diff --git a/java/src/processing/mode/java/Debugger.java b/java/src/processing/mode/java/Debugger.java
index 5d7eecb57..ac6835b21 100644
--- a/java/src/processing/mode/java/Debugger.java
+++ b/java/src/processing/mode/java/Debugger.java
@@ -29,6 +29,7 @@ import java.util.ArrayList;
 import java.util.HashMap;
 import java.util.HashSet;
 import java.util.Iterator;
+import java.util.LinkedHashSet;
 import java.util.List;
 import java.util.Map;
 import java.util.Map.Entry;
@@ -68,7 +69,7 @@ public class Debugger {
   protected ReferenceType mainClass;
 
   /// holds all loaded classes in the debuggee VM
-  protected Set<ReferenceType> classes = new HashSet<>();
+  protected Set<ReferenceType> classes = new LinkedHashSet<>();
 
   /// listeners for class load events
   protected List<ClassLoadListener> classLoadListeners = new ArrayList<>();
@@ -124,24 +125,12 @@ public class Debugger {
 
 
   /**
-   * Get the {@link ReferenceType} for a class name.
-   * @param name the class name
-   * @return the {@link ReferenceType} or null if not found
-   * (e.g. not yet loaded)
+   * Get the main and nested {@link ReferenceType}s for the sketch.
+   * @return a list of main and nested {@link ReferenceType}s,
+   * empty list if nothing found (e.g. not yet loaded)
    */
-  public ReferenceType getClass(String name) {
-    if (name == null) {
-      return null;
-    }
-    if (name.equals(mainClassName)) {
-      return mainClass;
-    }
-    for (ReferenceType rt : classes) {
-      if (rt.name().equals(name)) {
-        return rt;
-      }
-    }
-    return null;
+  public Set<ReferenceType> getClasses() {
+    return classes;
   }
 
 
@@ -239,6 +228,11 @@ public class Debugger {
     editor.variableInspector().lock();
     if (runtime != null) {
       Messages.log("closing runtime");
+
+      for (LineBreakpoint bp : breakpoints) {
+        bp.detach();
+      }
+
       runtime.close();
       runtime = null;
       //build = null;
@@ -563,21 +557,25 @@ public class Debugger {
     }
   }
 
+  private void createClassPrepareRequest(String name) {
+    ClassPrepareRequest classPrepareRequest = runtime.vm().eventRequestManager().createClassPrepareRequest();
+    classPrepareRequest.addClassFilter(name);
+    classPrepareRequest.enable();
+  }
+
 
   private void vmStartEvent() {
     // break on main class load
     log("requesting event on main class load: " + mainClassName);
-    ClassPrepareRequest mainClassPrepare = runtime.vm().eventRequestManager().createClassPrepareRequest();
-    mainClassPrepare.addClassFilter(mainClassName);
-    mainClassPrepare.enable();
-
+    createClassPrepareRequest(mainClassName);
+    createClassPrepareRequest(mainClassName + "$*");
     // break on loading custom classes
     for (SketchCode tab : editor.getSketch().getCode()) {
       if (tab.isExtension("java")) {
         log("requesting event on class load: " + tab.getPrettyName());
-        ClassPrepareRequest customClassPrepare = runtime.vm().eventRequestManager().createClassPrepareRequest();
-        customClassPrepare.addClassFilter(tab.getPrettyName());
-        customClassPrepare.enable();
+        String name = tab.getPrettyName();
+        createClassPrepareRequest(name);
+        createClassPrepareRequest(name + "$*");
       }
     }
     runtime.vm().resume();
@@ -592,6 +590,7 @@ public class Debugger {
     if (rt.name().equals(mainClassName)) {
       //printType(rt);
       mainClass = rt;
+      classes.add(rt);
       log("main class load: " + rt.name());
       started = true; // now that main class is loaded, we're started
     } else {
diff --git a/java/src/processing/mode/java/debug/LineBreakpoint.java b/java/src/processing/mode/java/debug/LineBreakpoint.java
index 584b780a3..e5743707b 100644
--- a/java/src/processing/mode/java/debug/LineBreakpoint.java
+++ b/java/src/processing/mode/java/debug/LineBreakpoint.java
@@ -29,6 +29,7 @@ import processing.mode.java.Debugger;
 import com.sun.jdi.AbsentInformationException;
 import com.sun.jdi.Location;
 import com.sun.jdi.ReferenceType;
+import com.sun.jdi.VMDisconnectedException;
 import com.sun.jdi.request.BreakpointRequest;
 
 
@@ -40,7 +41,7 @@ public class LineBreakpoint implements ClassLoadListener {
   protected Debugger dbg; // the debugger
   protected LineID line; // the line this breakpoint is set on
   protected BreakpointRequest bpr; // the request on the VM's event request manager
-  protected ReferenceType theClass; // the class containing this breakpoint, null when not yet loaded
+  protected String className;
 
