diff --git a/apps/web/src/components/common/dropzone.tsx b/apps/web/src/components/common/dropzone.tsx
index 0ecc0e3d..b82c0c01 100644
--- a/apps/web/src/components/common/dropzone.tsx
+++ b/apps/web/src/components/common/dropzone.tsx
@@ -1,4 +1,4 @@
-import { FileImage, FileUp, Upload } from "lucide-react";
+import { AlertCircle, FileImage, FileUp, Upload } from "lucide-react";
 import { type DragEvent, useCallback, useEffect, useState } from "react";
 import { useTranslation } from "@/contexts/i18n-context";
 import { useUrlImport } from "@/hooks/use-url-import";
@@ -116,11 +116,19 @@ export function Dropzone({
   const checkFile = fileFilter ?? isImageFile;
   const resolvedAccept = expandAccept(accept);
   const [isDragging, setIsDragging] = useState(false);
+  const [error, setError] = useState<string | null>(null);
   const [urlInput, setUrlInput] = useState("");
   const [urlLoading, setUrlLoading] = useState(false);
   const [urlError, setUrlError] = useState<string | null>(null);
   const [showBulkModal, setShowBulkModal] = useState(false);
 
+  useEffect(() => {
+    if (error) {
+      const timer = setTimeout(() => setError(null), 5000);
+      return () => clearTimeout(timer);
+    }
+  }, [error]);
+
   const { importSingleUrl } = useUrlImport();
 
   const handleUrlSubmit = useCallback(async () => {
@@ -154,20 +162,32 @@ export function Dropzone({
       e.preventDefault();
       e.stopPropagation();
       setIsDragging(false);
-      const files = Array.from(e.dataTransfer.files).filter(checkFile);
-      if (files.length > 0) onFiles?.(files);
+      setError(null);
+      const droppedFiles = Array.from(e.dataTransfer.files);
+      const validFiles = droppedFiles.filter(checkFile);
+      if (validFiles.length > 0) {
+        onFiles?.(validFiles);
+      } else if (droppedFiles.length > 0) {
+        setError(acceptDescription || `This tool accepts ${accept || "image files"}`);
+      }
     },
-    [onFiles, checkFile],
+    [onFiles, checkFile, acceptDescription, accept],
   );
 
   const handleClick = () => {
+    setError(null);
     const input = document.createElement("input");
     input.type = "file";
     input.multiple = multiple;
     if (resolvedAccept) input.accept = resolvedAccept;
     input.onchange = (e) => {
-      const files = Array.from((e.target as HTMLInputElement).files || []).filter(checkFile);
-      if (files.length > 0) onFiles?.(files);
+      const picked = Array.from((e.target as HTMLInputElement).files || []);
+      const validFiles = picked.filter(checkFile);
+      if (validFiles.length > 0) {
+        onFiles?.(validFiles);
+      } else if (picked.length > 0) {
+        setError(acceptDescription || `This tool accepts ${accept || "image files"}`);
+      }
     };
     input.click();
   };
@@ -260,6 +280,13 @@ export function Dropzone({
           {acceptDescription ?? t.dropzone.defaultFormats}
         </p>
 
+        {error && (
+          <p className="mt-3 text-sm text-destructive flex items-center gap-1.5">
+            <AlertCircle className="h-4 w-4 shrink-0" />
+            {error}
+          </p>
+        )}
+
         {!compact && onUrlImport && (
           <>
             <div className="flex items-center gap-2 w-full max-w-xs">
diff --git a/apps/web/src/pages/tool-page.tsx b/apps/web/src/pages/tool-page.tsx
index 8f21c9a0..47ff33dd 100644
--- a/apps/web/src/pages/tool-page.tsx
+++ b/apps/web/src/pages/tool-page.tsx
@@ -1,5 +1,6 @@
 import { MODALITIES, PYTHON_SIDECAR_TOOLS, TOOL_BUNDLE_MAP, TOOLS } from "@snapotter/shared";
 import {
+  AlertCircle,
   CheckCircle2,
   ChevronLeft,
   ChevronRight,
@@ -617,10 +618,30 @@ export function ToolPage() {
