diff --git a/src/main/java/com/squareup/javapoet/ClassName.java b/src/main/java/com/squareup/javapoet/ClassName.java
index 6d1abd8c7..3617c51a4 100644
--- a/src/main/java/com/squareup/javapoet/ClassName.java
+++ b/src/main/java/com/squareup/javapoet/ClassName.java
@@ -51,7 +51,7 @@ private ClassName(List<String> names, List<AnnotationSpec> annotations) {
     this.names = Util.immutableList(names);
     this.canonicalName = (names.get(0).isEmpty()
         ? Util.join(".", names.subList(1, names.size()))
-        : Util.join(".", names)).replace(".$", "$");
+        : Util.join(".", names));
   }
 
   @Override public ClassName annotated(List<AnnotationSpec> annotations) {
@@ -141,16 +141,13 @@ public static ClassName get(Class<?> clazz) {
     checkArgument(!clazz.isArray(), "array types cannot be represented as a ClassName");
     List<String> names = new ArrayList<>();
     while (true) {
-      if (clazz.isAnonymousClass()) {
-        int lastDot = clazz.getName().lastIndexOf('.');
-        if (lastDot != -1) {
-          String anonClassName = clazz.getName().substring(lastDot + 1);
-          int lastDollar = anonClassName.lastIndexOf('$');
-          names.add(anonClassName.substring(lastDollar));
-        }
-      } else {
-        names.add(clazz.getSimpleName());
+      String anonymousSuffix = "";
+      while (clazz.isAnonymousClass()) {
+        int lastDollar = clazz.getName().lastIndexOf('$');
+        anonymousSuffix = clazz.getName().substring(lastDollar) + anonymousSuffix;
+        clazz = clazz.getEnclosingClass();
       }
+      names.add(clazz.getSimpleName() + anonymousSuffix);
       Class<?> enclosing = clazz.getEnclosingClass();
       if (enclosing == null) break;
       clazz = enclosing;
diff --git a/src/test/java/com/squareup/javapoet/ClassNameTest.java b/src/test/java/com/squareup/javapoet/ClassNameTest.java
index 1544814f8..0488213d8 100644
--- a/src/test/java/com/squareup/javapoet/ClassNameTest.java
+++ b/src/test/java/com/squareup/javapoet/ClassNameTest.java
@@ -96,10 +96,18 @@ private void assertBestGuessThrows(String s) {
     assertThat(baz).isEqualTo(ClassName.get("com.example", "Foo", "Bar", "Baz"));
   }
 
+  static class $Outer {
+    static class $Inner {}
+  }
+
   @Test public void classNameFromTypeElement() {
     Elements elements = compilationRule.getElements();
-    TypeElement element = elements.getTypeElement(Object.class.getCanonicalName());
-    assertThat(ClassName.get(element).toString()).isEqualTo("java.lang.Object");
+    TypeElement object = elements.getTypeElement(Object.class.getCanonicalName());
+    assertThat(ClassName.get(object).toString()).isEqualTo("java.lang.Object");
+    TypeElement outer = elements.getTypeElement($Outer.class.getCanonicalName());
+    assertThat(ClassName.get(outer).toString()).isEqualTo("com.squareup.javapoet.ClassNameTest.$Outer");
+    TypeElement inner = elements.getTypeElement($Outer.$Inner.class.getCanonicalName());
+    assertThat(ClassName.get(inner).toString()).isEqualTo("com.squareup.javapoet.ClassNameTest.$Outer.$Inner");
   }
 
   @Test public void classNameFromClass() {
@@ -109,6 +117,12 @@ private void assertBestGuessThrows(String s) {
         .isEqualTo("com.squareup.javapoet.ClassNameTest.OuterClass.InnerClass");
     assertThat((ClassName.get(new Object() {}.getClass())).toString())
         .isEqualTo("com.squareup.javapoet.ClassNameTest$1");
+    assertThat((ClassName.get(new Object() { Object inner = new Object() {}; }.inner.getClass())).toString())
+        .isEqualTo("com.squareup.javapoet.ClassNameTest$2$1");
+    assertThat((ClassName.get($Outer.class)).toString())
+        .isEqualTo("com.squareup.javapoet.ClassNameTest.$Outer");
+    assertThat((ClassName.get($Outer.$Inner.class)).toString())
+        .isEqualTo("com.squareup.javapoet.ClassNameTest.$Outer.$Inner");
   }
 
   @Test public void peerClass() {