 
   /**
@@ -56,9 +57,9 @@ public class LineBreakpoint implements ClassLoadListener {
     this.line = line;
     line.startTracking(dbg.getEditor().getTab(line.fileName()).getDocument());
     this.dbg = dbg;
-    theClass = dbg.getClass(className()); // try to get the class immediately, may return null if not yet loaded
+    this.className = className();
     set(); // activate the breakpoint (show highlight, attach if debugger is running)
-    Messages.log("LBP Created " + toString() + " class: " + className());
+    Messages.log("LBP Created " + toString() + " class: " + this.className);
   }
 
 
@@ -94,48 +95,61 @@ public class LineBreakpoint implements ClassLoadListener {
   /**
    * Attach this breakpoint to the VM. Creates and enables a
    * {@link BreakpointRequest}. VM needs to be paused.
+   *
+   * @param theClass class to attach to
+   * @return true on success
    */
-  protected void attach() {
-    if (!dbg.isPaused()) {
-      log("can't attach breakpoint, debugger not paused");
-      return;
+  protected boolean attach(ReferenceType theClass) {
+
+    if (theClass == null || className == null ||
+        !className.equals(parseTopLevelClassName(theClass.name()))) {
+      return false;
     }
 
-    if (theClass == null) {
-      log("can't attach breakpoint, class not loaded: " + className());
-      return;
+    log("trying to attach: " + line.fileName + ":" + line.lineIdx + " to " + theClass.name());
+
+    if (!dbg.isPaused()) {
+      log("can't attach breakpoint, debugger not paused");
+      return false;
     }
 
     // find line in java space
     LineID javaLine = dbg.sketchToJavaLine(line);
     if (javaLine == null) {
       log("couldn't find line " + line + " in the java code");
-      return;
+      return false;
     }
     try {
       log("BPs of class: " + theClass + ", line " + (javaLine.lineIdx() + 1));
       List<Location> locations = theClass.locationsOfLine(javaLine.lineIdx() + 1);
       if (locations.isEmpty()) {
         log("no location found for line " + line + " -> " + javaLine);
-        return;
+        return false;
       }
       // use first found location
       bpr = dbg.vm().eventRequestManager().createBreakpointRequest(locations.get(0));
       bpr.enable();
       log("attached breakpoint to " + line + " -> " + javaLine);
+      return true;
     } catch (AbsentInformationException ex) {
       Messages.loge(null, ex);
     }
+    return false;
   }
 
+  protected boolean isAttached() {
+    return bpr != null;
+  }
 
   /**
    * Detach this breakpoint from the VM. Deletes the
    * {@link BreakpointRequest}.
    */
-  protected void detach() {
+  public void detach() {
     if (bpr != null) {
-      dbg.vm().eventRequestManager().deleteEventRequest(bpr);
+      try {
+        dbg.vm().eventRequestManager().deleteEventRequest(bpr);
+      } catch (VMDisconnectedException ignore) { }
       bpr = null;
     }
   }
@@ -148,9 +162,11 @@ public class LineBreakpoint implements ClassLoadListener {
   protected void set() {
     dbg.addClassLoadListener(this); // class may not yet be loaded
     dbg.getEditor().addBreakpointedLine(line);
-    if (theClass != null && dbg.isPaused()) { // class is loaded
-      // immediately activate the breakpoint
-      attach();
+    if (className != null && dbg.isPaused()) { // debugging right now, try to attach
+      for (ReferenceType rt : dbg.getClasses()) {
+        // try to attach to all top level or nested classes
+        if (attach(rt)) break;
+      }
     }
     if (dbg.getEditor().isInCurrentTab(line)) {
       dbg.getEditor().getSketch().setModified(true);
@@ -191,12 +207,7 @@ public class LineBreakpoint implements ClassLoadListener {
   protected String className() {
     if (line.fileName().endsWith(".pde")) {
       // standard tab
-      ReferenceType mainClass = dbg.getMainClass();
-      //System.out.println(dbg.getMainClass().name());
-      if (mainClass == null) {
-        return null;
-      }
-      return dbg.getMainClass().name();
+      return dbg.getEditor().getSketch().getName();
     }
 
     if (line.fileName().endsWith(".java")) {
@@ -215,17 +226,18 @@ public class LineBreakpoint implements ClassLoadListener {
    */
   @Override
   public void classLoaded(ReferenceType theClass) {
-    // check if our class is being loaded
-    Messages.log("Class Loaded: " + theClass.name());
-    if (theClass.name().equals(className())) {
-      this.theClass = theClass;
-      attach();
-    }
-    for (ReferenceType ct : theClass.nestedTypes()) {
-      Messages.log("Nested " + ct.name());
+    if (!isAttached()) {
+      // try to attach
+      attach(theClass);
     }
   }
 
+  public String parseTopLevelClassName(String name) {
+    // Get rid of nested class name
+    int dollar = name.indexOf('$');
+    return (dollar == -1) ? name : name.substring(0, dollar);
+  }
+
 
   // . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .