diff --git a/eclipse-plugins/edu.wpi.first.wpilib.plugins.java/src/main/java/edu/wpi/first/wpilib/plugins/java/launching/JavaLaunchShortcut.java b/eclipse-plugins/edu.wpi.first.wpilib.plugins.java/src/main/java/edu/wpi/first/wpilib/plugins/java/launching/JavaLaunchShortcut.java
index c67daa32b3..481a4638ab 100644
--- a/eclipse-plugins/edu.wpi.first.wpilib.plugins.java/src/main/java/edu/wpi/first/wpilib/plugins/java/launching/JavaLaunchShortcut.java
+++ b/eclipse-plugins/edu.wpi.first.wpilib.plugins.java/src/main/java/edu/wpi/first/wpilib/plugins/java/launching/JavaLaunchShortcut.java
@@ -2,6 +2,7 @@ package edu.wpi.first.wpilib.plugins.java.launching;
 
 import java.io.File;
 import java.lang.reflect.Method;
+import java.text.MessageFormat;
 import java.util.HashMap;
 import java.util.Map;
 import java.util.Vector;
@@ -15,8 +16,6 @@ import org.eclipse.debug.core.ILaunch;
 import org.eclipse.debug.core.ILaunchConfigurationType;
 import org.eclipse.debug.core.ILaunchConfigurationWorkingCopy;
 import org.eclipse.debug.core.ILaunchManager;
-import org.eclipse.debug.core.IStreamListener;
-import org.eclipse.debug.core.model.IStreamMonitor;
 import org.eclipse.debug.ui.IDebugUIConstants;
 import org.eclipse.debug.ui.ILaunchShortcut;
 import org.eclipse.jdt.core.IJavaElement;
@@ -37,13 +36,13 @@ import edu.wpi.first.wpilib.plugins.java.WPILibJavaPlugin;
 
 @SuppressWarnings("restriction")
 public abstract class JavaLaunchShortcut implements ILaunchShortcut {
+	private static final int DEBUG_ATTACH_ATTEMPTS = 20;
+	private static final int DEBUG_ATTACH_RETRY_DELAY_SEC = 2;
+	
 	//Class constants - used to delineate types for launch shortcuts
 	public static final String DEPLOY_TYPE = "edu.wpi.first.wpilib.plugins.core.deploy";
 	private static final String ANT_SERVER_THREAD_NAME = "Ant Build Server Connection";
 	
-	// NOTE: This string must be changed if the port is changed. 
-	private static final String DEBUG_START_TEXT = "Listening for transport dt_socket at address: 8348";
-	
 	private static ILaunch lastDeploy = null;
 	
 	/**
@@ -155,11 +154,9 @@ public abstract class JavaLaunchShortcut implements ILaunchShortcut {
 		lastDeploy = AntLauncher.runAntFile(new File (activeProj.getLocation().toOSString() + File.separator + "build.xml"), targets, null, mode);
 		
 		if((mode.equals(ILaunchManager.DEBUG_MODE))&&(getLaunchType().equals(DEPLOY_TYPE))) {
-			ILaunchConfigurationWorkingCopy config;
 			try {
-				config = getRemoteDebugConfig(activeProj);
-				startDebugConfig(config, lastDeploy);
-			} catch (CoreException e) {
+				startDebugConfig(getRemoteDebugConfig(activeProj));
+			} catch (CoreException | InterruptedException e) {
                 WPILibJavaPlugin.logError("Debug attach failed", e);
 			}
 		}
@@ -190,20 +187,28 @@ public abstract class JavaLaunchShortcut implements ILaunchShortcut {
 		return WPILibCore.getDefault().getTargetIP(proj);
 	}
 
-	private void startDebugConfig(final ILaunchConfigurationWorkingCopy config, ILaunch deploy) throws CoreException {
-		IStreamListener listener = new IStreamListener() {
-			@Override
-			public void streamAppended(String text, IStreamMonitor monitor) {
-				if (text.contains(DEBUG_START_TEXT)) {
-					try {
-						config.launch(ILaunchManager.DEBUG_MODE, null);
-					} catch (CoreException e) {
-                        WPILibJavaPlugin.logError("Error starting debug config..", e);
-					}
-					monitor.removeListener(this);
+	private void startDebugConfig(final ILaunchConfigurationWorkingCopy config) 
+			throws CoreException, InterruptedException {
+		int remainingAttempts = DEBUG_ATTACH_ATTEMPTS;
+		
+		// Retry until success or rethrow of exception on failure
+		while (true) {
+			try {
+				WPILibJavaPlugin.logInfo("Attemping to attach debugger...");
+				config.launch(ILaunchManager.DEBUG_MODE, null);
+				WPILibJavaPlugin.logInfo("Debugger attached.");
+				break;
+			} catch (CoreException e) {
+				if (--remainingAttempts > 0) {
+					String errorMsg = MessageFormat.format("Unable to attach debugger. "
+							+ "{0} attempts remain - waiting {1} second(s) before retrying...", 
+							remainingAttempts, DEBUG_ATTACH_RETRY_DELAY_SEC);
+					WPILibJavaPlugin.logError(errorMsg, null);
+					Thread.sleep(DEBUG_ATTACH_RETRY_DELAY_SEC * 1000);
+				} else {
+					throw e;
 				}
 			}
-		};
-		deploy.getProcesses()[0].getStreamsProxy().getOutputStreamMonitor().addListener(listener);
+		}
 	}
 }