     // which also match !hasProcessed and would show the canvas instead of the error)
     if (hasFile && !hasProcessed && currentEntry?.status === "failed") {
       return (
-        <div className="flex flex-col items-center justify-center gap-3 h-full text-center px-4">
-          <p className="text-sm text-red-500">
-            {currentEntry.error ?? t.toolPage.processingFailed}
-          </p>
+        <div className="flex-1 flex items-center justify-center p-6">
+          <div className="text-center max-w-sm">
+            <AlertCircle className="mx-auto h-10 w-10 text-destructive mb-3" />
+            <p className="font-medium text-foreground mb-1">
+              {currentEntry.error || t.toolPage.processingFailed}
+            </p>
+            <p className="text-sm text-muted-foreground mb-4">{t.toolPage.settingsSaved}</p>
+            <div className="flex flex-col gap-2">
+              <button
+                type="button"
+                onClick={handleUndo}
+                className="px-4 py-2 rounded-md bg-primary text-primary-foreground text-sm font-medium hover:opacity-90"
+              >
+                {t.toolPage.tryAgain}
+              </button>
+              <button
+                type="button"
+                onClick={startOver}
+                className="px-4 py-2 rounded-md text-sm text-muted-foreground hover:text-foreground"
+              >
+                {t.toolPage.tryDifferentFile}
+              </button>
+            </div>
+          </div>
         </div>
       );
     }
diff --git a/packages/shared/src/i18n/ar.ts b/packages/shared/src/i18n/ar.ts
index 92bc051e..ae38557a 100644
--- a/packages/shared/src/i18n/ar.ts
+++ b/packages/shared/src/i18n/ar.ts
@@ -2453,6 +2453,9 @@ export const ar: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "تم حفظ إعداداتك.",
+    tryAgain: "حاول مرة أخرى",
+    tryDifferentFile: "جرب ملفًا مختلفًا",
   },
   homePage: {
     generatingPreview: "جاري إنشاء المعاينة...",
diff --git a/packages/shared/src/i18n/de.ts b/packages/shared/src/i18n/de.ts
index ecb33845..974306c1 100644
--- a/packages/shared/src/i18n/de.ts
+++ b/packages/shared/src/i18n/de.ts
@@ -2467,6 +2467,9 @@ export const de: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Ihre Einstellungen wurden gespeichert.",
+    tryAgain: "Erneut versuchen",
+    tryDifferentFile: "Andere Datei versuchen",
   },
   homePage: {
     generatingPreview: "Vorschau wird generiert...",
diff --git a/packages/shared/src/i18n/en.ts b/packages/shared/src/i18n/en.ts
index 8bf8b7df..8fc4061b 100644
--- a/packages/shared/src/i18n/en.ts
+++ b/packages/shared/src/i18n/en.ts
@@ -2417,6 +2417,9 @@ export const en = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Your settings are saved.",
+    tryAgain: "Try again",
+    tryDifferentFile: "Try a different file",
   },
   homePage: {
     generatingPreview: "Generating preview...",
diff --git a/packages/shared/src/i18n/es.ts b/packages/shared/src/i18n/es.ts
index cad20c82..5b7551f1 100644
--- a/packages/shared/src/i18n/es.ts
+++ b/packages/shared/src/i18n/es.ts
@@ -2449,6 +2449,9 @@ export const es: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Tu configuracion se ha guardado.",
+    tryAgain: "Reintentar",
+    tryDifferentFile: "Probar con otro archivo",
   },
   homePage: {
     generatingPreview: "Generando vista previa...",
diff --git a/packages/shared/src/i18n/fr.ts b/packages/shared/src/i18n/fr.ts
index d6e61f98..d24a2e80 100644
--- a/packages/shared/src/i18n/fr.ts
+++ b/packages/shared/src/i18n/fr.ts
@@ -2468,6 +2468,9 @@ export const fr: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Vos parametres sont enregistres.",
