diff --git a/src/main/index.ts b/src/main/index.ts
index 261af8b..eab3d02 100644
--- a/src/main/index.ts
+++ b/src/main/index.ts
@@ -201,48 +201,59 @@ function sanitizeName(name: string): string {
 ipcMain.handle("folio:newBookNamed", async (_e, name: string) => {
   const title = (name || "").trim();
   if (!title) return { error: "Please provide a book name." };
-  const base = app.getPath("documents");
-  const folder = sanitizeName(title) || "Untitled";
-  let target = path.join(base, folder);
-  let n = 2;
-  while (hasBook(target) || fs.existsSync(target)) {
-    target = path.join(base, `${folder} ${n}`);
-    n++;
+  try {
+    const base = app.getPath("documents");
+    const folder = sanitizeName(title) || "Untitled";
+    let target = path.join(base, folder);
+    let n = 2;
+    while (hasBook(target) || fs.existsSync(target)) {
+      target = path.join(base, `${folder} ${n}`);
+      n++;
+    }
+    const meta = createBook(target, title);
+    if (process.env.FOLIO_SELF_TEST !== "1") {
+      addRecent({ path: target, title: meta.title, lastOpened: new Date().toISOString() });
+    }
+    bookPath = target;
+    mainWindow?.setTitle(`${meta.title} — Folio`);
+    refreshMenu();
+    getWindow()?.webContents.send("folio:bookOpened", { path: target, title: meta.title });
+    return { path: target, title: meta.title };
+  } catch (err) {
+    return { error: err instanceof Error ? err.message : String(err) };
   }
-  const meta = createBook(target, title);
-  if (process.env.FOLIO_SELF_TEST !== "1") {
-    addRecent({ path: target, title: meta.title, lastOpened: new Date().toISOString() });
-  }
-  bookPath = target;
-  mainWindow?.setTitle(`${meta.title} — Folio`);
-  refreshMenu();
-  getWindow()?.webContents.send("folio:bookOpened", { path: target, title: meta.title });
-  return { path: target, title: meta.title };
 });
 
 ipcMain.handle("folio:deleteBook", async (_e, p: string) => {
   try {
-    // Always drop the recent entry, even if the folder is gone or was moved,
-    // so stale/missing books can be cleared from the list.
-    removeRecent(p);
     if (!hasBook(p)) {
+      // Stale recent entry: nothing to trash, just clear it from the list.
+      removeRecent(p);
       if (bookPath === p) bookPath = null;
       refreshMenu();
       return { ok: true };
     }
-    // Move to the system trash rather than permanently erasing, so an
-    // accidental delete can be undone from the desktop trash.
+    // Move to the system trash rather than permanently erasing. If the
+    // trash refuses, STOP and report instead of silently destroying a whole
+    // book directory — an unrecoverable rmSync here used to masquerade as a
+    // safe "move to trash".
+    let trashed = false;
     try {
       await shell.trashItem(p);
+      trashed = true;
     } catch {
-      // Fall back to a permanent delete only when the system trash is
-      // unavailable (e.g. headless environments). On a normal desktop the
-      // book is moved to the trash and remains recoverable.
-      fs.rmSync(p, { recursive: true, force: true });
+      return {
+        error:
+          "Could not move the book to the system trash, so it was left untouched. " +
+          "Delete it manually from your file manager if you are sure.",
+      };
     }
+    removeRecent(p);
     if (bookPath === p) bookPath = null;
     refreshMenu();
-    return { ok: true };
+    // In-app Undo reads the Linux home trash layout; on other platforms the
+    // OS trash is still recoverable by hand, so no false promise is made.
+    return { ok: true, trashed, canUndoRestore: process.platform === "linux" };
   } catch (e) {
     return { error: (e as Error).message };
   }
@@ -289,8 +300,14 @@ ipcMain.handle("folio:getRecents", (): Recent[] => listRecents());
 ipcMain.handle("folio:closeBook", () => {
   bookPath = null;
   mainWindow?.setTitle("Folio");
-  refreshMenu();
+  // Notify the renderer BEFORE rebuilding the menu: a refreshMenu failure
+  // must not leave main with no book while the renderer still shows one.
   getWindow()?.webContents.send("folio:bookClosed");
+  try {
+    refreshMenu();
+  } catch (err) {
+    console.error("[folio] refreshMenu after close failed:", err);
+  }
   return true;
 });
 
