diff --git a/apps/desktop/src/lib/__tests__/editor/keyboardShortcuts.spec.ts b/apps/desktop/src/lib/__tests__/editor/keyboardShortcuts.spec.ts
index 6a8b32756d..835257eb14 100644
--- a/apps/desktop/src/lib/__tests__/editor/keyboardShortcuts.spec.ts
+++ b/apps/desktop/src/lib/__tests__/editor/keyboardShortcuts.spec.ts
@@ -17,6 +17,7 @@ import {
   tabSwitcherDirectionFromShortcut,
 } from "@/lib/editor/keyboardShortcuts";
 import { formatShortcutDisplay, isMacShortcutPlatform } from "@/lib/editor/shortcutDisplay";
+import { shortcutToCodeMirrorKey } from "@/lib/editor/shortcutRegistry";
 
 describe("keyboard shortcut matching", () => {
   it("records modifier-only mouse shortcut settings", () => {
@@ -44,6 +45,31 @@ describe("keyboard shortcut matching", () => {
     expect(eventToShortcut({ key: "+", ctrlKey: true, shiftKey: true }, "Win32")).toBe("Shift+Mod+Plus");
   });
 
+  it("records shifted punctuation by its unshifted key so CodeMirror can resolve the binding", () => {
+    // CodeMirror registers and looks up "Shift-" bindings against the physical
+    // key ("/"), never the shifted character ("?"), so recording "?" produced a
+    // binding that could never fire.
+    expect(eventToShortcut({ key: "?", code: "Slash", ctrlKey: true, shiftKey: true }, "Win32")).toBe("Shift+Mod+/");
+    expect(shortcutToCodeMirrorKey(eventToShortcut({ key: "?", code: "Slash", ctrlKey: true, shiftKey: true }, "Win32")!)).toBe("Shift-Mod-/");
+
+    expect(eventToShortcut({ key: "!", code: "Digit1", ctrlKey: true, shiftKey: true }, "Win32")).toBe("Shift+Mod+1");
+    expect(eventToShortcut({ key: ":", code: "Semicolon", altKey: true, shiftKey: true }, "Win32")).toBe("Shift+Alt+;");
+  });
+
+  it("matches a press against a shortcut stored with the unshifted key", () => {
+    const press = { key: "?", code: "Slash", ctrlKey: true, shiftKey: true };
+    expect(matchesShortcut(press, "Shift+Mod+/", "Win32")).toBe(true);
+    // The shifted character still matches, so shortcuts saved by older versions keep working.
+    expect(matchesShortcut(press, "Shift+Mod+?", "Win32")).toBe(true);
+    // A different physical key must not match.
+    expect(matchesShortcut({ key: "?", code: "Period", ctrlKey: true, shiftKey: true }, "Shift+Mod+/", "Win32")).toBe(false);
+  });
+
+  it("leaves unshifted and letter keys untouched", () => {
+    expect(eventToShortcut({ key: "/", code: "Slash", ctrlKey: true }, "Win32")).toBe("Mod+/");
+    expect(eventToShortcut({ key: "A", code: "KeyA", ctrlKey: true, shiftKey: true }, "Win32")).toBe("Shift+Mod+A");
+  });
+
   it.each([
     ["¨", "KeyU", "Shift+Alt+U"],
     ["Ò", "KeyL", "Shift+Alt+L"],
@@ -89,13 +115,37 @@ describe("keyboard shortcut matching", () => {
     const combinedShortcut = eventToShortcut({ key: "b", ctrlKey: true, metaKey: true, shiftKey: true, altKey: true }, "MacIntel");
 
     expect(combinedShortcut).toBe("Shift+Ctrl+Mod+Alt+B");
-    expect(matchesShortcut({ key: "b", ctrlKey: true, metaKey: true, shiftKey: true, altKey: true }, combinedShortcut!, "MacIntel")).toBe(true);
+    expect(
+      matchesShortcut(
+        {
+          key: "b",
+          ctrlKey: true,
+          metaKey: true,
+          shiftKey: true,
+          altKey: true,
+        },
+        combinedShortcut!,
+        "MacIntel",
+      ),
+    ).toBe(true);
     expect(matchesShortcut({ key: "b", ctrlKey: true, shiftKey: true, altKey: true }, combinedShortcut!, "MacIntel")).toBe(false);
     expect(matchesShortcut({ key: "b", metaKey: true, shiftKey: true, altKey: true }, combinedShortcut!, "MacIntel")).toBe(false);
 
     const nonMacCombinedShortcut = eventToShortcut({ key: "b", ctrlKey: true, metaKey: true, shiftKey: true, altKey: true }, "Win32");
     expect(nonMacCombinedShortcut).toBe("Shift+Mod+Meta+Alt+B");
-    expect(matchesShortcut({ key: "b", ctrlKey: true, metaKey: true, shiftKey: true, altKey: true }, nonMacCombinedShortcut!, "Win32")).toBe(true);
+    expect(
+      matchesShortcut(
+        {
+          key: "b",
+          ctrlKey: true,
+          metaKey: true,
+          shiftKey: true,
+          altKey: true,
+        },
+        nonMacCombinedShortcut!,
+        "Win32",
+      ),
+    ).toBe(true);
     expect(matchesShortcut({ key: "b", ctrlKey: true, shiftKey: true, altKey: true }, nonMacCombinedShortcut!, "Win32")).toBe(false);
     expect(matchesShortcut({ key: "b", metaKey: true, shiftKey: true, altKey: true }, nonMacCombinedShortcut!, "Win32")).toBe(false);
   });
@@ -109,7 +159,11 @@ describe("keyboard shortcut matching", () => {
     const isMac = isMacShortcutPlatform();
     const platformModEvent = isMac ? { key: "\\", metaKey: true } : { key: "\\", ctrlKey: true };
 
