/components/BackgroundTasks/BackgroundTasksWidget.test.tsx b/client/src/components/BackgroundTasks/BackgroundTasksWidget.test.tsx
new file mode 100644
index 000000000..3883a5f5e
--- /dev/null
+++ b/client/src/components/BackgroundTasks/BackgroundTasksWidget.test.tsx
@@ -0,0 +1,45 @@
+import { describe, it, expect, vi, beforeEach } from 'vitest'
+import { screen } from '@testing-library/react'
+import { render } from '../../../tests/helpers/render'
+import { useBackgroundTasksStore, type BackgroundImportTask } from '../../store/backgroundTasksStore'
+import BackgroundTasksWidget from './BackgroundTasksWidget'
+
+vi.mock('../../api/websocket', () => ({ addListener: vi.fn(), removeListener: vi.fn() }))
+vi.mock('../../api/client', () => ({
+  // Keep the rehydrate/poll backstops pending so the seeded state is what renders.
+  reservationsApi: { importJobStatus: vi.fn(() => new Promise(() => {})) },
+}))
+
+const task = (overrides: Partial<BackgroundImportTask> = {}): BackgroundImportTask => ({
+  id: 'j1',
+  tripId: 't1',
+  label: 'voucher.pdf',
+  status: 'done',
+  done: 0,
+  total: 1,
+  items: [],
+  warnings: [],
+  ...overrides,
+})
+
+beforeEach(() => {
+  vi.clearAllMocks()
+  useBackgroundTasksStore.setState({ tasks: [] })
+})
+
+describe('BackgroundTasksWidget', () => {
+  it('shows the warnings when a finished job produced no items', () => {
+    const warning = 'voucher.pdf: AI parsing failed — LLM request failed (400): response_format unsupported'
+    useBackgroundTasksStore.setState({ tasks: [task({ warnings: [warning] })] })
+    render(<BackgroundTasksWidget />)
+    expect(screen.getByText('No reservations could be extracted from the uploaded files.')).toBeInTheDocument()
+    expect(screen.getByText(warning)).toBeInTheDocument()
+  })
+
+  it('shows only the empty-preview note when there are no warnings', () => {
+    useBackgroundTasksStore.setState({ tasks: [task()] })
+    render(<BackgroundTasksWidget />)
+    expect(screen.getByText('No reservations could be extracted from the uploaded files.')).toBeInTheDocument()
+    expect(screen.queryByText(/AI parsing failed/)).not.toBeInTheDocument()
+  })
+})
diff --git a/client/src/components/BackgroundTasks/BackgroundTasksWidget.tsx b/client/src/components/BackgroundTasks/BackgroundTasksWidget.tsx
index b53a3e57a..977833e4e 100644
--- a/client/src/components/BackgroundTasks/BackgroundTasksWidget.tsx
+++ b/client/src/components/BackgroundTasks/BackgroundTasksWidget.tsx
@@ -136,7 +136,14 @@ export default function BackgroundTasksWidget() {
                   {t('common.import')}
                 </button>
               ) : (
-                <div style={{ fontSize: 'calc(11px * var(--fs-scale-caption, 1))', color: 'var(--text-faint)', marginTop: 1 }}>{t('reservations.import.previewEmpty')}</div>
+                <div style={{ fontSize: 'calc(11px * var(--fs-scale-caption, 1))', color: 'var(--text-faint)', marginTop: 1 }}>
+                  {t('reservations.import.previewEmpty')}
+                  {(task.warnings?.length ?? 0) > 0 && (
+                    <div style={{ color: '#b45309', marginTop: 3, whiteSpace: 'pre-wrap', wordBreak: 'break-word', maxHeight: 96, overflowY: 'auto' }}>
+                      {task.warnings!.join('\n')}
+                    </div>
+                  )}
+                </div>
               )
             )}
 
diff --git a/server/src/nest/llm-parse/clients/openai-compatible.client.ts b/server/src/nest/llm-parse/clients/openai-compatible.client.ts
index 31ea8820a..c3352deec 100644
--- a/server/src/nest/llm-parse/clients/openai-compatible.client.ts
+++ b/server/src/nest/llm-parse/clients/openai-compatible.client.ts
@@ -18,6 +18,10 @@ const MAX_TOKENS = 4096;
  * template inlined in a single user message, no system prompt and no
  * `response_format` (see ./nuextract.ts) — that's how the fine-tune expects to
  * be driven; the generic instruct path applies to every other model.
+ *
+ * Structured output is requested as `json_schema` first; servers that only
+ * support `json_object` (DeepSeek, Mistral, some vLLM/llama.cpp) reject that
+ * with a 400, so the request is retried once in `json_object` mode.
  */
 export class OpenAiCompatibleClient implements LlmExtractionClient {
   async extract(input: LlmExtractionInput): Promise<Record<string, unknown>[]> {
@@ -39,7 +43,7 @@ export class OpenAiCompatibleClient implements LlmExtractionClient {
       });
     }
 
