diff --git a/classpath/avian/SystemClassLoader.java b/classpath/avian/SystemClassLoader.java
index 71759c7a54..ce9cdcd7a3 100644
--- a/classpath/avian/SystemClassLoader.java
+++ b/classpath/avian/SystemClassLoader.java
@@ -17,6 +17,7 @@ import java.util.Collection;
 import java.util.Collections;
 import java.util.ArrayList;
 import java.util.Enumeration;
+import java.util.NoSuchElementException;
 
 public class SystemClassLoader extends ClassLoader {
   private native VMClass findVMClass(String name)
@@ -106,20 +107,51 @@ public class SystemClassLoader extends ClassLoader {
       }
     }
 
-    URL url = findResource(name);
-    if (url != null) {
-      urls.add(url);
+    Enumeration<URL> urls2 = findResources(name);
+    while (urls2.hasMoreElements()) {
+      urls.add(urls2.nextElement());
     }
 
     return Collections.enumeration(urls);
   }
 
+  private class ResourceEnumeration implements Enumeration<URL> {
+    private long[] finderElementPtrPtr;
+    private String name, urlPrefix;
+
+    public ResourceEnumeration(String name) {
+      this.name = name;
+      finderElementPtrPtr = new long[1];
+      urlPrefix = nextResourceURLPrefix();
+    }
+
+    private native String nextResourceURLPrefix(SystemClassLoader loader,
+      String name, long[] finderElementPtrPtr);
+
+    private String nextResourceURLPrefix() {
+      return nextResourceURLPrefix(SystemClassLoader.this, name,
+        finderElementPtrPtr);
+    }
+
+    public boolean hasMoreElements() {
+      return urlPrefix != null;
+    }
+
+    public URL nextElement() {
+      if (urlPrefix == null) throw new NoSuchElementException();
+      URL result;
+      try {
+        result = new URL(urlPrefix + name);
+      } catch (MalformedURLException ignored) {
+        result = null;
+      }
+      if (finderElementPtrPtr[0] == 0l) urlPrefix = null;
+      else urlPrefix = nextResourceURLPrefix();
+      return result;
+    }
+  }
+
   protected Enumeration<URL> findResources(String name) {
-    Collection<URL> urls = new ArrayList(1);
-    URL url = findResource(name);
-    if (url != null) {
-      urls.add(url);
-    }
-    return Collections.enumeration(urls);
+    return new ResourceEnumeration(name);
   }
 }
diff --git a/classpath/avian/jar/Handler.java b/classpath/avian/jar/Handler.java
index 3b5f64fd5f..726f12e413 100644
--- a/classpath/avian/jar/Handler.java
+++ b/classpath/avian/jar/Handler.java
@@ -42,7 +42,7 @@ public class Handler extends URLStreamHandler {
         ("protocol " + file.getProtocol() + " not yet supported");
     }
 
-    url.set("jar", "", -1, s, null);
+    url.set("jar", null, -1, s, null);
   }
 
   private static class MyJarURLConnection extends JarURLConnection {
diff --git a/makefile b/makefile
index c55ce91aed..113593478b 100755
--- a/makefile
+++ b/makefile
@@ -1487,13 +1487,20 @@ ifeq ($(continuations),true)
 $(build)/compile-x86-asm.o: $(src)/continuations-x86.$(asm-format)
 endif
 
-$(build)/run-tests.sh: $(test-classes) makefile
+$(build)/run-tests.sh: $(test-classes) makefile $(build)/extra-dir/multi-classpath-test.txt $(build)/test/multi-classpath-test.txt
 	echo 'cd $$(dirname $$0)' > $(@)
 	echo "sh ./test.sh 2>/dev/null \\" >> $(@)
-	echo "$(shell echo $(library-path) | sed 's|$(build)|\.|g') ./$(name)-unittest${exe-suffix} ./$(notdir $(test-executable)) $(mode) \"-Djava.library.path=. -cp test\" \\" >> $(@)
+	echo "$(shell echo $(library-path) | sed 's|$(build)|\.|g') ./$(name)-unittest${exe-suffix} ./$(notdir $(test-executable)) $(mode) \"-Djava.library.path=. -cp test:extra-dir\" \\" >> $(@)
 	echo "$(call class-names,$(test-build),$(filter-out $(test-support-classes), $(test-classes))) \\" >> $(@)
 	echo "$(continuation-tests) $(tail-tests)" >> $(@)
 