-    expect(isExecuteSqlInNewResultTabShortcut(platformModEvent, { executeSqlInNewResultTab: "Mod+\\" })).toBe(true);
+    expect(
+      isExecuteSqlInNewResultTabShortcut(platformModEvent, {
+        executeSqlInNewResultTab: "Mod+\\",
+      }),
+    ).toBe(true);
     expect(isExecuteSqlInNewResultTabShortcut({ ...platformModEvent, shiftKey: true }, { executeSqlInNewResultTab: "Mod+\\" })).toBe(false);
     expect(isExecuteSqlInNewResultTabShortcut({ key: "\\", ctrlKey: true }, { executeSqlInNewResultTab: "Mod+\\" })).toBe(!isMac);
     expect(isExecuteSqlInNewResultTabShortcut({ key: "\\", metaKey: true }, { executeSqlInNewResultTab: "Mod+\\" })).toBe(true);
@@ -118,7 +172,11 @@ describe("keyboard shortcut matching", () => {
   it("matches the configurable Zen mode shortcut", () => {
     const platformModEvent = isMacShortcutPlatform() ? { key: "F12", metaKey: true, shiftKey: true } : { key: "F12", ctrlKey: true, shiftKey: true };
 
-    expect(isToggleZenModeShortcut(platformModEvent, { toggleZenMode: "Shift+Mod+F12" })).toBe(true);
+    expect(
+      isToggleZenModeShortcut(platformModEvent, {
+        toggleZenMode: "Shift+Mod+F12",
+      }),
+    ).toBe(true);
     expect(isToggleZenModeShortcut({ ...platformModEvent, shiftKey: false }, { toggleZenMode: "Shift+Mod+F12" })).toBe(false);
     expect(isToggleZenModeShortcut(platformModEvent, { toggleZenMode: "" })).toBe(false);
   });
diff --git a/apps/desktop/src/lib/editor/keyboardShortcuts.ts b/apps/desktop/src/lib/editor/keyboardShortcuts.ts
index 9fd2d8c48e..e911939f8b 100644
--- a/apps/desktop/src/lib/editor/keyboardShortcuts.ts
+++ b/apps/desktop/src/lib/editor/keyboardShortcuts.ts
@@ -17,8 +17,51 @@ function normalizeKey(key: string): string {
   return key.length === 1 ? key.toLowerCase() : key;
 }
 
+// Physical keys whose unshifted character CodeMirror always registers bindings
+// under. `KeyboardEvent.key` reports the *shifted* character instead ("/" -> "?",
+// "1" -> "!"), so a shortcut recorded from that character can never match the
+// binding CodeMirror looks up. Letters are excluded: they already round-trip
+// because `shortcutToCodeMirrorKey` lowercases them.
+const BASE_KEY_BY_CODE: Record<string, string> = {
+  Digit0: "0",
+  Digit1: "1",
+  Digit2: "2",
+  Digit3: "3",
+  Digit4: "4",
+  Digit5: "5",
+  Digit6: "6",
+  Digit7: "7",
+  Digit8: "8",
+  Digit9: "9",
+  Backquote: "`",
+  Minus: "-",
+  Equal: "=",
+  BracketLeft: "[",
+  BracketRight: "]",
+  Backslash: "\\",
+  Semicolon: ";",
+  Quote: "'",
+  Comma: ",",
+  Period: ".",
+  Slash: "/",
+};
+
+/**
+ * The unshifted character for a shifted punctuation/digit press, or null when
+ * the event is not one. Mirrors CodeMirror's `base[event.keyCode]` table, which
+ * is what its keymap resolves `Shift-` bindings against.
+ */
+function baseKeyForShiftedEvent(event: ShortcutLikeEvent): string | null {
+  if (!event.shiftKey || event.key.length !== 1) return null;
+  const baseKey = BASE_KEY_BY_CODE[event.code ?? ""];
+  return baseKey && baseKey !== event.key ? baseKey : null;
+}
+
 function matchesShortcutKey(event: ShortcutLikeEvent, key: string, platform = globalThis.navigator?.platform || ""): boolean {
   if (normalizeKey(event.key) === normalizeKey(key)) return true;
+  // Shortcuts store the unshifted character for shifted punctuation/digits (see
+  // baseKeyForShiftedEvent), so match those against the physical key too.
+  if (baseKeyForShiftedEvent(event) === normalizeKey(key)) return true;
   // KeyboardEvent.code 回退：event.key 随布局/修饰键变形时按物理键位匹配
   // （macOS Option+字母 → 变形字符如 ⌥W="∑"；俄文等非拉丁布局 → "Ц"）。
   // 仅限 Alt 组合键场景
@@ -41,6 +84,10 @@ function shortcutKeyNameFromEvent(event: ShortcutLikeEvent, platform: string): s
   if (event.altKey && isMacShortcutPlatform(platform) && /^Key[A-Z]$/.test(event.code ?? "")) {
     return event.code!.slice(3);
   }
+  // Record "Shift+Mod+/" rather than "Shift+Mod+?" so the CodeMirror binding
+  // ("Shift-Ctrl-/") is one the keymap actually resolves for this key press.
+  const baseKey = baseKeyForShiftedEvent(event);
+  if (baseKey) return shortcutKeyName(baseKey);
   return shortcutKeyName(event.key);
 }