-    const body = {
+    const baseBody = {
       model: input.model,
       max_tokens: MAX_TOKENS,
       // Extraction is a deterministic task — Ollama defaults to 0.7, which makes
@@ -53,33 +57,24 @@ export class OpenAiCompatibleClient implements LlmExtractionClient {
             { role: 'system', content: input.prompt },
             { role: 'user', content: userContent },
           ],
-      ...(nuextract
-        ? {}
-        : {
-            response_format: {
-              type: 'json_schema' as const,
-              json_schema: { name: 'reservations', schema: input.jsonSchema, strict: false },
-            },
-          }),
     };
+    const body = nuextract
+      ? baseBody
+      : {
+          ...baseBody,
+          response_format: {
+            type: 'json_schema' as const,
+            json_schema: { name: 'reservations', schema: input.jsonSchema, strict: false },
+          },
+        };
 
-    const controller = new AbortController();
-    const timer = setTimeout(() => controller.abort(), TIMEOUT_MS);
-    let res: Response;
-    try {
-      // baseUrl is user-configurable — guard it against pointing at the cloud
-      // metadata endpoint, while still allowing a local/LAN Ollama.
-      res = await safeFetchLlm(url, {
-        method: 'POST',
-        signal: controller.signal,
-        headers: {
-          'content-type': 'application/json',
-          ...(input.apiKey ? { authorization: `Bearer ${input.apiKey}` } : {}),
-        },
-        body: JSON.stringify(body),
-      });
-    } finally {
-      clearTimeout(timer);
+    let res = await this.send(url, body, input.apiKey);
+    // Servers that only support `json_object` (DeepSeek, Mistral, some
+    // vLLM/llama.cpp) reject `json_schema` with a 400 — retry once in
+    // `json_object` mode. The system prompt already dictates the exact output
+    // shape (and mentions JSON, which json_object mode requires).
+    if (!res.ok && res.status === 400 && !nuextract) {
+      res = await this.send(url, { ...baseBody, response_format: { type: 'json_object' as const } }, input.apiKey);
     }
 
     if (!res.ok) {
@@ -93,6 +88,26 @@ export class OpenAiCompatibleClient implements LlmExtractionClient {
     const content = data.choices?.[0]?.message?.content;
     return nuextract ? parseNuExtract(content) : parseReservations(content);
   }
+
+  private async send(url: string, body: unknown, apiKey?: string): Promise<Response> {
+    const controller = new AbortController();
+    const timer = setTimeout(() => controller.abort(), TIMEOUT_MS);
+    try {
+      // baseUrl is user-configurable — guard it against pointing at the cloud
+      // metadata endpoint, while still allowing a local/LAN Ollama.
+      return await safeFetchLlm(url, {
+        method: 'POST',
+        signal: controller.signal,
+        headers: {
+          'content-type': 'application/json',
+          ...(apiKey ? { authorization: `Bearer ${apiKey}` } : {}),
+        },
+        body: JSON.stringify(body),
+      });
+    } finally {
+      clearTimeout(timer);
+    }
+  }
 }
 
