diff --git a/archunit/src/main/java/com/tngtech/archunit/core/domain/Formatters.java b/archunit/src/main/java/com/tngtech/archunit/core/domain/Formatters.java
index a5a4628b3..4009de38b 100644
--- a/archunit/src/main/java/com/tngtech/archunit/core/domain/Formatters.java
+++ b/archunit/src/main/java/com/tngtech/archunit/core/domain/Formatters.java
@@ -118,7 +118,11 @@ public static String ensureSimpleName(String name) {
         int lastIndexOfDot = name.lastIndexOf('.');
         String partAfterDot = lastIndexOfDot >= 0 ? name.substring(lastIndexOfDot + 1) : name;
 
-        int lastIndexOf$ = partAfterDot.lastIndexOf('$');
+        int lastIndexOfNon$ = partAfterDot.length() - 1;
+        while(lastIndexOfNon$ > 0 && partAfterDot.charAt(lastIndexOfNon$) == '$') {
+            lastIndexOfNon$--;
+        }
+        int lastIndexOf$ = lastIndexOfNon$ > 0 ? partAfterDot.lastIndexOf('$', lastIndexOfNon$ - 1): -1;
         String simpleNameCandidate = lastIndexOf$ >= 0 ? partAfterDot.substring(lastIndexOf$ + 1) : partAfterDot;
 
         for (int i = 0; i < simpleNameCandidate.length(); i++) {
diff --git a/archunit/src/test/java/com/tngtech/archunit/core/domain/FormattersTest.java b/archunit/src/test/java/com/tngtech/archunit/core/domain/FormattersTest.java
index 4eef0db7a..cc61796b8 100644
--- a/archunit/src/test/java/com/tngtech/archunit/core/domain/FormattersTest.java
+++ b/archunit/src/test/java/com/tngtech/archunit/core/domain/FormattersTest.java
@@ -62,8 +62,13 @@ public static Object[][] simple_name_test_cases() {
                 $("", ""),
                 $("Dummy", "Dummy"),
                 $("org.example.Dummy", "Dummy"),
+                $("org.example.Dummy$", "Dummy$"),
+                $("org.example.Dummy$$", "Dummy$$"),
+                $("org.example.Dummy$$$", "Dummy$$$"),
+                $("org.example.$$$", "$$$"),
                 $("org.example.Dummy$123", ""),
                 $("org.example.Dummy$NestedClass", "NestedClass"),
+                $("org.example.Dummy$NestedClass$", "NestedClass$"),
                 $("org.example.Dummy$NestedClass123", "NestedClass123"),
                 $("org.example.Dummy$NestedClass$123", ""),
                 $("org.example.Dummy$NestedClass$MoreNestedClass", "MoreNestedClass"),