diff --git a/frontend/editor/src/core/hooks/tools/shared/useToolOperation.ts b/frontend/editor/src/core/hooks/tools/shared/useToolOperation.ts
index fe1ddc7bc7..a341fe6fd7 100644
--- a/frontend/editor/src/core/hooks/tools/shared/useToolOperation.ts
+++ b/frontend/editor/src/core/hooks/tools/shared/useToolOperation.ts
@@ -406,13 +406,19 @@ export const useToolOperation = <TParams>(
 
           actions.setFiles(processedFiles);
 
-          // Generate thumbnails and download URL concurrently
+          // Generate thumbnails and download URL concurrently. The flag has to clear in a
+          // finally: anything thrown here otherwise leaves the spinner up permanently.
           actions.setGeneratingThumbnails(true);
-          const [thumbnails, downloadInfo] = await Promise.all([
-            generateThumbnails(processedFiles),
-            createDownloadInfo(processedFiles, config.operationType),
-          ]);
-          actions.setGeneratingThumbnails(false);
+          let thumbnails: string[];
+          let downloadInfo: { url: string; filename: string };
+          try {
+            [thumbnails, downloadInfo] = await Promise.all([
+              generateThumbnails(processedFiles),
+              createDownloadInfo(processedFiles, config.operationType),
+            ]);
+          } finally {
+            actions.setGeneratingThumbnails(false);
+          }
 
           actions.setThumbnails(thumbnails);
 
diff --git a/frontend/editor/src/core/hooks/tools/shared/useToolResources.test.ts b/frontend/editor/src/core/hooks/tools/shared/useToolResources.test.ts
new file mode 100644
index 0000000000..c2ff3e68d5
--- /dev/null
+++ b/frontend/editor/src/core/hooks/tools/shared/useToolResources.test.ts
@@ -0,0 +1,112 @@
+import { describe, expect, test, vi, beforeEach, afterEach } from "vitest";
+import { renderHook } from "@testing-library/react";
+import { allowConsole, expectConsole } from "@app/tests/failOnConsole";
+
+vi.mock("@app/utils/thumbnailUtils", () => ({
+  generateThumbnailForFile: vi.fn(),
+  generateThumbnailWithMetadata: vi.fn(),
+}));
+
+vi.mock("@app/contexts/PreferencesContext", () => ({
+  usePreferences: () => ({
+    preferences: { autoUnzip: false, autoUnzipFileLimit: 10 },
+  }),
+}));
+
+vi.mock("@app/services/zipFileService", () => ({
+  zipFileService: {
+    extractWithPreferences: vi.fn(),
+    createZipFromFiles: vi.fn(),
+  },
+}));
+
+import {
+  generateThumbnailForFile,
+  generateThumbnailWithMetadata,
+} from "@app/utils/thumbnailUtils";
+import { useToolResources } from "@app/hooks/tools/shared/useToolResources";
+
+const pdf = (name: string) =>
+  new File(["%PDF-1.4"], name, { type: "application/pdf" });
+
+describe("useToolResources thumbnail generation", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+  });
+
+  afterEach(() => {
+    vi.useRealTimers();
+  });
+
+  test("gives up on a thumbnail that never settles instead of hanging", async () => {
+    expectConsole.warn(/Thumbnail generation timed out for stuck\.pdf/);
+    vi.useFakeTimers();
+    // A wedged pdfium worker never replies, so the promise never settles.
+    vi.mocked(generateThumbnailForFile).mockReturnValue(new Promise(() => {}));
+
+    const { result } = renderHook(() => useToolResources());
+    const pending = result.current.generateThumbnails([pdf("stuck.pdf")]);
+
+    await vi.advanceTimersByTimeAsync(120_000);
+
+    await expect(pending).resolves.toEqual([""]);
+  });
+
+  test("gives up on metadata generation that never settles", async () => {
+    expectConsole.warn(/Thumbnail generation timed out for stuck\.pdf/);
+    vi.useFakeTimers();
+    vi.mocked(generateThumbnailWithMetadata).mockReturnValue(
+      new Promise(() => {}),
+    );
+
+    const { result } = renderHook(() => useToolResources());
+    const pending = result.current.generateThumbnailsWithMetadata([
+      pdf("stuck.pdf"),
+    ]);
+
+    await vi.advanceTimersByTimeAsync(120_000);
+
+    await expect(pending).resolves.toEqual([{ thumbnail: "", pageCount: 1 }]);
+  });
+
+  test("one stuck file does not block the rest", async () => {
+    expectConsole.warn(/Thumbnail generation timed out for stuck\.pdf/);
+    vi.useFakeTimers();
+    vi.mocked(generateThumbnailForFile)
+      .mockReturnValueOnce(new Promise(() => {}))
+      .mockResolvedValueOnce("data:image/png;base64,ok");
+
+    const { result } = renderHook(() => useToolResources());
+    const pending = result.current.generateThumbnails([
+      pdf("stuck.pdf"),
+      pdf("fine.pdf"),
+    ]);
+
+    await vi.advanceTimersByTimeAsync(120_000);
+
+    await expect(pending).resolves.toEqual(["", "data:image/png;base64,ok"]);
+  });
+
+  test("still returns real thumbnails when generation succeeds", async () => {
+    vi.mocked(generateThumbnailForFile).mockResolvedValue(
+      "data:image/png;base64,ok",
+    );
+
+    const { result } = renderHook(() => useToolResources());
+
+    await expect(
+      result.current.generateThumbnails([pdf("fine.pdf")]),
+    ).resolves.toEqual(["data:image/png;base64,ok"]);
+  });
+
+  test("a rejected thumbnail still resolves to a placeholder", async () => {
+    allowConsole.warn(/Failed to generate thumbnail/);
+    vi.mocked(generateThumbnailForFile).mockRejectedValue(new Error("boom"));
+
+    const { result } = renderHook(() => useToolResources());
+
+    await expect(
+      result.current.generateThumbnails([pdf("bad.pdf")]),
+    ).resolves.toEqual([""]);
+  });
+});
diff --git a/frontend/editor/src/core/hooks/tools/shared/useToolResources.ts b/frontend/editor/src/core/hooks/tools/shared/useToolResources.ts
index 16cbe839f0..2de0bff651 100644
--- a/frontend/editor/src/core/hooks/tools/shared/useToolResources.ts
+++ b/frontend/editor/src/core/hooks/tools/shared/useToolResources.ts
@@ -7,6 +7,34 @@ import {
 import { zipFileService } from "@app/services/zipFileService";
 import { usePreferences } from "@app/contexts/PreferencesContext";
 