 /** Strip code fences and JSON.parse; `null` on failure. */
diff --git a/server/src/nest/llm-parse/llm-parse.service.ts b/server/src/nest/llm-parse/llm-parse.service.ts
index 322ea08be..e2b7ce6ae 100644
--- a/server/src/nest/llm-parse/llm-parse.service.ts
+++ b/server/src/nest/llm-parse/llm-parse.service.ts
@@ -71,6 +71,7 @@ export class LlmParseService {
         }
       }
     } catch (err) {
+      console.error(`[llm-parse] Could not read "${file.originalName}":`, err instanceof Error ? err.message : err);
       return {
         kiItems: [],
         warnings: [`${file.originalName}: could not read file — ${err instanceof Error ? err.message : String(err)}`],
@@ -90,6 +91,7 @@ export class LlmParseService {
         });
         return { kiItems: routed.kiItems, warnings: [...warnings, ...routed.warnings] };
       } catch (err) {
+        console.error(`[llm-parse] AI parsing failed for "${file.originalName}" (provider=${config.provider}):`, err instanceof Error ? err.message : err);
         return {
           kiItems: [],
           warnings: [`${file.originalName}: AI parsing failed — ${err instanceof Error ? err.message : String(err)}`],
@@ -102,6 +104,7 @@ export class LlmParseService {
       raw = await createLlmClient(config).extract(input);
       console.debug('[DEBUG] Raw LLM Response: ', raw);
     } catch (err) {
+      console.error(`[llm-parse] AI parsing failed for "${file.originalName}" (provider=${config.provider}):`, err instanceof Error ? err.message : err);
       return {
         kiItems: [],
         warnings: [`${file.originalName}: AI parsing failed — ${err instanceof Error ? err.message : String(err)}`],
diff --git a/server/tests/unit/nest/llm-parse/clients.test.ts b/server/tests/unit/nest/llm-parse/clients.test.ts
index 961905a37..78562b2a2 100644
--- a/server/tests/unit/nest/llm-parse/clients.test.ts
+++ b/server/tests/unit/nest/llm-parse/clients.test.ts
@@ -55,6 +55,41 @@ describe('OpenAiCompatibleClient', () => {
   it('throws on non-2xx', async () => {
     mockFetch(() => jsonResponse({ error: 'bad' }, false, 401));
     await expect(new OpenAiCompatibleClient().extract(baseInput)).rejects.toThrow(/401/);
+    expect(safeFetchLlmMock).toHaveBeenCalledTimes(1); // no retry on non-400
+  });
+
+  it('retries once with json_object when the server rejects json_schema (400)', async () => {
+    safeFetchLlmMock
+      .mockResolvedValueOnce(jsonResponse({ error: { message: 'response_format type is unavailable' } }, false, 400))
+      .mockResolvedValueOnce(
+        jsonResponse({ choices: [{ message: { content: '{"reservations":[{"@type":"FlightReservation"}]}' } }] }),
+      );
+    const out = await new OpenAiCompatibleClient().extract(baseInput);
+    expect(out).toEqual([{ '@type': 'FlightReservation' }]);
+    expect(safeFetchLlmMock).toHaveBeenCalledTimes(2);
+
+    const first = JSON.parse((safeFetchLlmMock.mock.calls[0][1] as RequestInit).body as string);
+    const second = JSON.parse((safeFetchLlmMock.mock.calls[1][1] as RequestInit).body as string);
+    expect(first.response_format.type).toBe('json_schema');
+    expect(second.response_format).toEqual({ type: 'json_object' });
+    expect(second.messages).toEqual(first.messages);
+    expect(second.model).toBe(first.model);
+  });
+
+  it('throws when the json_object retry also fails (400 twice)', async () => {
+    safeFetchLlmMock
+      .mockResolvedValueOnce(jsonResponse({ error: 'no json_schema' }, false, 400))
+      .mockResolvedValueOnce(jsonResponse({ error: 'no json_object either' }, false, 400));
+    await expect(new OpenAiCompatibleClient().extract(baseInput)).rejects.toThrow(/400/);
+    expect(safeFetchLlmMock).toHaveBeenCalledTimes(2);
+  });
+
+  it('does not retry the NuExtract path on 400', async () => {
+    safeFetchLlmMock.mockResolvedValueOnce(jsonResponse({ error: 'bad' }, false, 400));
+    await expect(
+      new OpenAiCompatibleClient().extract({ ...baseInput, model: 'hf.co/numind/NuExtract-2.0-2B-GGUF:latest' }),
+    ).rejects.toThrow(/400/);
+    expect(safeFetchLlmMock).toHaveBeenCalledTimes(1);
   });
 
   it('sends an image natively as image_url but never a file/pdf part', async () => {
diff --git a/server/tests/unit/nest/llm-parse/llm-parse.service.test.ts b/server/tests/unit/nest/llm-parse/llm-parse.service.test.ts
index c96b96fc4..56045320f 100644
--- a/server/tests/unit/nest/llm-parse/llm-parse.service.test.ts
+++ b/server/tests/unit/nest/llm-parse/llm-parse.service.test.ts
@@ -122,6 +122,14 @@ describe('LlmParseService', () => {
     expect(res.warnings[0]).toMatch(/AI parsing failed/i);
   });
 
+  it('logs the swallowed client error to console.error', async () => {
+    const spy = vi.spyOn(console, 'error').mockImplementation(() => {});
+    extract.mockRejectedValue(new Error('boom'));
+    await svc().parse(file('a.txt'), 1);
+    expect(spy).toHaveBeenCalledWith(expect.stringContaining('[llm-parse]'), 'boom');
+    spy.mockRestore();
+  });
+
   it('routes the local provider through the extraction router instead of the single-shot client', async () => {
     resolveLlmConfig.mockReturnValue(cfg({ provider: 'local', baseUrl: 'http://ollama:11434/v1', apiKey: 'k' }));
     extractText.mockResolvedValue('Hotel booking');
@@ -159,6 +167,15 @@ describe('LlmParseService', () => {
     expect(res.warnings[0]).toMatch(/AI parsing failed/i);
   });
 
+  it('logs the swallowed router error to console.error', async () => {
+    const spy = vi.spyOn(console, 'error').mockImplementation(() => {});
+    resolveLlmConfig.mockReturnValue(cfg({ provider: 'local' }));
+    routeExtraction.mockRejectedValue(new Error('ollama down'));
+    await svc().parse(file('a.txt'), 1);
+    expect(spy).toHaveBeenCalledWith(expect.stringContaining('[llm-parse]'), 'ollama down');
+    spy.mockRestore();
+  });
+
   it('warns when the file cannot be read (text extraction throws)', async () => {
     extractText.mockRejectedValue(new Error('corrupt pdf'));
     const res = await svc().parse(file('a.pdf', '%PDF'), 1);