diff --git a/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/actions/expressions/WatchHandler.java b/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/actions/expressions/WatchHandler.java
index a45587081a2..a546cb07c71 100644
--- a/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/actions/expressions/WatchHandler.java
+++ b/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/actions/expressions/WatchHandler.java
@@ -1,5 +1,5 @@
 /*******************************************************************************
- * Copyright (c) 2008, 2015 Wind River Systems and others.
+ * Copyright (c) 2008, 2025 Wind River Systems and others.
  *
  * This program and the accompanying materials
  * are made available under the terms of the Eclipse Public License 2.0
@@ -10,16 +10,16 @@
  *
  * Contributors:
  *     Wind River Systems - initial API and implementation
+ *     IBM Corporation - Improved expression creation
  *******************************************************************************/
 package org.eclipse.debug.internal.ui.actions.expressions;
 
-import java.util.Iterator;
-
 import org.eclipse.core.commands.AbstractHandler;
 import org.eclipse.core.commands.ExecutionEvent;
 import org.eclipse.core.commands.ExecutionException;
 import org.eclipse.core.runtime.CoreException;
 import org.eclipse.core.runtime.IAdaptable;
+import org.eclipse.debug.core.DebugException;
 import org.eclipse.debug.core.DebugPlugin;
 import org.eclipse.debug.core.ILaunch;
 import org.eclipse.debug.core.model.IDebugElement;
@@ -32,7 +32,8 @@
 import org.eclipse.debug.ui.actions.IWatchExpressionFactoryAdapter;
 import org.eclipse.debug.ui.actions.IWatchExpressionFactoryAdapter2;
 import org.eclipse.jface.viewers.ISelection;
-import org.eclipse.jface.viewers.IStructuredSelection;
+import org.eclipse.jface.viewers.TreePath;
+import org.eclipse.jface.viewers.TreeSelection;
 import org.eclipse.ui.IViewPart;
 import org.eclipse.ui.IWorkbenchPage;
 import org.eclipse.ui.PartInitException;
@@ -49,11 +50,26 @@ public class WatchHandler extends AbstractHandler {
 	@Override
 	public Object execute(ExecutionEvent event) throws ExecutionException {
 		ISelection selection = HandlerUtil.getCurrentSelection(event);
-		if (selection instanceof IStructuredSelection) {
-			Iterator<?> iter = ((IStructuredSelection)selection).iterator();
-			while (iter.hasNext()) {
-				Object element = iter.next();
-				createExpression(element);
+		if (selection instanceof TreeSelection treeSelection) {
+			for (TreePath path : treeSelection.getPaths()) {
+				if (path.getSegmentCount() > 1) {
+					StringBuilder expressionString = new StringBuilder();
+					for (int e = 0; e < path.getSegmentCount(); e++) {
+						IVariable variable = (IVariable) path.getSegment(e);
+						try {
+							expressionString.append(variable.getName());
+							expressionString.append("."); //$NON-NLS-1$
+						} catch (DebugException e1) {
+							DebugUIPlugin.log(e1);
+						}
+					}
+					expressionString.deleteCharAt(expressionString.length() - 1);
+					createWatchExpression(expressionString.toString());
+				} else {
+					Object element = path.getFirstSegment();
+					createExpression(element);
+				}
+				showExpressionsView();
 			}
 		}
 		return null;
@@ -96,9 +112,13 @@ private void createExpression(Object element) {
 			DebugUIPlugin.errorDialog(DebugUIPlugin.getShell(), ActionMessages.WatchAction_0, ActionMessages.WatchAction_1, e); //
 			return;
 		}
+		createWatchExpression(expressionString);
+		showExpressionsView();
+	}
 