+// A wedged pdfium worker never replies, so awaiting it pinned the review panel on
+// "Generating previews..." with no way out but a page reload.
+const THUMBNAIL_TIMEOUT_MS = 30_000;
+
+function withThumbnailTimeout<T>(
+  work: Promise<T>,
+  fallback: T,
+  fileName: string,
+): Promise<T> {
+  return new Promise<T>((resolve, reject) => {
+    const timer = setTimeout(() => {
+      console.warn(`Thumbnail generation timed out for ${fileName}`);
+      resolve(fallback);
+    }, THUMBNAIL_TIMEOUT_MS);
+
+    work.then(
+      (value) => {
+        clearTimeout(timer);
+        resolve(value);
+      },
+      (error) => {
+        clearTimeout(timer);
+        reject(error);
+      },
+    );
+  });
+}
+
 export const useToolResources = () => {
   const { preferences } = usePreferences();
   const [blobUrls, setBlobUrls] = useState<string[]>([]);
@@ -59,7 +87,11 @@ export const useToolResources = () => {
           console.log(
             `🖼️ Generating thumbnail for: ${file.name} (${file.type}, ${file.size} bytes)`,
           );
-          const thumbnail = await generateThumbnailForFile(file);
+          const thumbnail = await withThumbnailTimeout(
+            generateThumbnailForFile(file),
+            "",
+            file.name,
+          );
           console.log(`🖼️ Generated thumbnail for ${file.name}: SUCCESS`);
           thumbnails.push(thumbnail);
         } catch (error) {
@@ -88,7 +120,11 @@ export const useToolResources = () => {
           console.log(
             `🖼️ Generating thumbnail with metadata for: ${file.name} (${file.type}, ${file.size} bytes)`,
           );
-          const result = await generateThumbnailWithMetadata(file);
+          const result = await withThumbnailTimeout(
+            generateThumbnailWithMetadata(file),
+            { thumbnail: "", pageCount: 1 },
+            file.name,
+          );
           console.log(
             `🖼️ Generated thumbnail with metadata for ${file.name}: SUCCESS, ${result.pageCount} pages`,
           );