+$(build)/extra-dir/multi-classpath-test.txt:
+	mkdir -p $(build)/extra-dir
+	echo "$@" > $@
+
+$(build)/test/multi-classpath-test.txt:
+	echo "$@" > $@
+
 $(build)/test.sh: $(test)/test.sh
 	cp $(<) $(@)
 
diff --git a/src/avian/finder.h b/src/avian/finder.h
index cf92044b72..c7fdbd547b 100644
--- a/src/avian/finder.h
+++ b/src/avian/finder.h
@@ -168,6 +168,7 @@ class Finder {
                                 unsigned* length,
                                 bool tryDirectory = false) = 0;
   virtual const char* urlPrefix(const char* name) = 0;
+  virtual const char* nextUrlPrefix(const char* name, void *&finderElementPtr) = 0;
   virtual const char* sourceUrl(const char* name) = 0;
   virtual const char* path() = 0;
   virtual void dispose() = 0;
diff --git a/src/builtin.cpp b/src/builtin.cpp
index f7f9a28d53..7fda369dbf 100644
--- a/src/builtin.cpp
+++ b/src/builtin.cpp
@@ -152,6 +152,30 @@ Avian_avian_SystemClassLoader_resourceURLPrefix
   }
 }
 
+extern "C" JNIEXPORT int64_t JNICALL
+Avian_avian_SystemClassLoader_00024ResourceEnumeration_nextResourceURLPrefix
+(Thread* t, object, uintptr_t* arguments)
+{
+  object loader = reinterpret_cast<object>(arguments[1]);
+  object name = reinterpret_cast<object>(arguments[2]);
+  object finderElementPtrPtr = reinterpret_cast<object>(arguments[3]);
+
+  if (LIKELY(name) && LIKELY(finderElementPtrPtr)) {
+    THREAD_RUNTIME_ARRAY(t, char, n, stringLength(t, name) + 1);
+    stringChars(t, name, RUNTIME_ARRAY_BODY(n));
+
+    void *&finderElementPtr = reinterpret_cast<void *&>(longArrayBody(t,
+      finderElementPtrPtr, 0));
+    const char* name = static_cast<Finder*>
+      (systemClassLoaderFinder(t, loader))->nextUrlPrefix(RUNTIME_ARRAY_BODY(n),
+        finderElementPtr);
+
+    return name ? reinterpret_cast<uintptr_t>(makeString(t, "%s", name)) : 0;
+  } else {
+    throwNew(t, Machine::NullPointerExceptionType);
+  }
+}
+
 extern "C" JNIEXPORT int64_t JNICALL
 Avian_avian_SystemClassLoader_getClass
 (Thread* t, object, uintptr_t* arguments)
diff --git a/src/finder.cpp b/src/finder.cpp
index b170abc6e7..27969321ba 100644
--- a/src/finder.cpp
+++ b/src/finder.cpp
@@ -908,7 +908,16 @@ class MyFinder: public Finder {
   }
 
   virtual const char* urlPrefix(const char* name) {
-    for (Element* e = path_; e; e = e->next) {
+    void *finderElementPtr = NULL;
+    return nextUrlPrefix(name, finderElementPtr);
+  }
+
+  virtual const char* nextUrlPrefix(const char* name,
+      void *&finderElementPtr)
+  {
+    Element *&e = reinterpret_cast<Element*&>(finderElementPtr);
+    e = e ? e->next : path_;
+    for (; e; e = e->next) {
       unsigned length;
       System::FileType type = e->stat(name, &length, true);
       if (type != System::TypeDoesNotExist) {
diff --git a/test/Misc.java b/test/Misc.java
index 91195d5f13..b0fde2d44b 100644
--- a/test/Misc.java
+++ b/test/Misc.java
@@ -1,3 +1,7 @@
+import java.io.IOException;
+import java.net.URL;
+import java.util.Enumeration;
+
 public class Misc {
   private static class μClass {
     public int μField;
@@ -262,6 +266,27 @@ public class Misc {
 
     expect((Protected.class.getModifiers() & java.lang.reflect.Modifier.PUBLIC)
            == 0);
+
+    try {
+      int count = 0;
+      boolean test = false, extraDir = false;
+      ClassLoader loader = Misc.class.getClassLoader();
+      Enumeration<URL> resources = loader.getResources("multi-classpath-test.txt");
+      while (resources.hasMoreElements()) {
+        ++count;
+        String url = resources.nextElement().toString();
+        if (url.contains("extra-dir")) {
+          extraDir = true;
+        } else if (url.contains("test")) {
+          test = true;
+        }
+      }
+      expect(count == 2);
+      expect(test);
+      expect(extraDir);
+    } catch (IOException e) {
+      throw new RuntimeException(e);
+    }
   }
 
   protected class Protected { }