@@ -457,28 +474,36 @@ function currentBookTitle(): string {
 }
 
 ipcMain.handle("folio:exportMarkdown", async () => {
-  const bp = requireBook();
-  const { canceled, filePath } = await showSaveDialog({
-    title: "Export combined Markdown",
-    defaultPath: `${currentBookTitle()}.md`,
-    filters: [{ name: "Markdown", extensions: ["md"] }],
-  });
-  if (canceled || !filePath) return { canceled: true } as const;
-  fs.writeFileSync(filePath, combineMarkdown(bp), "utf-8");
-  return { ok: true, filePath };
+  try {
+    const bp = requireBook();
+    const { canceled, filePath } = await showSaveDialog({
+      title: "Export combined Markdown",
+      defaultPath: `${currentBookTitle()}.md`,
+      filters: [{ name: "Markdown", extensions: ["md"] }],
+    });
+    if (canceled || !filePath) return { canceled: true } as const;
+    fs.writeFileSync(filePath, combineMarkdown(bp), "utf-8");
+    return { ok: true, filePath };
+  } catch (err) {
+    return { error: err instanceof Error ? err.message : String(err) };
+  }
 });
 
 ipcMain.handle("folio:exportZip", async () => {
-  const bp = requireBook();
-  const { canceled, filePath } = await showSaveDialog({
-    title: "Export book bundle (ZIP)",
-    defaultPath: `${currentBookTitle()}.zip`,
-    filters: [{ name: "ZIP Archive", extensions: ["zip"] }],
-  });
-  if (canceled || !filePath) return { canceled: true } as const;
-  const buf = await buildZip(bp);
-  fs.writeFileSync(filePath, buf);
-  return { ok: true, filePath };
+  try {
+    const bp = requireBook();
+    const { canceled, filePath } = await showSaveDialog({
+      title: "Export book bundle (ZIP)",
+      defaultPath: `${currentBookTitle()}.zip`,
+      filters: [{ name: "ZIP Archive", extensions: ["zip"] }],
+    });
+    if (canceled || !filePath) return { canceled: true } as const;
+    const buf = await buildZip(bp);
+    fs.writeFileSync(filePath, buf);
+    return { ok: true, filePath };
+  } catch (err) {
+    return { error: err instanceof Error ? err.message : String(err) };
+  }
 });
 
 // Export the Full Book view as a PDF. The renderer shows only the assembled
@@ -489,10 +514,13 @@ ipcMain.handle("folio:exportZip", async () => {
 ipcMain.handle("folio:exportPdf", async (_e, chapterIds?: string[] | null) => {
   try {
     requireBook();
-    const selected = Array.isArray(chapterIds) && chapterIds.length > 0;
-    if (selected && chapterIds!.length === 0) {
+    // An explicitly empty selection is an error; undefined/null means the
+    // whole book. The old guard checked length>0 before comparing to zero,
+    // so it could never fire and empty arrays fell through to a full export.
+    if (Array.isArray(chapterIds) && chapterIds.length === 0) {
       return { error: "Select at least one chapter to export." };
     }
+    const selected = Array.isArray(chapterIds) && chapterIds.length > 0;
     const base = currentBookTitle();
     const suffix = selected ? " - Selected Chapters" : "";
     let filePath: string;
@@ -529,10 +557,12 @@ ipcMain.handle("folio:exportPdf", async (_e, chapterIds?: string[] | null) => {
 async function exportOffice(format: "docx" | "odt", chapterIds?: string[] | null) {
   try {
     const bp = requireBook();
-    const selected = Array.isArray(chapterIds) && chapterIds.length > 0;
-    if (selected && chapterIds!.length === 0) {
+    // Same fix as the PDF path: an explicitly empty array is an error,
+    // undefined/null means the whole book.
+    if (Array.isArray(chapterIds) && chapterIds.length === 0) {
       return { error: "Select at least one chapter to export." };
     }
+    const selected = Array.isArray(chapterIds) && chapterIds.length > 0;
     const ext = format;
     const envKey = format === "docx" ? "FOLIO_TEST_DOCX" : "FOLIO_TEST_ODT";
     const base = currentBookTitle();
@@ -622,30 +652,34 @@ ipcMain.handle("folio:saveChapterDoc", (_e, id: string, doc: unknown) => {
 // Copy a user-chosen image into the book's assets/ directory and return a path
 // relative to the book root (e.g. "assets/photo.png") for embedding.
 ipcMain.handle("folio:importImageAsset", async () => {
-  const bp = requireBook();
-  const { canceled, filePaths } = await showOpenDialog({
-    title: "Insert image",
-    properties: ["openFile"],
-    filters: [
-      { name: "Images", extensions: ["png", "jpg", "jpeg", "gif", "webp", "svg", "bmp"] },
-    ],
-  });
-  if (canceled || !filePaths.length) return { canceled: true } as const;
-  const src = filePaths[0];
-  const dir = path.join(bp, "assets");
-  fs.mkdirSync(dir, { recursive: true });
-  const base = path.basename(src);
-  const ext = path.extname(base);
-  const stem = path.basename(base, ext);
-  let name = base;
-  let counter = 2;
-  while (fs.existsSync(path.join(dir, name))) {
-    name = `${stem}-${counter}${ext}`;
-    counter += 1;
+  try {
+    const bp = requireBook();
+    const { canceled, filePaths } = await showOpenDialog({
+      title: "Insert image",
+      properties: ["openFile"],
+      filters: [
+        { name: "Images", extensions: ["png", "jpg", "jpeg", "gif", "webp", "svg", "bmp"] },
+      ],
+    });
+    if (canceled || !filePaths.length) return { canceled: true } as const;
+    const src = filePaths[0];
+    const dir = path.join(bp, "assets");
+    fs.mkdirSync(dir, { recursive: true });
+    const base = path.basename(src);
+    const ext = path.extname(base);
+    const stem = path.basename(base, ext);
+    let name = base;
+    let counter = 2;
+    while (fs.existsSync(path.join(dir, name))) {
+      name = `${stem}-${counter}${ext}`;
+      counter += 1;
+    }
+    fs.copyFileSync(src, path.join(dir, name));
+    const relPath = `assets/${name}`;
+    return { ok: true, name, relPath };
+  } catch (err) {
+    return { error: err instanceof Error ? err.message : String(err) };
   }
-  fs.copyFileSync(src, path.join(dir, name));
-  const relPath = `assets/${name}`;
-  return { ok: true, name, relPath };
 });
 
