diff --git a/CoreEditor/package.json b/CoreEditor/package.json
index b8d6bf82b..8706fefc8 100644
--- a/CoreEditor/package.json
+++ b/CoreEditor/package.json
@@ -40,7 +40,7 @@
     "globals": "^15.15.0",
     "jest": "^30.2.0",
     "jest-environment-jsdom": "^30.2.0",
-    "markedit-api": "https://github.com/MarkEdit-app/MarkEdit-api#v0.37.0",
+    "markedit-api": "https://github.com/MarkEdit-app/MarkEdit-api#v0.38.0",
     "ts-gyb": "^0.12.0",
     "ts-jest": "^29.4.5",
     "tslib": "^2.6.2",
diff --git a/CoreEditor/src/api/ui.ts b/CoreEditor/src/api/ui.ts
index 7a552b7eb..65a04f469 100644
--- a/CoreEditor/src/api/ui.ts
+++ b/CoreEditor/src/api/ui.ts
@@ -1,5 +1,5 @@
 import { EditorView } from '@codemirror/view';
-import { MenuItem, MenuItemState, Alert, TextBox, OpenPanelOptions, PrintPanelOptions, SavePanelOptions } from 'markedit-api';
+import { MenuItem, MenuItemState, ContextMenuOptions, Alert, TextBox, OpenPanelOptions, PrintPanelOptions, SavePanelOptions } from 'markedit-api';
 
 import { WebMenuItem } from '../@types/WebMenuItem';
 import { WebPoint } from '../@types/WebPoint';
@@ -15,12 +15,19 @@ export function addMainMenuItem(spec: MenuItem | MenuItem[]): void {
   });
 }
 
-export function showContextMenu(items: MenuItem[], location?: WebPoint) {
+export function showContextMenu(items: MenuItem[], location?: WebPoint, options?: ContextMenuOptions) {
+  let { highlightedIndex } = options ?? {};
+  if (highlightedIndex !== undefined && !Number.isSafeInteger(highlightedIndex)) {
+    console.error('showContextMenu: highlightedIndex must be a safe integer.', highlightedIndex);
+    highlightedIndex = undefined;
+  }
+
   const editor = focusedEditor() ?? window.editor;
   const caretPos = editor.state.selection.main.head;
   const invokeNative = () => {
     window.nativeModules.api.showContextMenu({
       items: items.map(item => createMenuItem(item, contextActions)),
+      highlightedIndex: highlightedIndex === undefined ? undefined : (highlightedIndex as CodeGen_Int),
       location: location ?? (() => {
         const coords = editor.coordsAtPos(caretPos);
         if (coords === null) {
diff --git a/CoreEditor/src/bridge/native/api.ts b/CoreEditor/src/bridge/native/api.ts
index 65ce01400..ad03fbe5d 100644
--- a/CoreEditor/src/bridge/native/api.ts
+++ b/CoreEditor/src/bridge/native/api.ts
@@ -14,7 +14,7 @@ export interface NativeModuleAPI extends NativeModule {
   closeDocument(): Promise<boolean>;
   recentDocumentPaths(): Promise<string[]>;
   addMainMenuItems({ items }: { items: WebMenuItem[] }): void;
-  showContextMenu(args: { items: WebMenuItem[]; location: WebPoint }): void;
+  showContextMenu(args: { items: WebMenuItem[]; location: WebPoint; highlightedIndex?: CodeGen_Int }): void;
   showAlert(args: { title?: string; message?: string; buttons?: string[] }): Promise<CodeGen_Int>;
   showTextBox(args: { title?: string; placeholder?: string; defaultValue?: string }): Promise<string | undefined>;
   showOpenPanel({ options }: { options: OpenPanelOptions }): Promise<string[] | undefined>;
diff --git a/CoreEditor/test/nestedEditors.test.ts b/CoreEditor/test/nestedEditors.test.ts
index 9d7715890..ff17cc198 100644
--- a/CoreEditor/test/nestedEditors.test.ts
+++ b/CoreEditor/test/nestedEditors.test.ts
@@ -235,6 +235,99 @@ describe('context menu caret geometry', () => {
     expect(dispatch).not.toHaveBeenCalled();
   });
 
