diff --git a/bundles/io.openliberty.tools.eclipse.ui/META-INF/MANIFEST.MF b/bundles/io.openliberty.tools.eclipse.ui/META-INF/MANIFEST.MF
index 31498492..09b6e000 100644
--- a/bundles/io.openliberty.tools.eclipse.ui/META-INF/MANIFEST.MF
+++ b/bundles/io.openliberty.tools.eclipse.ui/META-INF/MANIFEST.MF
@@ -27,6 +27,8 @@ Import-Package: org.eclipse.cdt.launch.ui,
  org.eclipse.debug.core,
  org.eclipse.debug.core.model,
  org.eclipse.debug.core.sourcelookup,
+ org.eclipse.debug.internal.ui,
+ org.eclipse.debug.internal.ui.actions,
  org.eclipse.debug.ui,
  org.eclipse.debug.ui.sourcelookup,
  org.eclipse.jdi,
diff --git a/bundles/io.openliberty.tools.eclipse.ui/plugin.xml b/bundles/io.openliberty.tools.eclipse.ui/plugin.xml
index c6cb7875..0c1921ec 100644
--- a/bundles/io.openliberty.tools.eclipse.ui/plugin.xml
+++ b/bundles/io.openliberty.tools.eclipse.ui/plugin.xml
@@ -713,4 +713,30 @@
             name="Liberty">
       </page>
    </extension>
+   
+   <extension
+         point="org.eclipse.ui.popupMenus">
+         
+         <viewerContribution
+            targetID="org.eclipse.debug.ui.DebugView"
+            id="org.eclipse.debug.ui.debugview.popupMenu">
+
+         <action
+               label="Relaunch Liberty"
+               icon="$nl$/icons/full/elcl16/runlast_co.png"
+               helpContextId="relaunch_action_context"
+               class="io.openliberty.tools.eclipse.debug.LibertyDebugRelaunchActionDelegate"
+               menubarPath="launchGroup"
+               id="io.openliberty.tools.eclipse.debug.popupMenu.relaunch">
+         </action>
+         <action
+               label="Disconnect"
+               icon="$nl$/icons/full/elcl16/runlast_co.png"
+               helpContextId="relaunch_action_context"
+               class="io.openliberty.tools.eclipse.debug.LibertyDebugDisconnectActionDelegate"
+               menubarPath="launchGroup"
+               id="io.openliberty.tools.eclipse.debug.popupMenu.disconnect">
+         </action>
+         </viewerContribution>
+   </extension>
 </plugin>
diff --git a/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/DevModeOperations.java b/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/DevModeOperations.java
index 2817edcf..54387f2d 100644
--- a/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/DevModeOperations.java
+++ b/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/DevModeOperations.java
@@ -104,7 +104,7 @@ public class DevModeOperations {
     /**
      * Handles debug mode processing.
      */
-    private DebugModeHandler debugModeHandler;
+    public DebugModeHandler debugModeHandler;
 
