diff --git a/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/ShowInMenu.java b/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/ShowInMenu.java
index 81068c7bd0d..fd108657560 100644
--- a/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/ShowInMenu.java
+++ b/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/ShowInMenu.java
@@ -27,6 +27,7 @@
 import org.eclipse.e4.ui.model.application.MApplication;
 import org.eclipse.e4.ui.model.application.commands.MCommand;
 import org.eclipse.e4.ui.model.application.commands.MParameter;
+import org.eclipse.e4.ui.model.application.ui.MExpression;
 import org.eclipse.e4.ui.model.application.ui.menu.MHandledMenuItem;
 import org.eclipse.e4.ui.model.application.ui.menu.MMenu;
 import org.eclipse.e4.ui.model.application.ui.menu.MMenuContribution;
@@ -247,7 +248,12 @@ private void fillMenu(IMenuManager innerMgr) {
 							ccip.parameters.put(menuParam.getName(), menuParam.getValue());
 						}
 					}
-					innerMgr.add(new CommandContributionItem(ccip));
+					CommandContributionItem cci = new CommandContributionItem(ccip);
+					MExpression visibleWhen = menuElement.getVisibleWhen();
+					if (visibleWhen != null) {
+						cci.setVisible(ContributionsAnalyzer.isVisible(visibleWhen, eContext));
+					}
+					innerMgr.add(cci);
 				}
 			}
 		}
diff --git a/tests/org.eclipse.ui.tests/Eclipse UI Tests/org/eclipse/ui/tests/menus/MenusTestSuite.java b/tests/org.eclipse.ui.tests/Eclipse UI Tests/org/eclipse/ui/tests/menus/MenusTestSuite.java
index 5c20967891f..d72e325e101 100644
--- a/tests/org.eclipse.ui.tests/Eclipse UI Tests/org/eclipse/ui/tests/menus/MenusTestSuite.java	
+++ b/tests/org.eclipse.ui.tests/Eclipse UI Tests/org/eclipse/ui/tests/menus/MenusTestSuite.java	
@@ -31,6 +31,7 @@
 		DynamicMenuTest.class,
 		Bug231304Test.class,
 		ShowViewMenuTest.class,
+		ShowInMenuTest.class,
 		Bug264804Test.class,
 		MenuHelperTest.class,
 		Bug410426Test.class,
diff --git a/tests/org.eclipse.ui.tests/Eclipse UI Tests/org/eclipse/ui/tests/menus/ShowInMenuTest.java b/tests/org.eclipse.ui.tests/Eclipse UI Tests/org/eclipse/ui/tests/menus/ShowInMenuTest.java
new file mode 100644
index 00000000000..3a3c308fa37
--- /dev/null
+++ b/tests/org.eclipse.ui.tests/Eclipse UI Tests/org/eclipse/ui/tests/menus/ShowInMenuTest.java	
@@ -0,0 +1,108 @@
+package org.eclipse.ui.tests.menus;
+
+import static org.eclipse.ui.tests.harness.util.UITestUtil.openTestWindow;
+import static org.junit.Assert.assertNotNull;
+import static org.junit.Assert.assertNull;
+
+import java.util.List;
+
+import org.eclipse.core.resources.IProject;
+import org.eclipse.core.runtime.CoreException;
+import org.eclipse.jface.action.ContributionItem;
+import org.eclipse.jface.action.IContributionItem;
+import org.eclipse.jface.viewers.ISelectionProvider;
+import org.eclipse.jface.viewers.StructuredSelection;
+import org.eclipse.swt.widgets.Menu;
+import org.eclipse.swt.widgets.MenuItem;
+import org.eclipse.ui.IPageLayout;
+import org.eclipse.ui.IViewPart;
+import org.eclipse.ui.IWorkbenchPage;
+import org.eclipse.ui.IWorkbenchWindow;
+import org.eclipse.ui.actions.ContributionItemFactory;
+import org.eclipse.ui.ide.IDE;
+import org.eclipse.ui.internal.ide.handlers.ShowInSystemExplorerHandler;
+import org.eclipse.ui.tests.harness.util.CloseTestWindowsExtension;
+import org.eclipse.ui.tests.harness.util.EditorTestHelper;
+import org.eclipse.ui.tests.harness.util.FileUtil;
+import org.junit.jupiter.api.AfterEach;
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.ExtendWith;
+
+@ExtendWith(CloseTestWindowsExtension.class)
+public class ShowInMenuTest {
+
+	private static final String TEST_ITEM_ID = "org.eclipse.ui.tests.menus.showInMenuTestItem";
+
+	private IWorkbenchWindow window;