+  test.each([{}, { highlightedIndex: 0 }])('uses the cell caret with options %j', options => {
+    jest.useFakeTimers();
+    const show = prepareMenu();
+    showContextMenu([{ title: 'First' }], undefined, options);
+    expect(show).not.toHaveBeenCalled();
+
+    jest.advanceTimersByTime(50);
+    expect(show).toHaveBeenCalledWith({
+      items: [expect.objectContaining({ title: 'First' })],
+      location: { x: 80, y: 70 },
+      highlightedIndex: options.highlightedIndex,
+    });
+  });
+
+  test.each([undefined, 0, 1, 2])('uses an explicit location with highlighted index %s', highlightedIndex => {
+    const show = prepareMenu();
+    const dispatch = jest.spyOn(cell, 'dispatch');
+
+    showContextMenu([{ title: 'First' }, { separator: true }, { title: 'Last' }], { x: 1, y: 2 }, {
+      highlightedIndex,
+    });
+
+    expect(show).toHaveBeenCalledWith({
+      items: [expect.objectContaining({ title: 'First' }), expect.objectContaining({ separator: true }), expect.objectContaining({ title: 'Last' })],
+      location: { x: 1, y: 2 },
+      highlightedIndex,
+    });
+
+    expect(dispatch).not.toHaveBeenCalled();
+  });
+
+  test.each([-1, 3, Number.MIN_SAFE_INTEGER, Number.MAX_SAFE_INTEGER])(
+    'forwards out-of-range integer %s for native fallback',
+    highlightedIndex => {
+      const show = prepareMenu();
+      showContextMenu([
+        { title: 'First' },
+        { separator: true },
+        { title: 'Disabled', state: () => ({ isEnabled: false }) },
+      ], { x: 1, y: 2 }, { highlightedIndex });
+
+      expect(show).toHaveBeenCalledWith(expect.objectContaining({
+        location: { x: 1, y: 2 },
+        highlightedIndex,
+      }));
+    },
+  );
+
+  test.each([0.5, NaN, Infinity, -Infinity, Number.MAX_VALUE, Number.MAX_SAFE_INTEGER + 1, Number.MIN_SAFE_INTEGER - 1])(
+    'opens menus without a highlight for non-safe integer %s',
+    highlightedIndex => {
+      jest.useFakeTimers();
+      const show = prepareMenu();
+      jest.spyOn(console, 'error').mockImplementation(() => {});
+      for (const location of [undefined, { x: 1, y: 2 }]) {
+        showContextMenu([{ title: 'First' }], location, { highlightedIndex });
+      }
+
+      expect(show).toHaveBeenCalledTimes(1);
+      expect(show).toHaveBeenNthCalledWith(1, expect.objectContaining({
+        items: [expect.objectContaining({ title: 'First' })],
+        location: { x: 1, y: 2 },
+        highlightedIndex: undefined,
+      }));
+
+      jest.advanceTimersByTime(50);
+      expect(show).toHaveBeenCalledTimes(2);
+      expect(show).toHaveBeenNthCalledWith(2, expect.objectContaining({
+        items: [expect.objectContaining({ title: 'First' })],
+        location: { x: 80, y: 70 },
+        highlightedIndex: undefined,
+      }));
+    },
+  );
+
+  test('forwards an integer index for native fallback in an empty menu', () => {
+    const show = prepareMenu();
+    showContextMenu([], { x: 1, y: 2 }, { highlightedIndex: 0 });
+    expect(show).toHaveBeenCalledWith({ items: [], location: { x: 1, y: 2 }, highlightedIndex: 0 });
+  });
+
+  test('leaves item state evaluation to native code after scrolling to the caret', () => {
+    jest.useFakeTimers();
+    const show = prepareMenu();
+    const state = jest.fn(() => ({ isEnabled: false }));
+    showContextMenu([{ title: 'First', state }], undefined, { highlightedIndex: 0 });
+    expect(state).not.toHaveBeenCalled();
+
+    jest.advanceTimersByTime(50);
+    expect(state).not.toHaveBeenCalled();
+    expect(show).toHaveBeenCalledWith(expect.objectContaining({ highlightedIndex: 0 }));
+  });
+
   test('falls back to document geometry when no editor has focus', () => {
     jest.useFakeTimers();
     const show = prepareMenu();
diff --git a/CoreEditor/yarn.lock b/CoreEditor/yarn.lock
index ad18814f6..c09131f0a 100644
--- a/CoreEditor/yarn.lock
+++ b/CoreEditor/yarn.lock
@@ -4178,9 +4178,9 @@ __metadata:
   languageName: node
   linkType: hard
 