 ipcMain.handle("folio:copyText", (_e, text: string) => {
@@ -686,10 +720,14 @@ ipcMain.on("folio:context-menu", (event, x: number, y: number) => {
 // "light" in the renderer, so it is normalized here too.
 ipcMain.handle("folio:getTheme", () => getSetting("theme", "light"));
 ipcMain.handle("folio:setTheme", (_e, id: unknown) => {
-  const theme =
-    typeof id === "string" && id && id !== "default" ? id : "light";
-  setSetting("theme", theme);
-  return { ok: true };
+  try {
+    const theme =
+      typeof id === "string" && id && id !== "default" ? id : "light";
+    setSetting("theme", theme);
+    return { ok: true };
+  } catch (err) {
+    return { error: err instanceof Error ? err.message : String(err) };
+  }
 });
 
 // Editor zoom preference (percentage). Persisted app-wide, not per book, so the
@@ -699,9 +737,13 @@ ipcMain.handle("folio:getZoom", () => {
   return Number.isFinite(z) && z > 0 ? Math.round(z) : 100;
 });
 ipcMain.handle("folio:setZoom", (_e, pct: unknown) => {
-  const z = typeof pct === "number" && Number.isFinite(pct) ? Math.round(pct) : 100;
-  setSetting("zoom", z);
-  return { ok: true };
+  try {
+    const z = typeof pct === "number" && Number.isFinite(pct) ? Math.round(pct) : 100;
+    setSetting("zoom", z);
+    return { ok: true };
+  } catch (err) {
+    return { error: err instanceof Error ? err.message : String(err) };
+  }
 });
 
 // Backup location preference. Backup reads/writes settings through the
@@ -709,31 +751,39 @@ ipcMain.handle("folio:setZoom", (_e, pct: unknown) => {
 bindBackupSettings({ get: getSetting, set: setSetting });
 ipcMain.handle("folio:getBackupLocation", () => getRecoveryRoot());
 ipcMain.handle("folio:setBackupLocation", (_e, loc: unknown) => {
-  const s = typeof loc === "string" ? loc.trim() : "";
-  setRecoveryRoot(s);
-  return { ok: true };
+  try {
+    const s = typeof loc === "string" ? loc.trim() : "";
+    setRecoveryRoot(s);
+    return { ok: true };
+  } catch (err) {
+    return { error: err instanceof Error ? err.message : String(err) };
+  }
 });
 
