diff --git a/bundles/org.eclipse.ui.workbench.texteditor/src/org/eclipse/ui/internal/findandreplace/overlay/FindReplaceOverlay.java b/bundles/org.eclipse.ui.workbench.texteditor/src/org/eclipse/ui/internal/findandreplace/overlay/FindReplaceOverlay.java
index ac389fd96a6..f5638e46464 100644
--- a/bundles/org.eclipse.ui.workbench.texteditor/src/org/eclipse/ui/internal/findandreplace/overlay/FindReplaceOverlay.java
+++ b/bundles/org.eclipse.ui.workbench.texteditor/src/org/eclipse/ui/internal/findandreplace/overlay/FindReplaceOverlay.java
@@ -701,8 +701,8 @@ private void createSearchBar() {
 		searchBar.forceFocus();
 		searchBar.selectAll();
 		searchBar.addModifyListener(e -> {
-			wholeWordSearchButton.setEnabled(findReplaceLogic.isAvailable(SearchOptions.WHOLE_WORD));
 			updateIncrementalSearch();
+			wholeWordSearchButton.setEnabled(findReplaceLogic.isAvailable(SearchOptions.WHOLE_WORD));
 			decorate();
 		});
 		searchBar.addFocusListener(new FocusListener() {
diff --git a/tests/org.eclipse.ui.workbench.texteditor.tests/src/org/eclipse/ui/internal/findandreplace/overlay/FindReplaceOverlayTest.java b/tests/org.eclipse.ui.workbench.texteditor.tests/src/org/eclipse/ui/internal/findandreplace/overlay/FindReplaceOverlayTest.java
index e74eb92d3b4..ddc82604ccc 100644
--- a/tests/org.eclipse.ui.workbench.texteditor.tests/src/org/eclipse/ui/internal/findandreplace/overlay/FindReplaceOverlayTest.java
+++ b/tests/org.eclipse.ui.workbench.texteditor.tests/src/org/eclipse/ui/internal/findandreplace/overlay/FindReplaceOverlayTest.java
@@ -201,6 +201,18 @@ public void testSearchTermStoredInHistoryAfterSearchForward() {
 		assertEquals("foo", dialog.getFindText());
 	}
 
+	@Test
+	public void testWholeWordButtonEnabledStateImmediatelyReflectsCurrentSearchTerm() {
+		initializeTextViewerWithFindReplaceUI("foo bar foo");
+		OverlayAccess dialog= getDialog();
+
+		dialog.setFindText("foo ");
+		dialog.assertDisabled(SearchOptions.WHOLE_WORD);
+
+		dialog.setFindText("foo");
+		dialog.assertEnabled(SearchOptions.WHOLE_WORD);
+	}
+
 	@Test
 	public void testSearchTermStoredInHistoryAfterSearchBackward() {
 		// Backward search must persist the term to history just like forward search.