-"markedit-api@https://github.com/MarkEdit-app/MarkEdit-api#v0.37.0":
-  version: 0.37.0
-  resolution: "markedit-api@https://github.com/MarkEdit-app/MarkEdit-api.git#commit=7bce1077f0471a7b92d63e7e3ee0c084cea23c61"
+"markedit-api@https://github.com/MarkEdit-app/MarkEdit-api#v0.38.0":
+  version: 0.38.0
+  resolution: "markedit-api@https://github.com/MarkEdit-app/MarkEdit-api.git#commit=3f8f22bcb1067c00e1c22ae425a06ed8da710d89"
   peerDependencies:
     "@codemirror/autocomplete": ^6.0.0
     "@codemirror/commands": ^6.0.0
@@ -4193,7 +4193,7 @@ __metadata:
     "@lezer/highlight": ^1.0.0
     "@lezer/lr": ^1.0.0
     "@lezer/markdown": ^1.0.0
-  checksum: 10c0/f3b25689cc34e12c8ece581e7bcfeed43b343f64892c21cf52e86a7ffa4d5e2d9abb608f957bcb660fcebb4300b85da25fc1ddcdc3927732b052bc76b3251906
+  checksum: 10c0/15973f74e46056ebe74b3f9bac8fc250b8acafc226e0f363576e82016d7492c9ba54f017f38d10c5ed21727dd286f2022e6b591de51c6a619b189aae5f8a5e26
   languageName: node
   linkType: hard
 
@@ -4225,7 +4225,7 @@ __metadata:
     globals: "npm:^15.15.0"
     jest: "npm:^30.2.0"
     jest-environment-jsdom: "npm:^30.2.0"
-    markedit-api: "https://github.com/MarkEdit-app/MarkEdit-api#v0.37.0"
+    markedit-api: "https://github.com/MarkEdit-app/MarkEdit-api#v0.38.0"
     ts-gyb: "npm:^0.12.0"
     ts-jest: "npm:^29.4.5"
     tslib: "npm:^2.6.2"
diff --git a/MarkEdit.xcodeproj/project.pbxproj b/MarkEdit.xcodeproj/project.pbxproj
index 0334c50bb..047ad1f55 100644
--- a/MarkEdit.xcodeproj/project.pbxproj
+++ b/MarkEdit.xcodeproj/project.pbxproj
@@ -7,6 +7,9 @@
 	objects = {
 