+    tryAgain: "Reessayer",
+    tryDifferentFile: "Essayer un autre fichier",
   },
   homePage: {
     generatingPreview: "Generation de l'apercu...",
diff --git a/packages/shared/src/i18n/hi.ts b/packages/shared/src/i18n/hi.ts
index f8dfb451..8bc17b44 100644
--- a/packages/shared/src/i18n/hi.ts
+++ b/packages/shared/src/i18n/hi.ts
@@ -2450,6 +2450,9 @@ export const hi: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "आपकी सेटिंग्स सहेज ली गई हैं।",
+    tryAgain: "पुनः प्रयास करें",
+    tryDifferentFile: "एक अलग फ़ाइल आज़माएं",
   },
   homePage: {
     generatingPreview: "प्रीव्यू जनरेट हो रहा है...",
diff --git a/packages/shared/src/i18n/id.ts b/packages/shared/src/i18n/id.ts
index 7a0420bc..f6a6277f 100644
--- a/packages/shared/src/i18n/id.ts
+++ b/packages/shared/src/i18n/id.ts
@@ -2462,6 +2462,9 @@ export const id: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Pengaturan Anda tersimpan.",
+    tryAgain: "Coba lagi",
+    tryDifferentFile: "Coba file lain",
   },
   homePage: {
     generatingPreview: "Membuat pratinjau...",
diff --git a/packages/shared/src/i18n/it.ts b/packages/shared/src/i18n/it.ts
index b3711766..255386fd 100644
--- a/packages/shared/src/i18n/it.ts
+++ b/packages/shared/src/i18n/it.ts
@@ -2461,6 +2461,9 @@ export const it: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Le impostazioni sono state salvate.",
+    tryAgain: "Riprova",
+    tryDifferentFile: "Prova un file diverso",
   },
   homePage: {
     generatingPreview: "Generazione anteprima...",
diff --git a/packages/shared/src/i18n/ja.ts b/packages/shared/src/i18n/ja.ts
index a6dca42a..d491ad51 100644
--- a/packages/shared/src/i18n/ja.ts
+++ b/packages/shared/src/i18n/ja.ts
@@ -2420,6 +2420,9 @@ export const ja: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "設定は保存されています。",
+    tryAgain: "再試行",
+    tryDifferentFile: "別のファイルを試す",
   },
   homePage: {
     generatingPreview: "プレビューを生成中...",
diff --git a/packages/shared/src/i18n/ko.ts b/packages/shared/src/i18n/ko.ts
index e85133ec..21aee091 100644
--- a/packages/shared/src/i18n/ko.ts
+++ b/packages/shared/src/i18n/ko.ts
@@ -2405,6 +2405,9 @@ export const ko: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "설정이 저장되었습니다.",
+    tryAgain: "다시 시도",
+    tryDifferentFile: "다른 파일 시도",
   },
   homePage: {
     generatingPreview: "미리보기 생성 중...",
diff --git a/packages/shared/src/i18n/nl.ts b/packages/shared/src/i18n/nl.ts
index d00f181a..cf516d06 100644
--- a/packages/shared/src/i18n/nl.ts
+++ b/packages/shared/src/i18n/nl.ts
@@ -2464,6 +2464,9 @@ export const nl: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Uw instellingen zijn opgeslagen.",
+    tryAgain: "Opnieuw proberen",
+    tryDifferentFile: "Een ander bestand proberen",
   },
   homePage: {
     generatingPreview: "Preview genereren...",
diff --git a/packages/shared/src/i18n/pl.ts b/packages/shared/src/i18n/pl.ts
index 5c444f6f..1653f20f 100644
--- a/packages/shared/src/i18n/pl.ts
+++ b/packages/shared/src/i18n/pl.ts
@@ -2465,6 +2465,9 @@ export const pl: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Twoje ustawienia zostaly zapisane.",
+    tryAgain: "Sprobuj ponownie",
+    tryDifferentFile: "Sprobuj inny plik",
   },
   homePage: {
     generatingPreview: "Generowanie podglądu...",
diff --git a/packages/shared/src/i18n/pt-BR.ts b/packages/shared/src/i18n/pt-BR.ts
index 2f3f9366..24ea07cc 100644
--- a/packages/shared/src/i18n/pt-BR.ts
+++ b/packages/shared/src/i18n/pt-BR.ts
@@ -2461,6 +2461,9 @@ export const ptBR: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Suas configuracoes foram salvas.",
+    tryAgain: "Tentar novamente",
+    tryDifferentFile: "Tentar outro arquivo",
   },