 ipcMain.handle("folio:importAttachment", async () => {
-  const bp = requireBook();
-  const { canceled, filePaths } = await showOpenDialog({
-    title: "Attach a file",
-    properties: ["openFile"],
-  });
-  if (canceled || !filePaths.length) return { canceled: true } as const;
-  const src = filePaths[0];
-  const dir = path.join(bp, "attachments");
-  fs.mkdirSync(dir, { recursive: true });
-  const base = path.basename(src);
-  const ext = path.extname(base);
-  const stem = path.basename(base, ext);
-  let name = base;
-  let counter = 2;
-  while (fs.existsSync(path.join(dir, name))) {
-    name = `${stem}-${counter}${ext}`;
-    counter += 1;
+  try {
+    const bp = requireBook();
+    const { canceled, filePaths } = await showOpenDialog({
+      title: "Attach a file",
+      properties: ["openFile"],
+    });
+    if (canceled || !filePaths.length) return { canceled: true } as const;
+    const src = filePaths[0];
+    const dir = path.join(bp, "attachments");
+    fs.mkdirSync(dir, { recursive: true });
+    const base = path.basename(src);
+    const ext = path.extname(base);
+    const stem = path.basename(base, ext);
+    let name = base;
+    let counter = 2;
+    while (fs.existsSync(path.join(dir, name))) {
+      name = `${stem}-${counter}${ext}`;
+      counter += 1;
+    }
+    fs.copyFileSync(src, path.join(dir, name));
+    const relPath = path.relative(bp, path.join(dir, name)).split(path.sep).join("/");
+    return { ok: true, name, relPath };
+  } catch (err) {
+    return { error: err instanceof Error ? err.message : String(err) };
   }
-  fs.copyFileSync(src, path.join(dir, name));
-  const relPath = path.relative(bp, path.join(dir, name)).split(path.sep).join("/");
-  return { ok: true, name, relPath };
 });
diff --git a/src/main/menu.ts b/src/main/menu.ts
index cc6b848..497cedc 100644
--- a/src/main/menu.ts
+++ b/src/main/menu.ts
@@ -18,11 +18,19 @@ export function buildMenu(
   const recents = listRecents();
 
   const recentItems: MenuItem[] = recents.length
-    ? recents.map((r: Recent) => ({
-        label: r.title.length ? `${r.title} — ${path.dirname(r.path)}` : path.basename(r.path),
-        tooltip: r.path,
-        click: () => getWindow()?.webContents.send("folio:open-recent", r.path),
-      }))
+    ? recents.map((r: Recent) => {
+        // A folio.json with a null/missing title used to throw here and,
+        // at startup, take the whole app down before any window existed.
+        const title = typeof r.title === "string" ? r.title.trim() : "";
+        const label = title
+          ? `${title} — ${path.dirname(r.path)}`
+          : path.basename(r.path);
+        return {
+          label,
+          tooltip: r.path,
+          click: () => getWindow()?.webContents.send("folio:open-recent", r.path),
+        };
+      })
     : [{ label: "(no recent books)", enabled: false }];
 
   const fileMenu: MenuItem = {
diff --git a/src/main/recents.ts b/src/main/recents.ts
index 8044cf3..5666ca8 100644
--- a/src/main/recents.ts
+++ b/src/main/recents.ts
@@ -61,10 +61,13 @@ export function listRecents(): (Recent & { missing?: boolean })[] {
   // Keep every saved entry so a book never "disappears" from the list just
   // because its folder moved or was renamed. Mark entries whose book can't be
   // found so the UI can show them as missing instead of hiding them.
+  // Dedupe by PATH: keying on title used to hide genuinely distinct books
+  // that happened to share a display name ("Untitled"), making one of them
+  // unreachable from the recents menu.
   const seen = new Set<string>();
   const deduped: (Recent & { missing?: boolean })[] = [];
   for (const r of loadRaw(recentsFilePath())) {
-    const key = (r.title || r.path).toLowerCase();
+    const key = path.resolve(r.path);
     if (seen.has(key)) continue;
     seen.add(key);
     deduped.push({ ...r, missing: !hasBook(r.path) });
diff --git a/src/renderer/book.ts b/src/renderer/book.ts
index 46e76e9..267acbe 100644
--- a/src/renderer/book.ts
+++ b/src/renderer/book.ts
@@ -1803,6 +1803,10 @@ const tmp = createTiptapEditor(host);
             return;
           }
           await renderRecents();
+          // Only promise an in-app Undo where restore actually works (Linux
+          // home trash). Elsewhere the book sits in the OS trash, which the
+          // user can restore manually — no false "Undo" button.
+          if (!(res as { canUndoRestore?: boolean }).canUndoRestore) return;
           showUndoToast(`Deleted "${r.title || r.path}"`, async () => {
             const rr = await api.restoreBook(r.path);
             if (rr && "error" in rr) {