 /* Begin PBXBuildFile section */
+		0A1100013010000000000001 /* QuickSearchUI in Frameworks */ = {isa = PBXBuildFile; productRef = 0A1100013010000000000002 /* QuickSearchUI */; };
+		0A1100013010000000000003 /* AppDelegate+QuickSearch.swift in Sources */ = {isa = PBXBuildFile; fileRef = 0A1100013010000000000004 /* AppDelegate+QuickSearch.swift */; };
+		0A1100023010000000000001 /* QuickSearchCore in Frameworks */ = {isa = PBXBuildFile; productRef = 0A1100023010000000000002 /* QuickSearchCore */; };
 		84FB00F02C6C4AED00850E94 /* AppWritingTools.swift in Sources */ = {isa = PBXBuildFile; fileRef = 84FB00EF2C6C4AED00850E94 /* AppWritingTools.swift */; };
 		8701D0A42CC12321006AF8C2 /* FileVersion in Frameworks */ = {isa = PBXBuildFile; productRef = 8701D0A32CC12321006AF8C2 /* FileVersion */; };
 		8703C175303E7DD300A896D0 /* QuickLookWindowSize.swift in Sources */ = {isa = PBXBuildFile; fileRef = 8703C171303E7DCF00A896D0 /* QuickLookWindowSize.swift */; };
@@ -24,9 +27,6 @@
 		870F17682985285B00003DA7 /* EditorViewController+Config.swift in Sources */ = {isa = PBXBuildFile; fileRef = 870F17672985285B00003DA7 /* EditorViewController+Config.swift */; };
 		870F177D29855CA500003DA7 /* MarkEditKit in Frameworks */ = {isa = PBXBuildFile; productRef = 870F177C29855CA500003DA7 /* MarkEditKit */; };
 		870F178E2985775B00003DA7 /* SharedUI in Frameworks */ = {isa = PBXBuildFile; productRef = 870F178D2985775B00003DA7 /* SharedUI */; };
-		0A1100013010000000000001 /* QuickSearchUI in Frameworks */ = {isa = PBXBuildFile; productRef = 0A1100013010000000000002 /* QuickSearchUI */; };
-		0A1100023010000000000001 /* QuickSearchCore in Frameworks */ = {isa = PBXBuildFile; productRef = 0A1100023010000000000002 /* QuickSearchCore */; };
-		0A1100013010000000000003 /* AppDelegate+QuickSearch.swift in Sources */ = {isa = PBXBuildFile; fileRef = 0A1100013010000000000004 /* AppDelegate+QuickSearch.swift */; };
 		870F17902985775B00003DA7 /* AppKitExtensions in Frameworks */ = {isa = PBXBuildFile; productRef = 870F178F2985775B00003DA7 /* AppKitExtensions */; };
 		870F17962985775B00003DA7 /* SettingsUI in Frameworks */ = {isa = PBXBuildFile; productRef = 870F17952985775B00003DA7 /* SettingsUI */; };
 		87132AA32C188FE900FD262B /* AppShortcuts.xcstrings in Resources */ = {isa = PBXBuildFile; fileRef = 87132AA22C188FE900FD262B /* AppShortcuts.xcstrings */; };
@@ -95,7 +95,6 @@
 		87AF5957302379C4006E8C6A /* AppRelauncher.swift in Sources */ = {isa = PBXBuildFile; fileRef = 87AF5956302379C3006E8C6A /* AppRelauncher.swift */; };
 		87B000000000000000000102 /* BookmarkStore.swift in Sources */ = {isa = PBXBuildFile; fileRef = 87B000000000000000000101 /* BookmarkStore.swift */; };
 		87B000000000000000000104 /* BookmarkStoreTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 87B000000000000000000103 /* BookmarkStoreTests.swift */; };
-		87D700000000000000000001 /* QuickSearchMenuTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 87D700000000000000000002 /* QuickSearchMenuTests.swift */; };
 		87B0D1022F1A4C0100B0D101 /* Localizable.xcstrings in Resources */ = {isa = PBXBuildFile; fileRef = 87B0D1012F1A4C0100B0D101 /* Localizable.xcstrings */; };
 		87B3ED5A2CBCA97D001FA6CE /* AppDocumentController.swift in Sources */ = {isa = PBXBuildFile; fileRef = 87B3ED592CBCA97D001FA6CE /* AppDocumentController.swift */; };
 		87B3ED5D2CBCADD6001FA6CE /* NSDocumentController+Extras.swift in Sources */ = {isa = PBXBuildFile; fileRef = 87B3ED5C2CBCADD6001FA6CE /* NSDocumentController+Extras.swift */; };
@@ -105,6 +104,8 @@
 		87BEF30129A88F6800596E17 /* AppCustomization.swift in Sources */ = {isa = PBXBuildFile; fileRef = 87BEF30029A88F6800596E17 /* AppCustomization.swift */; };
 		87C600000000000000000001 /* EditorDocumentTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 87C600000000000000000002 /* EditorDocumentTests.swift */; };
 		87CC48FD29CC01E100BE1441 /* TextBundle in Frameworks */ = {isa = PBXBuildFile; productRef = 87CC48FC29CC01E100BE1441 /* TextBundle */; };
+		87D700000000000000000001 /* QuickSearchMenuTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 87D700000000000000000002 /* QuickSearchMenuTests.swift */; };
+		87D800000000000000000001 /* ContextMenuTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 87D800000000000000000002 /* ContextMenuTests.swift */; };
 		87D9322E2A925C6700B20D84 /* EditorReplaceTextField.swift in Sources */ = {isa = PBXBuildFile; fileRef = 87D9322D2A925C6700B20D84 /* EditorReplaceTextField.swift */; };
 		87DA0000000000000000E00B /* UpdateInstaller.xpc in Embed XPC Services */ = {isa = PBXBuildFile; fileRef = 87DA0000000000000000E000 /* UpdateInstaller.xpc */; settings = {ATTRIBUTES = (RemoveHeadersOnCopy, ); }; };
 		87DA0000000000000000E020 /* main.swift in Sources */ = {isa = PBXBuildFile; fileRef = 87DA0000000000000000E010 /* main.swift */; };
@@ -189,6 +190,7 @@
 /* End PBXCopyFilesBuildPhase section */
 