+	private void createWatchExpression(String expressionString) {
 		IWatchExpression expression;
-			expression = DebugPlugin.getDefault().getExpressionManager().newWatchExpression(expressionString);
+		expression = DebugPlugin.getDefault().getExpressionManager().newWatchExpression(expressionString);
 		DebugPlugin.getDefault().getExpressionManager().addExpression(expression);
 		IAdaptable object = DebugUITools.getDebugContext();
 		IDebugElement context = null;
@@ -108,10 +128,8 @@ private void createExpression(Object element) {
 			context = ((ILaunch) object).getDebugTarget();
 		}
 		expression.setExpressionContext(context);
-		showExpressionsView();
 	}
 
-
 	/**
 	 * Returns the factory adapter for the given variable or <code>null</code> if none.
 	 *
diff --git a/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/views/expression/ExpressionDropAdapter.java b/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/views/expression/ExpressionDropAdapter.java
index 7df7c13b770..032bcf97edc 100644
--- a/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/views/expression/ExpressionDropAdapter.java
+++ b/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/views/expression/ExpressionDropAdapter.java
@@ -1,5 +1,5 @@
 /*******************************************************************************
- * Copyright (c) 2007, 2013 IBM Corporation and others.
+ * Copyright (c) 2007, 2025 IBM Corporation and others.
  *
  * This program and the accompanying materials
  * are made available under the terms of the Eclipse Public License 2.0
@@ -23,6 +23,7 @@
 import org.eclipse.core.runtime.IAdaptable;
 import org.eclipse.core.runtime.IStatus;
 import org.eclipse.core.runtime.Status;
+import org.eclipse.debug.core.DebugException;
 import org.eclipse.debug.core.DebugPlugin;
 import org.eclipse.debug.core.IExpressionManager;
 import org.eclipse.debug.core.ILaunch;
@@ -40,6 +41,8 @@
 import org.eclipse.debug.ui.actions.IWatchExpressionFactoryAdapterExtension;
 import org.eclipse.jface.util.LocalSelectionTransfer;
 import org.eclipse.jface.viewers.IStructuredSelection;
+import org.eclipse.jface.viewers.TreePath;
+import org.eclipse.jface.viewers.TreeSelection;
 import org.eclipse.jface.viewers.ViewerDropAdapter;
 import org.eclipse.swt.dnd.DND;
 import org.eclipse.swt.dnd.DropTargetEvent;
@@ -373,19 +376,28 @@ private boolean performExpressionDrop(IStructuredSelection selection) {
 	 */
 	private boolean performVariableOrWatchAdaptableDrop(IStructuredSelection selection) {
 		List<IExpression> expressions = new ArrayList<>(selection.size());
-		for (Iterator<?> itr = selection.iterator(); itr.hasNext();) {
-			Object element = itr.next();
-			String expressionText = createExpressionString(element);
-			if (expressionText != null){
-				IExpression expression = createExpression(expressionText);
-				if (expression != null){
-					expressions.add(expression);
+		IExpression expression;
+		if (selection instanceof TreeSelection treeSelection) {
+			for (TreePath path : treeSelection.getPaths()) {
+				if (path.getSegmentCount() > 1) {
+					StringBuilder expressionString = new StringBuilder();
+					for (int e = 0; e < path.getSegmentCount(); e++) {
+						IVariable variable = (IVariable) path.getSegment(e);
+						try {
+							expressionString.append(variable.getName());
+							expressionString.append("."); //$NON-NLS-1$
+						} catch (DebugException e1) {
+							DebugUIPlugin.log(e1);
+						}
+					}
+					expressionString.deleteCharAt(expressionString.length() - 1);
+					expression = createExpression(expressionString.toString());
 				} else {
-					DebugUIPlugin.log(new Status(IStatus.ERROR,DebugUIPlugin.getUniqueIdentifier(),"Drop failed.  Watch expression could not be created for the text " + expressionText)); //$NON-NLS-1$
-					return false;
+					Object element = path.getFirstSegment();
+					String expressionText = createExpressionString(element);
+					expression = createExpression(expressionText);
 				}
-			} else {
-				return false;
+				expressions.add(expression);
 			}
 		}
 		if (expressions.size() == selection.size()){