     /**
      * The instance of this class.
diff --git a/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/debug/LibertyDebugDisconnectActionDelegate.java b/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/debug/LibertyDebugDisconnectActionDelegate.java
new file mode 100644
index 00000000..7c81576f
--- /dev/null
+++ b/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/debug/LibertyDebugDisconnectActionDelegate.java
@@ -0,0 +1,24 @@
+package io.openliberty.tools.eclipse.debug;
+
+import java.util.Arrays;
+
+import org.eclipse.debug.core.DebugException;
+import org.eclipse.debug.core.ILaunch;
+import org.eclipse.debug.core.model.IDebugTarget;
+import org.eclipse.debug.internal.ui.DebugUIPlugin;
+import org.eclipse.debug.internal.ui.actions.AbstractDebugActionDelegate;
+
+public class LibertyDebugDisconnectActionDelegate extends AbstractDebugActionDelegate {
+
+    @Override
+    protected void doAction(Object object) throws DebugException {
+
+        ILaunch launch = DebugUIPlugin.getLaunch(object);
+        for (IDebugTarget target : Arrays.asList(launch.getDebugTargets())) {
+            if (target instanceof LibertyDebugTarget) {
+                ((LibertyDebugTarget) target).setRelaunch(false);
+            }
+            target.disconnect();
+        }
+    }
+}
diff --git a/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/debug/LibertyDebugRelaunchActionDelegate.java b/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/debug/LibertyDebugRelaunchActionDelegate.java
new file mode 100644
index 00000000..66093705
--- /dev/null
+++ b/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/debug/LibertyDebugRelaunchActionDelegate.java
@@ -0,0 +1,37 @@
+package io.openliberty.tools.eclipse.debug;
+
+import org.eclipse.core.runtime.CoreException;
+import org.eclipse.debug.core.ILaunch;
+import org.eclipse.debug.internal.ui.DebugUIPlugin;
+import org.eclipse.debug.internal.ui.actions.AbstractDebugActionDelegate;
+
+import io.openliberty.tools.eclipse.DevModeOperations;
+import io.openliberty.tools.eclipse.Project;
+import io.openliberty.tools.eclipse.ui.launch.StartTab;
+
+public class LibertyDebugRelaunchActionDelegate extends AbstractDebugActionDelegate {
+
+    @Override
+    protected void doAction(Object object) {
+        ILaunch launch = DebugUIPlugin.getLaunch(object);
+
+        if (launch != null) {
+            DevModeOperations devModeOps = DevModeOperations.getInstance();
+
+            String projectName = "";
+            try {
+                projectName = launch.getLaunchConfiguration().getAttribute(StartTab.PROJECT_NAME, "");
+            } catch (CoreException e) {
+                // TODO Auto-generated catch block
+                e.printStackTrace();
+            }
+
+            Project project = devModeOps.getProjectModel().getProject(projectName);
+
+            if (!devModeOps.isProjectTerminalTabMarkedClosed(projectName)) {
+                devModeOps.debugModeHandler.startDebugAttacher(project, launch, null, true);
+            }
+
+        }
+    }
+}
diff --git a/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/debug/LibertyDebugTarget.java b/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/debug/LibertyDebugTarget.java
index aeb964ba..510b0ecd 100644
--- a/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/debug/LibertyDebugTarget.java
+++ b/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/debug/LibertyDebugTarget.java
@@ -16,11 +16,18 @@
 public class LibertyDebugTarget extends JDIDebugTarget {
 
     private RestartDebugger restartDebugger;
+    private boolean relaunch;
 
     public LibertyDebugTarget(ILaunch launch, VirtualMachine jvm, String name, RestartDebugger restartDebugger) {
         super(launch, jvm, "Liberty Application Debug: " + name, true, true, null, true);
 
         this.restartDebugger = restartDebugger;
+        this.relaunch = true;
+
+    }
+
+    public void setRelaunch(boolean relaunch) {
+        this.relaunch = relaunch;
     }
 
     @Override
@@ -44,9 +51,28 @@ protected void disconnected() {
             cleanup();
 
             getLaunch().removeDebugTarget(this);
-            restartDebugger.restart();
-            restartDebugger = null;
+
+            // Attempt to restart the debugger
+            if (relaunch) {
+                restartDebugger.restart();
+                restartDebugger = null;
+            }
         }
     }
 
+    // @Override
+    // public void disconnect() throws DebugException {
+    // // If we got here, the user explicitly called "disconnect" on the debugger.
+    // // We should not try to reconnect in this case but we should allow the user
+    // // to select "relaunch" which should just reconnect the debugger.
+    // // Since we cant differentiate between a normal "launch" and a "relaunch",
+    // // we will set a flag that we will use to determine if we should launch devMode
+    // // or just reconnect the debugger.
+    // restartDebugger = null;
+    // relaunch = true;
+    //
+    // super.disconnect();
+    //
+    // }
+
 }
diff --git a/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/ui/launch/LaunchConfigurationDelegateLauncher.java b/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/ui/launch/LaunchConfigurationDelegateLauncher.java
index 4fb2f7b6..68d2f54a 100644
--- a/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/ui/launch/LaunchConfigurationDelegateLauncher.java
+++ b/bundles/io.openliberty.tools.eclipse.ui/src/io/openliberty/tools/eclipse/ui/launch/LaunchConfigurationDelegateLauncher.java
@@ -70,6 +70,8 @@ public void launch(ILaunchConfiguration configuration, String mode, ILaunch laun
         IWorkbench workbench = PlatformUI.getWorkbench();
         Display display = workbench.getDisplay();
 
+        // if (launch ==)
+
         // Launch dev mode.
         display.syncExec(new Runnable() {
             public void run() {