 /* Begin PBXFileReference section */
+		0A1100013010000000000004 /* AppDelegate+QuickSearch.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "AppDelegate+QuickSearch.swift"; sourceTree = "<group>"; };
 		84FB00EF2C6C4AED00850E94 /* AppWritingTools.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = AppWritingTools.swift; sourceTree = "<group>"; };
 		8703C171303E7DCF00A896D0 /* QuickLookWindowSize.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = QuickLookWindowSize.swift; sourceTree = "<group>"; };
 		87067E2629755D5C0052E795 /* EditorStatusView.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = EditorStatusView.swift; sourceTree = "<group>"; };
@@ -276,7 +278,6 @@
 		87AF5956302379C3006E8C6A /* AppRelauncher.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = AppRelauncher.swift; sourceTree = "<group>"; };
 		87B000000000000000000101 /* BookmarkStore.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = BookmarkStore.swift; sourceTree = "<group>"; };
 		87B000000000000000000103 /* BookmarkStoreTests.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = BookmarkStoreTests.swift; sourceTree = "<group>"; };
-		87D700000000000000000002 /* QuickSearchMenuTests.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = QuickSearchMenuTests.swift; sourceTree = "<group>"; };
 		87B0D1012F1A4C0100B0D101 /* Localizable.xcstrings */ = {isa = PBXFileReference; lastKnownFileType = text.json.xcstrings; path = Localizable.xcstrings; sourceTree = "<group>"; };
 		87B3ED592CBCA97D001FA6CE /* AppDocumentController.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = AppDocumentController.swift; sourceTree = "<group>"; };
 		87B3ED5C2CBCADD6001FA6CE /* NSDocumentController+Extras.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "NSDocumentController+Extras.swift"; sourceTree = "<group>"; };
@@ -287,6 +288,8 @@
 		87C3CBFA29545944002A3436 /* MarkEditKit */ = {isa = PBXFileReference; lastKnownFileType = wrapper; path = MarkEditKit; sourceTree = "<group>"; };
 		87C600000000000000000002 /* EditorDocumentTests.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = EditorDocumentTests.swift; sourceTree = "<group>"; };
 		87C600000000000000000004 /* MarkEditMacTests.xctest */ = {isa = PBXFileReference; explicitFileType = wrapper.cfbundle; includeInIndex = 0; path = MarkEditMacTests.xctest; sourceTree = BUILT_PRODUCTS_DIR; };
+		87D700000000000000000002 /* QuickSearchMenuTests.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = QuickSearchMenuTests.swift; sourceTree = "<group>"; };
+		87D800000000000000000002 /* ContextMenuTests.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = ContextMenuTests.swift; sourceTree = "<group>"; };
 		87D9322D2A925C6700B20D84 /* EditorReplaceTextField.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = EditorReplaceTextField.swift; sourceTree = "<group>"; };
 		87DA0000000000000000E000 /* UpdateInstaller.xpc */ = {isa = PBXFileReference; explicitFileType = "wrapper.xpc-service"; includeInIndex = 0; path = UpdateInstaller.xpc; sourceTree = BUILT_PRODUCTS_DIR; };
 		87DA0000000000000000E010 /* main.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = main.swift; sourceTree = "<group>"; };
@@ -307,7 +310,6 @@
 		B0E02F672D8F77A50060DEA5 /* MarkEdit.sdef */ = {isa = PBXFileReference; lastKnownFileType = text; path = MarkEdit.sdef; sourceTree = "<group>"; };
 		CC000002300000000000001B /* EditorDocument+ClosedTab.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "EditorDocument+ClosedTab.swift"; sourceTree = "<group>"; };
 		CC000003300000000000001B /* AppDelegate+ClosedTab.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "AppDelegate+ClosedTab.swift"; sourceTree = "<group>"; };
-		0A1100013010000000000004 /* AppDelegate+QuickSearch.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "AppDelegate+QuickSearch.swift"; sourceTree = "<group>"; };
 		CC000004300000000000001B /* EditorSelectionHistory.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = EditorSelectionHistory.swift; sourceTree = "<group>"; };
 		CC000006300000000000001B /* EditorClosedTabHistory.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = EditorClosedTabHistory.swift; sourceTree = "<group>"; };
 		EE100007EEEE000000000007 /* ExtensionInstaller.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = ExtensionInstaller.swift; sourceTree = "<group>"; };
@@ -727,6 +729,7 @@
 				87C600000000000000000002 /* EditorDocumentTests.swift */,
 				87B000000000000000000103 /* BookmarkStoreTests.swift */,
 				87D700000000000000000002 /* QuickSearchMenuTests.swift */,
+				87D800000000000000000002 /* ContextMenuTests.swift */,
 			);
 			path = Tests;
 			sourceTree = "<group>";
@@ -1082,6 +1085,7 @@
 				87C600000000000000000001 /* EditorDocumentTests.swift in Sources */,
 				87B000000000000000000104 /* BookmarkStoreTests.swift in Sources */,
 				87D700000000000000000001 /* QuickSearchMenuTests.swift in Sources */,
+				87D800000000000000000001 /* ContextMenuTests.swift in Sources */,
 			);
 			runOnlyForDeploymentPostprocessing = 0;
 		};
diff --git a/MarkEditKit/Sources/Bridge/Native/Generated/NativeModuleAPI.swift b/MarkEditKit/Sources/Bridge/Native/Generated/NativeModuleAPI.swift
index f44e09136..902adb7e3 100644
--- a/MarkEditKit/Sources/Bridge/Native/Generated/NativeModuleAPI.swift
+++ b/MarkEditKit/Sources/Bridge/Native/Generated/NativeModuleAPI.swift
@@ -17,7 +17,7 @@ public protocol NativeModuleAPI: NativeModule {
   func closeDocument() async -> Bool
   func recentDocumentPaths() async -> [String]
   func addMainMenuItems(items: [WebMenuItem])
-  func showContextMenu(items: [WebMenuItem], location: WebPoint)
+  func showContextMenu(items: [WebMenuItem], location: WebPoint, highlightedIndex: Int?)
   func showAlert(title: String?, message: String?, buttons: [String]?) async -> Int
   func showTextBox(title: String?, placeholder: String?, defaultValue: String?) async -> String?
   func showOpenPanel(options: OpenPanelOptions) async -> [String]?
@@ -191,11 +191,13 @@ final class NativeBridgeAPI: NativeBridge {
     struct Message: Decodable {
       var items: [WebMenuItem]
       var location: WebPoint
+      var highlightedIndex: Int?
 
