diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3e2b3c3d0..1ea86c27c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -33,6 +33,8 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ### Improvements
 
+* Add support for selecting menu items in `Navset` controllers to improve dropdown navigation test coverage. (#2066)
+
 * `input_date()`, `input_date_range()`, `update_date()`, and `update_date_range()` now supports `""` for values, mins, and maxes. In this case, no date will be specified on the client. (#1713) (#1689)
 
 * Restricted the allowable types of the `choices` parameter of `input_select()`, `input_selectize()`, `update_select()`, and `update_selectize()` to actual set of allowable types (previously, the type was suggesting HTML-like values were supported). (#2048)
diff --git a/shiny/playwright/controller/_navs.py b/shiny/playwright/controller/_navs.py
index 8db173d50..7a5630406 100644
--- a/shiny/playwright/controller/_navs.py
+++ b/shiny/playwright/controller/_navs.py
@@ -145,11 +145,35 @@ def click(self, *, timeout: Timeout = None) -> None:
         """
         Clicks the nav panel.
 
+        If the nav panel is inside a dropdown, playwright will first open the dropdown before selecting the nav panel.
+
         Parameters
         ----------
         timeout
             The maximum time to wait for the nav panel to be visible and interactable. Defaults to `None`.
         """
+
+        parent_ul_loc = self.loc.locator("..").locator("..")
+
+        parent_ul_cls = parent_ul_loc.element_handle().get_attribute("class")
+        cls_menu_regex = re.compile(rf"(^|\s+){re.escape('dropdown-menu')}(\s+|$)")
+        cls_show_regex = re.compile(rf"(^|\s+){re.escape('show')}(\s+|$)")
+        cls_dropdown_regex = re.compile(rf"(^|\s+){re.escape('dropdown')}(\s+|$)")
+
+        # If the item is in a dropdown and the dropdown is closed
+        if (
+            parent_ul_cls
+            and cls_menu_regex.search(parent_ul_cls)
+            and not cls_show_regex.search(parent_ul_cls)
+        ):
+            grandparent_li_loc = parent_ul_loc.locator("..")
+            gnd_li_cls = grandparent_li_loc.element_handle().get_attribute("class")
+
+            # Confirm it is a dropdown
+            if gnd_li_cls and cls_dropdown_regex.search(gnd_li_cls):
+                # click the grandparent list item to open it before clicking the target item
+                grandparent_li_loc.click()
+
         self.loc.click(timeout=timeout)
 
     def expect_active(self, value: bool, *, timeout: Timeout = None) -> None:
diff --git a/tests/playwright/shiny/components/nav/navset_menu/app-express.py b/tests/playwright/shiny/components/nav/navset_menu/app-express.py
new file mode 100644
index 000000000..d4e3d6c5e
--- /dev/null
+++ b/tests/playwright/shiny/components/nav/navset_menu/app-express.py
@@ -0,0 +1,52 @@
+from shiny.express import input, render, ui
+
+with ui.navset_pill(id="selected_navset_pill"):
+    with ui.nav_panel("A"):
+        "Panel A content"
+
+    with ui.nav_panel("B"):
+        "Panel B content"
+
+    with ui.nav_panel("C"):
+        "Panel C content"
+
+    with ui.nav_menu("Other links"):
+        with ui.nav_panel("D"):
+            "Page D content"
+
+        "----"
+        "Description:"
+        with ui.nav_control():
+            ui.a("Shiny", href="https://shiny.posit.co", target="_blank")
+ui.h5("Selected:")
+
+
+@render.code
+def _():
+    return input.selected_navset_pill()
+
+
+with ui.navset_underline(id="selected_navset_underline"):
+    with ui.nav_panel("A"):
+        "Panel A content"
+
+    with ui.nav_panel("B"):
+        "Panel B content"
+
+    with ui.nav_panel("C"):
+        "Panel C content"
+
+    with ui.nav_menu("Other links"):
+        with ui.nav_panel("D"):
+            "Page D content"
+
+        "----"
+        "Description:"
+        with ui.nav_control():
+            ui.a("Shiny", href="https://shiny.posit.co", target="_blank")
+ui.h5("Selected:")
+
+
+@render.code
+def _underline():
+    return input.selected_navset_underline()
diff --git a/tests/playwright/shiny/components/nav/navset_menu/test_app.py b/tests/playwright/shiny/components/nav/navset_menu/test_app.py
new file mode 100644
index 000000000..028374707
--- /dev/null
+++ b/tests/playwright/shiny/components/nav/navset_menu/test_app.py
@@ -0,0 +1,39 @@
+from typing import Union
+
+import pytest
+from playwright.sync_api import Page
+
+from shiny.playwright import controller
+from shiny.pytest import create_app_fixture
+from shiny.run import ShinyAppProc
+
+app = create_app_fixture(["app-express.py"])
+
+
+@pytest.mark.parametrize(
+    "nav_factory,nav_id,out_id",
+    [
+        (controller.NavsetPill, "selected_navset_pill", "_"),
+        (controller.NavsetUnderline, "selected_navset_underline", "_underline"),
+    ],
+    ids=["pill", "underline"],
+)
+def test_navset_menu(
+    page: Page,
+    app: ShinyAppProc,
+    nav_factory: Union[type[controller.NavsetPill], type[controller.NavsetUnderline]],
+    nav_id: str,
+    out_id: str,
+):
+
+    page.goto(app.url)
+    navset = nav_factory(page, nav_id)
+    output: controller.OutputText = controller.OutputText(page, out_id)
+
+    navset.expect_value("A")
+    output.expect_value("A")
+
+    for panel in ["B", "C", "D"]:
+        navset.set(panel)
+        navset.expect_value(panel)
+        output.expect_value(panel)