diff --git a/debug/org.eclipse.debug.core/core/org/eclipse/debug/core/Launch.java b/debug/org.eclipse.debug.core/core/org/eclipse/debug/core/Launch.java
index ad366baf37a..69b85321233 100644
--- a/debug/org.eclipse.debug.core/core/org/eclipse/debug/core/Launch.java
+++ b/debug/org.eclipse.debug.core/core/org/eclipse/debug/core/Launch.java
@@ -1,5 +1,5 @@
 /*******************************************************************************
- * Copyright (c) 2000, 2018 IBM Corporation and others.
+ * Copyright (c) 2000, 2026 IBM Corporation and others.
  *
  * This program and the accompanying materials
  * are made available under the terms of the Eclipse Public License 2.0
@@ -25,6 +25,7 @@
 import java.util.concurrent.locks.ReadWriteLock;
 import java.util.concurrent.locks.ReentrantReadWriteLock;
 
+import org.eclipse.core.runtime.CoreException;
 import org.eclipse.core.runtime.IStatus;
 import org.eclipse.core.runtime.MultiStatus;
 import org.eclipse.core.runtime.PlatformObject;
@@ -475,7 +476,18 @@ protected void fireChanged() {
 	 * properly created/initialized.
 	 */
 	protected void fireTerminate() {
-		setAttribute(DebugPlugin.ATTR_TERMINATE_TIMESTAMP, Long.toString(System.currentTimeMillis()));
+		String timeStamp = Long.toString(System.currentTimeMillis());
+		setAttribute(DebugPlugin.ATTR_TERMINATE_TIMESTAMP, timeStamp);
+		ILaunchConfiguration launchConfig = getLaunchConfiguration();
+		if (launchConfig != null) {
+			try {
+				ILaunchConfigurationWorkingCopy launchCopy = getLaunchConfiguration().getWorkingCopy();
+				launchCopy.setAttribute(DebugPlugin.ATTR_TERMINATE_TIMESTAMP, timeStamp);
+				launchCopy.doSave();
+			} catch (CoreException e) {
+				DebugPlugin.log(e);
+			}
+		}
 		if (!fSuppressChange) {
 			((LaunchManager)getLaunchManager()).fireUpdate(this, LaunchManager.TERMINATE);
 			((LaunchManager)getLaunchManager()).fireUpdate(new ILaunch[] {this}, LaunchManager.TERMINATE);
diff --git a/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/actions/ActionMessages.java b/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/actions/ActionMessages.java
index 606467dee19..8942b51694a 100644
--- a/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/actions/ActionMessages.java
+++ b/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/actions/ActionMessages.java
@@ -261,5 +261,12 @@ public class ActionMessages extends NLS {
 	public static String ExpressionPasteDialog;
 	public static String ExpressionPasteRemember;
 	public static String ExpressionPastePromptButton;
+	public static String LaunchActionToolTip_Seconds;
+	public static String LaunchActionToolTip_Minutes;
+	public static String LaunchActionToolTip_OneMinute;
+	public static String LaunchActionToolTip_OneHour;
+	public static String LaunchActionToolTip_Hours;
+	public static String LaunchActionToolTip_OneDay;
+	public static String LaunchActionToolTip_Days;
 
 }
\ No newline at end of file
diff --git a/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/actions/ActionMessages.properties b/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/actions/ActionMessages.properties
index 24c158b608b..e16e1bb711c 100644
--- a/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/actions/ActionMessages.properties
+++ b/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/internal/ui/actions/ActionMessages.properties
@@ -245,4 +245,15 @@ ExpressionPasteSingleButton=Single Expression
 ExpressionPastePromptButton=Prompt
 ExpressionPasteTitle=Paste Multiline Expression
 ExpressionPasteDialog=You are pasting a multiline expression. Choose whether to paste it as a single combined expression or as separate multiple expressions.
-ExpressionPasteRemember=Remember my preference next time
\ No newline at end of file
+ExpressionPasteRemember=Remember my preference next time
+
+LaunchActionToolTip_Seconds = a moment ago
+LaunchActionToolTip_OneMinute = 1 min ago
+LaunchActionToolTip_Minutes = {0} mins ago
+LaunchActionToolTip_OneHour = 1 hour ago
+LaunchActionToolTip_Hours = {0} hours ago
+LaunchActionToolTip_OneDay = 1 day ago
+LaunchActionToolTip_Days = {0} days ago
+
+
+
diff --git a/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/ui/actions/AbstractLaunchHistoryAction.java b/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/ui/actions/AbstractLaunchHistoryAction.java
index 0a5d52c57b8..813f8c096f6 100644
--- a/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/ui/actions/AbstractLaunchHistoryAction.java
+++ b/debug/org.eclipse.debug.ui/ui/org/eclipse/debug/ui/actions/AbstractLaunchHistoryAction.java
@@ -1,5 +1,5 @@
 /*******************************************************************************
- * Copyright (c) 2000, 2016 IBM Corporation and others.