       init(from decoder: any Decoder) throws {
         let container = try decoder.container(keyedBy: BridgeFieldKey.self)
         items = try container.value("items")
         location = try container.value("location")
+        highlightedIndex = try container.value("highlightedIndex")
       }
     }
 
@@ -207,7 +209,7 @@ final class NativeBridgeAPI: NativeBridge {
       return .failure(error)
     }
 
-    module.showContextMenu(items: message.items, location: message.location)
+    module.showContextMenu(items: message.items, location: message.location, highlightedIndex: message.highlightedIndex)
     return .success(nil)
   }
 
diff --git a/MarkEditKit/Sources/Bridge/Native/Modules/EditorModuleAPI.swift b/MarkEditKit/Sources/Bridge/Native/Modules/EditorModuleAPI.swift
index a95e4c6b7..055b0ec1b 100644
--- a/MarkEditKit/Sources/Bridge/Native/Modules/EditorModuleAPI.swift
+++ b/MarkEditKit/Sources/Bridge/Native/Modules/EditorModuleAPI.swift
@@ -21,7 +21,7 @@ public protocol EditorModuleAPIDelegate: AnyObject {
   func editorAPISaveDocument(_ sender: EditorModuleAPI) async -> Bool
   func editorAPICloseDocument(_ sender: EditorModuleAPI) -> Bool
   func editorAPI(_ sender: EditorModuleAPI, addMainMenuItems items: [(String, WebMenuItem)])
-  func editorAPI(_ sender: EditorModuleAPI, showContextMenu items: [WebMenuItem], location: WebPoint)
+  func editorAPI(_ sender: EditorModuleAPI, showContextMenu items: [WebMenuItem], location: WebPoint, highlightedIndex: Int?)
   func editorAPI(
     _ sender: EditorModuleAPI,
     alertWith title: String?,
@@ -80,8 +80,8 @@ public final class EditorModuleAPI: NativeModuleAPI {
     })
   }
 
-  public func showContextMenu(items: [WebMenuItem], location: WebPoint) {
-    delegate?.editorAPI(self, showContextMenu: items, location: location)
+  public func showContextMenu(items: [WebMenuItem], location: WebPoint, highlightedIndex: Int?) {
+    delegate?.editorAPI(self, showContextMenu: items, location: location, highlightedIndex: highlightedIndex)
   }
 