   homePage: {
     generatingPreview: "Gerando visualizacao...",
diff --git a/packages/shared/src/i18n/ru.ts b/packages/shared/src/i18n/ru.ts
index 9b36ee56..652b3407 100644
--- a/packages/shared/src/i18n/ru.ts
+++ b/packages/shared/src/i18n/ru.ts
@@ -2463,6 +2463,9 @@ export const ru: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Ваши настройки сохранены.",
+    tryAgain: "Попробовать снова",
+    tryDifferentFile: "Попробовать другой файл",
   },
   homePage: {
     generatingPreview: "Генерация предпросмотра...",
diff --git a/packages/shared/src/i18n/sv.ts b/packages/shared/src/i18n/sv.ts
index 6a3fa4ef..4f1b2078 100644
--- a/packages/shared/src/i18n/sv.ts
+++ b/packages/shared/src/i18n/sv.ts
@@ -2460,6 +2460,9 @@ export const sv: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Dina installningar ar sparade.",
+    tryAgain: "Forsok igen",
+    tryDifferentFile: "Prova en annan fil",
   },
   homePage: {
     generatingPreview: "Genererar forhandsvisning...",
diff --git a/packages/shared/src/i18n/th.ts b/packages/shared/src/i18n/th.ts
index 1a3c4cf7..e59755e2 100644
--- a/packages/shared/src/i18n/th.ts
+++ b/packages/shared/src/i18n/th.ts
@@ -2442,6 +2442,9 @@ export const th: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "บันทึกการตั้งค่าของคุณแล้ว",
+    tryAgain: "ลองอีกครั้ง",
+    tryDifferentFile: "ลองไฟล์อื่น",
   },
   homePage: {
     generatingPreview: "กำลังสร้างตัวอย่าง...",
diff --git a/packages/shared/src/i18n/tr.ts b/packages/shared/src/i18n/tr.ts
index 483ab482..f9feb4f3 100644
--- a/packages/shared/src/i18n/tr.ts
+++ b/packages/shared/src/i18n/tr.ts
@@ -2465,6 +2465,9 @@ export const tr: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Ayarlariniz kaydedildi.",
+    tryAgain: "Tekrar dene",
+    tryDifferentFile: "Farkli bir dosya dene",
   },
   homePage: {
     generatingPreview: "Önizleme oluşturuluyor...",
diff --git a/packages/shared/src/i18n/uk.ts b/packages/shared/src/i18n/uk.ts
index fed29ec0..8ca53c59 100644
--- a/packages/shared/src/i18n/uk.ts
+++ b/packages/shared/src/i18n/uk.ts
@@ -2463,6 +2463,9 @@ export const uk: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Ваші налаштування збережено.",
+    tryAgain: "Спробувати знову",
+    tryDifferentFile: "Спробувати інший файл",
   },
   homePage: {
     generatingPreview: "Генерація попереднього перегляду...",
diff --git a/packages/shared/src/i18n/vi.ts b/packages/shared/src/i18n/vi.ts
index 0ceaecef..6eabf0f7 100644
--- a/packages/shared/src/i18n/vi.ts
+++ b/packages/shared/src/i18n/vi.ts
@@ -2462,6 +2462,9 @@ export const vi: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "Cai dat cua ban da duoc luu.",
+    tryAgain: "Thu lai",
+    tryDifferentFile: "Thu tep khac",
   },
   homePage: {
     generatingPreview: "Đang tạo bản xem trước...",
diff --git a/packages/shared/src/i18n/zh-CN.ts b/packages/shared/src/i18n/zh-CN.ts
index 5d8f08b7..199490d9 100644
--- a/packages/shared/src/i18n/zh-CN.ts
+++ b/packages/shared/src/i18n/zh-CN.ts
@@ -2395,6 +2395,9 @@ export const zhCN: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "您的设置已保存。",
+    tryAgain: "重试",
+    tryDifferentFile: "尝试其他文件",
   },
   homePage: {
     generatingPreview: "正在生成预览...",
diff --git a/packages/shared/src/i18n/zh-TW.ts b/packages/shared/src/i18n/zh-TW.ts
index 04135b0f..56bbffb2 100644
--- a/packages/shared/src/i18n/zh-TW.ts
+++ b/packages/shared/src/i18n/zh-TW.ts
@@ -2393,6 +2393,9 @@ export const zhTW: TranslationKeys = {
     saved: "Saved",
     noChange: "no change",
     download: "Download",
+    settingsSaved: "您的設定已儲存。",
+    tryAgain: "重試",
+    tryDifferentFile: "嘗試其他檔案",
   },
   homePage: {
     generatingPreview: "正在產生預覽...",