+ * Copyright (c) 2000, 2026 IBM Corporation and others.
  *
  * This program and the accompanying materials
  * are made available under the terms of the Eclipse Public License 2.0
@@ -50,6 +50,7 @@
 import org.eclipse.jface.viewers.ISelection;
 import org.eclipse.jface.viewers.IStructuredSelection;
 import org.eclipse.jface.viewers.StructuredSelection;
+import org.eclipse.osgi.util.NLS;
 import org.eclipse.swt.SWT;
 import org.eclipse.swt.events.MenuAdapter;
 import org.eclipse.swt.events.MenuEvent;
@@ -353,6 +354,8 @@ protected void fillMenu(Menu menu) {
 			LaunchAction action= new LaunchAction(launch, getMode());
 			if (checkIfLaunchActive(launch, launches)) {
 				action.setText(action.getText() + "  \u2699"); //$NON-NLS-1$
+			} else {
+				addRecentLaunchTimeTooltip(launch, action);
 			}
 			addToMenu(menu, action, accelerator);
 			accelerator++;
@@ -368,7 +371,10 @@ protected void fillMenu(Menu menu) {
 			LaunchAction action= new LaunchAction(launch, getMode());
 			if (checkIfLaunchActive(launch, launches)) {
 				action.setText(action.getText() + "  \u2699"); //$NON-NLS-1$
+			} else {
+				addRecentLaunchTimeTooltip(launch, action);
 			}
+			addRecentLaunchTimeTooltip(launch, action);
 			addToMenu(menu, action, accelerator);
 			accelerator++;
 		}
@@ -627,4 +633,65 @@ private LaunchConfigurationManager getLaunchConfigurationManager() {
 	protected String getLaunchGroupIdentifier() {
 		return fLaunchGroup.getIdentifier();
 	}
+
+	/**
+	 * Adds a tooltip showing how long ago the given launch was terminated if
+	 * there's a valid terminate timestamp attribute.
+	 *
+	 * @param launch       launch configuration
+	 * @param launchAction launch action to update
+	 */
+	private void addRecentLaunchTimeTooltip(ILaunchConfiguration launch, LaunchAction launchAction) {
+		try {
+			String timeStamp = launch.getAttribute(DebugPlugin.ATTR_TERMINATE_TIMESTAMP, ""); //$NON-NLS-1$
+			if (!timeStamp.isEmpty()) {
+				long mytime = Long.parseLong(timeStamp);
+				String g = getRelativeTime(mytime);
+				launchAction.setToolTipText(g);
+			}
+		} catch (CoreException e) {
+			DebugUIPlugin.log(e);
+		}
+	}
+
+	/**
+	 * Returns a human-readable relative time string for the given timestamp.
+	 *
+	 * @param timestamp timestamp in milliseconds since the epoch
+	 * @return relative time string
+	 */
+	private String getRelativeTime(long timestamp) {
+		long diffMillis = System.currentTimeMillis() - timestamp;
+		long seconds = diffMillis / 1000;
+
+		if (seconds < 60) {
+			return ActionMessages.LaunchActionToolTip_Seconds;
+		}
+
+		long minutes = seconds / 60;
+
+		if (minutes == 1) {
+			return ActionMessages.LaunchActionToolTip_OneMinute;
+		}
+		if (minutes < 60) {
+			return NLS.bind(ActionMessages.LaunchActionToolTip_Minutes, minutes);
+		}
+
+		long hours = minutes / 60;
+
+		if (hours == 1) {
+			return ActionMessages.LaunchActionToolTip_OneHour;
+		}
+		if (hours < 24) {
+			return NLS.bind(ActionMessages.LaunchActionToolTip_Hours, hours);
+		}
+
+		long days = hours / 24;
+
+		if (days == 1) {
+			return ActionMessages.LaunchActionToolTip_OneDay;
+		}
+		return NLS.bind(ActionMessages.LaunchActionToolTip_Days, days);
+	}
+
 }