   public func showAlert(title: String?, message: String?, buttons: [String]?) async -> Int {
diff --git a/MarkEditKit/Tests/MoveFileTests.swift b/MarkEditKit/Tests/MoveFileTests.swift
index 7b0095a7f..3a302a228 100644
--- a/MarkEditKit/Tests/MoveFileTests.swift
+++ b/MarkEditKit/Tests/MoveFileTests.swift
@@ -163,7 +163,7 @@ private extension MoveFileTests {
     func editorAPISaveDocument(_ sender: EditorModuleAPI) async -> Bool { false }
     func editorAPICloseDocument(_ sender: EditorModuleAPI) -> Bool { false }
     func editorAPI(_ sender: EditorModuleAPI, addMainMenuItems items: [(String, WebMenuItem)]) {}
-    func editorAPI(_ sender: EditorModuleAPI, showContextMenu items: [WebMenuItem], location: WebPoint) {}
+    func editorAPI(_ sender: EditorModuleAPI, showContextMenu items: [WebMenuItem], location: WebPoint, highlightedIndex: Int?) {}
     func editorAPI(
       _ sender: EditorModuleAPI, alertWith title: String?, message: String?, buttons: [String]?
     ) async -> Int { 0 }
diff --git a/MarkEditMac/Modules/Tests/FileVersionTests.swift b/MarkEditMac/Modules/Tests/FileVersionTests.swift
index 77822879b..2c12f591a 100644
--- a/MarkEditMac/Modules/Tests/FileVersionTests.swift
+++ b/MarkEditMac/Modules/Tests/FileVersionTests.swift
@@ -175,7 +175,7 @@ private final class EditorModuleAPIDelegateStub: EditorModuleAPIDelegate {
   func editorAPISaveDocument(_ sender: EditorModuleAPI) async -> Bool { true }
   func editorAPICloseDocument(_ sender: EditorModuleAPI) -> Bool { true }
   func editorAPI(_ sender: EditorModuleAPI, addMainMenuItems items: [(String, WebMenuItem)]) {}
-  func editorAPI(_ sender: EditorModuleAPI, showContextMenu items: [WebMenuItem], location: WebPoint) {}
+  func editorAPI(_ sender: EditorModuleAPI, showContextMenu items: [WebMenuItem], location: WebPoint, highlightedIndex: Int?) {}
   func editorAPI(
     _ sender: EditorModuleAPI,
     alertWith title: String?,
diff --git a/MarkEditMac/Sources/Editor/Controllers/EditorViewController+Delegate.swift b/MarkEditMac/Sources/Editor/Controllers/EditorViewController+Delegate.swift
index 2d3e9b77d..ef1128414 100644
--- a/MarkEditMac/Sources/Editor/Controllers/EditorViewController+Delegate.swift
+++ b/MarkEditMac/Sources/Editor/Controllers/EditorViewController+Delegate.swift
@@ -388,8 +388,8 @@ extension EditorViewController: EditorModuleAPIDelegate {
     addMainMenuItems(items: items)
   }
 
-  func editorAPI(_ sender: EditorModuleAPI, showContextMenu items: [WebMenuItem], location: WebPoint) {
-    showContextMenu(items: items, location: location.cgPoint)
+  func editorAPI(_ sender: EditorModuleAPI, showContextMenu items: [WebMenuItem], location: WebPoint, highlightedIndex: Int?) {
+    showContextMenu(items: items, location: location.cgPoint, highlightedIndex: highlightedIndex)
   }
 
   func editorAPI(
diff --git a/MarkEditMac/Sources/Editor/Controllers/EditorViewController+UI.swift b/MarkEditMac/Sources/Editor/Controllers/EditorViewController+UI.swift
index d004b7928..3f85e816a 100644
--- a/MarkEditMac/Sources/Editor/Controllers/EditorViewController+UI.swift
+++ b/MarkEditMac/Sources/Editor/Controllers/EditorViewController+UI.swift
@@ -434,12 +434,45 @@ extension EditorViewController {
     resetUserDefinedMenuItems()
   }
 
-  func showContextMenu(items: [WebMenuItem], location: CGPoint) {
+  func showContextMenu(items: [WebMenuItem], location: CGPoint, highlightedIndex: Int?) {
     let menu = createMenu(items: items, handler: bridge.api.handleContextMenuAction)
     menu.identifier = EditorWebView.userDefinedContextMenuID
 
-    NSCursor.arrow.push()
-    menu.popUp(positioning: nil, at: location, in: webView)
+    let highlightedItem: NSMenuItem? = {
+      guard let highlightedIndex, menu.items.indices.contains(highlightedIndex) else {
+        return nil
+      }
+
+      menu.update()
+      let item = menu.items[highlightedIndex]
+      return item.isEnabled && !item.isSeparatorItem ? item : nil
+    }()
+
+    let popUp = { (item: NSMenuItem?) in
+      NSCursor.arrow.push()
+      menu.popUp(positioning: item, at: location, in: self.webView)
+    }
+
+    guard let item = highlightedItem as? UserDefinedMenuItem,
+          let stateGetterID = item.stateGetterID else {
+      return popUp(highlightedItem)
+    }
+
+    Task {
+      var itemToHighlight: NSMenuItem?
+      do {
+        let state = try await bridge.api.getMenuItemState(id: stateGetterID)
+        itemToHighlight = state.isEnabled == false ? nil : item
+      } catch {
+        Logger.log(.error, "Failed to retrieve context menu item state: \(error)")
+      }
+
+      guard view.window != nil else {
+        return Logger.log(.debug, "Context menu dismissed because its editor is no longer in a window")
+      }
+
+      popUp(itemToHighlight)
+    }
   }
 