+	private IWorkbenchPage page;
+	private List<IProject> projects;
+
+	@BeforeEach
+	public final void setUp() throws Exception {
+		window = openTestWindow(IDE.RESOURCE_PERSPECTIVE_ID);
+		page = window.getActivePage();
+		projects = List.of(FileUtil.createProject("a"), FileUtil.createProject("b"));
+	}
+
+	@AfterEach
+	public final void tearDown() throws Exception {
+		for (IProject project : projects) {
+			FileUtil.deleteProject(project);
+		}
+	}
+
+	@Test
+	void testVisibleWhenEvaluation() throws CoreException {
+		IViewPart viewPart = page.showView(IPageLayout.ID_PROJECT_EXPLORER);
+		ISelectionProvider selectionProvider = viewPart.getSite().getSelectionProvider();
+		IWorkbenchWindow workbenchWindow = EditorTestHelper.getActiveWorkbenchWindow();
+
+		// Test item should be visible when selecting a single project
+		selectionProvider.setSelection(new StructuredSelection(projects.get(0)));
+		Menu menu = computeShowInMenu(workbenchWindow);
+
+		assertNotNull(getContributionItemById(menu, TEST_ITEM_ID));
+
+		// Test item should be hidden when selecting multiple projects
+		selectionProvider.setSelection(new StructuredSelection(projects));
+		menu = computeShowInMenu(workbenchWindow);
+
+		assertNull(getContributionItemById(menu, TEST_ITEM_ID));
+	}
+
+	@Test
+	void testVisibleWhenEvaluationForShowInSystemExplorer() throws CoreException {
+		IViewPart viewPart = page.showView(IPageLayout.ID_PROJECT_EXPLORER);
+		ISelectionProvider selectionProvider = viewPart.getSite().getSelectionProvider();
+		IWorkbenchWindow workbenchWindow = EditorTestHelper.getActiveWorkbenchWindow();
+
+		// "Show in System Explorer" should be visible when selecting a single project
+		selectionProvider.setSelection(new StructuredSelection(projects.get(0)));
+		Menu menu = computeShowInMenu(workbenchWindow);
+
+		assertNotNull(getContributionItemById(menu, ShowInSystemExplorerHandler.ID));
+
+		// "Show in System Explorer" should be hidden when selecting multiple projects
+		selectionProvider.setSelection(new StructuredSelection(projects));
+		menu = computeShowInMenu(workbenchWindow);
+
+		assertNull(getContributionItemById(menu, ShowInSystemExplorerHandler.ID));
+	}
+
+	private static Menu computeShowInMenu(IWorkbenchWindow workbenchWindow) {
+		IContributionItem contributionItem = ContributionItemFactory.VIEWS_SHOW_IN.create(workbenchWindow);
+		Menu menu = new Menu(workbenchWindow.getShell());
+		contributionItem.fill(menu, 0);
+		return menu;
+	}
+
+	private static ContributionItem getContributionItemById(Menu menu, String id) {
+		for (MenuItem item : menu.getItems()) {
+			if (item.getData() instanceof ContributionItem contributionItem && contributionItem.getId().equals(id)) {
+				return contributionItem;
+			}
+		}
+		return null;
+	}
+}
diff --git a/tests/org.eclipse.ui.tests/plugin.xml b/tests/org.eclipse.ui.tests/plugin.xml
index ff0e00b74cc..eb2e3396754 100644
--- a/tests/org.eclipse.ui.tests/plugin.xml
+++ b/tests/org.eclipse.ui.tests/plugin.xml
@@ -3911,6 +3911,24 @@
                style="push">
          </command>
       </menuContribution>
+      <menuContribution
+            allPopups="false"
+            locationURI="popup:org.eclipse.ui.menus.showInMenu">
+         <command
+               commandId="org.eclipse.ui.tests.menus.showInMenuTestItem"
+               label="Show In Menu Test Item"
+               style="push">
+            <visibleWhen
+                  checkEnabled="false">
+               <with
+                     variable="selection">
+                  <count
+                        value="1">
+                  </count>
+               </with>
+            </visibleWhen>
+         </command>
+      </menuContribution>
    </extension>
    <extension
          point="org.eclipse.ui.contexts">