   func showAlert(title: String?, message: String?, buttons: [String]?) async -> NSApplication.ModalResponse {
diff --git a/MarkEditMac/Tests/ContextMenuTests.swift b/MarkEditMac/Tests/ContextMenuTests.swift
new file mode 100644
index 000000000..72a90fd65
--- /dev/null
+++ b/MarkEditMac/Tests/ContextMenuTests.swift
@@ -0,0 +1,132 @@
+//
+//  ContextMenuTests.swift
+//
+//  Created by cyan on 10/13/26.
+//
+
+import AppKit
+import MarkEditKit
+import XCTest
+@testable import MarkEdit
+
+@MainActor
+final class ContextMenuTests: XCTestCase {
+  func testContextMenuAPIHighlightsRequestedItem() async throws {
+    let window = NSPanel(
+      contentRect: NSRect(x: 20, y: 20, width: 600, height: 400),
+      styleMask: [.titled, .nonactivatingPanel],
+      backing: .buffered,
+      defer: false
+    )
+
+    let editor = EditorViewController(preloadDelay: 60)
+    window.contentViewController = editor
+    window.makeKeyAndOrderFront(nil)
+    defer { window.orderOut(nil) }
+
+    let api = EditorModuleAPI(delegate: editor)
+    let cases: [(index: Int?, expected: Int?)] = [
+      (nil, nil), (0, 0), (2, 2), (1, nil), (3, nil), (-1, nil), (100, nil),
+    ]
+
+    for testCase in cases {
+      var parameters: [String: Any] = [
+        "items": [
+          ["title": "First", "separator": false, "actionID": "first"],
+          ["separator": true],
+          ["title": "Last", "separator": false, "actionID": "last"],
+          ["title": "Disabled", "separator": false],
+        ],
+        "location": ["x": 20, "y": 20],
+      ]
+
+      parameters["highlightedIndex"] = testCase.index
+      try await checkHighlight(in: editor, expectedIndex: testCase.expected) {
+        let result = await api.bridge.invoke(
+          method: "showContextMenu",
+          parameters: try JSONSerialization.data(withJSONObject: parameters)
+        )
+
+        _ = try XCTUnwrap(result).get()
+      }
+    }
+  }
+
+  func testContextMenuAwaitsJavaScriptItemState() async throws {
+    let window = NSPanel(
+      contentRect: NSRect(x: 20, y: 20, width: 600, height: 400),
+      styleMask: [.titled, .nonactivatingPanel],
+      backing: .buffered,
+      defer: false
+    )
+
+    let editor = EditorViewController()
+    window.contentViewController = editor
+    window.makeKeyAndOrderFront(nil)
+    defer { window.orderOut(nil) }
+
+    let deadline = ContinuousClock.now + .seconds(10)
+    while !editor.hasFinishedLoading, ContinuousClock.now < deadline {
+      try await Task.sleep(for: .milliseconds(10))
+    }
+
+    XCTAssertTrue(editor.hasFinishedLoading)
+    _ = try await editor.bridge.core.resetEditor(text: "Test", selectionRange: nil, documentChanged: true)
+
+    let cases: [(stateBody: String, expected: Int?)] = [
+      ("return {};", 0),
+      ("return { isEnabled: true };", 0),
+      ("return { isEnabled: false };", nil),
+      ("throw new Error('Expected state failure');", nil),
+    ]
+
+    for testCase in cases {
+      try await checkHighlight(in: editor, expectedIndex: testCase.expected) {
+        _ = try await editor.webView.evaluateJavaScript("""
+          MarkEdit.showContextMenu([
+            { title: 'First', action() {}, state() { \(testCase.stateBody) } }
+          ], { x: 20, y: 20 }, { highlightedIndex: 0 });
+          true;
+          """)
+      }
+    }
+  }
+
+  private func checkHighlight(
+    in editor: EditorViewController,
+    expectedIndex: Int?,
+    showMenu: () async throws -> Void
+  ) async throws {
+    let checked = expectation(description: "Checked context menu highlight")
+    let timer = Timer(
+      timeInterval: 0.1,
+      target: self,
+      selector: #selector(checkContextMenuHighlight(_:)),
+      userInfo: (editor, expectedIndex, checked),
+      repeats: false
+    )
+
+    RunLoop.main.add(timer, forMode: .eventTracking)
+    defer { timer.invalidate() }
+
+    try await showMenu()
+    await fulfillment(of: [checked], timeout: 2)
+  }
+
+  @objc private func checkContextMenuHighlight(_ timer: Timer) {
+    guard let (editor, expectedIndex, checked) = timer.userInfo as? (EditorViewController, Int?, XCTestExpectation),
+          let menu = editor.presentedMenu else {
+      XCTFail("Missing context menu")
+      return
+    }
+
+    if let expectedIndex {
+      XCTAssertIdentical(menu.highlightedItem, menu.items[expectedIndex])
+    } else {
+      XCTAssertNil(menu.highlightedItem)
+    }
+
+    checked.fulfill()
+    menu.cancelTracking()
+  }
+}