diff --git a/src/main/java/com/android/tools/r8/retrace/internal/RetraceUtils.java b/src/main/java/com/android/tools/r8/retrace/internal/RetraceUtils.java
index 076f68a..46e8ddc 100644
--- a/src/main/java/com/android/tools/r8/retrace/internal/RetraceUtils.java
+++ b/src/main/java/com/android/tools/r8/retrace/internal/RetraceUtils.java
@@ -57,14 +57,14 @@
   }
 
   public static boolean hasPredictableSourceFileName(String originalClassName, String sourceFile) {
-    String synthesizedSourceFileName = getClassSimpleName(originalClassName) + ".java";
+    String synthesizedSourceFileName = getOuterClassSimpleName(originalClassName) + ".java";
     return synthesizedSourceFileName.equals(sourceFile);
   }
 
-  private static String getClassSimpleName(String clazz) {
-    int lastIndexOfPeriod = clazz.lastIndexOf('.');
+  private static String getOuterClassSimpleName(String clazz) {
+    int lastIndexOfPeriod = clazz.lastIndexOf(DescriptorUtils.JAVA_PACKAGE_SEPARATOR);
     // Check if we can find a subclass separator.
-    int endIndex = clazz.lastIndexOf('$');
+    int endIndex = clazz.indexOf(DescriptorUtils.INNER_CLASS_SEPARATOR, lastIndexOfPeriod);
     if (lastIndexOfPeriod > endIndex || endIndex < 0) {
       endIndex = clazz.length();
     }
@@ -120,9 +120,9 @@
       // We have no mapping but but file name is unknown, so the best we can do is take the
       // name of the obfuscated clazz.
       assert minifiedClassName.equals(retracedClassName);
-      return getClassSimpleName(minifiedClassName) + "." + extension;
+      return getOuterClassSimpleName(minifiedClassName) + "." + extension;
     }
-    String newFileName = getClassSimpleName(retracedClassName);
+    String newFileName = getOuterClassSimpleName(retracedClassName);
     return newFileName + "." + extension;
   }
 
diff --git a/src/test/java/com/android/tools/r8/retrace/RetraceTests.java b/src/test/java/com/android/tools/r8/retrace/RetraceTests.java
index 6949ad4..edcb118 100644
--- a/src/test/java/com/android/tools/r8/retrace/RetraceTests.java
+++ b/src/test/java/com/android/tools/r8/retrace/RetraceTests.java
@@ -27,6 +27,7 @@
 import com.android.tools.r8.retrace.stacktraces.CircularReferenceStackTrace;
 import com.android.tools.r8.retrace.stacktraces.FileNameExtensionStackTrace;
 import com.android.tools.r8.retrace.stacktraces.InlineFileNameStackTrace;
+import com.android.tools.r8.retrace.stacktraces.InlineFileNameWithInnerClassesStackTrace;
 import com.android.tools.r8.retrace.stacktraces.InlineNoLineNumberStackTrace;
 import com.android.tools.r8.retrace.stacktraces.InlineSourceFileContextStackTrace;
 import com.android.tools.r8.retrace.stacktraces.InlineWithLineNumbersStackTrace;
@@ -86,6 +87,11 @@
   }
 
   @Test
+  public void testInlineFileNameWithInnerClassesStackTrace() {
+    runRetraceTest(new InlineFileNameWithInnerClassesStackTrace());
+  }
+
+  @Test
   public void testNullLineTrace() {
     TestDiagnosticMessagesImpl diagnosticsHandler = new TestDiagnosticMessagesImpl();
     NullStackTrace nullStackTrace = new NullStackTrace();
diff --git a/src/test/java/com/android/tools/r8/retrace/stacktraces/InlineFileNameWithInnerClassesStackTrace.java b/src/test/java/com/android/tools/r8/retrace/stacktraces/InlineFileNameWithInnerClassesStackTrace.java
new file mode 100644
index 0000000..20ed6ec
--- /dev/null
+++ b/src/test/java/com/android/tools/r8/retrace/stacktraces/InlineFileNameWithInnerClassesStackTrace.java
@@ -0,0 +1,40 @@
+// Copyright (c) 2020, the R8 project authors. Please see the AUTHORS file
+// for details. All rights reserved. Use of this source code is governed by a
+// BSD-style license that can be found in the LICENSE file.
+
+package com.android.tools.r8.retrace.stacktraces;
+
+import com.android.tools.r8.utils.StringUtils;
+import java.util.Arrays;
+import java.util.List;
+
+public class InlineFileNameWithInnerClassesStackTrace implements StackTraceForTest {
+
+  @Override
+  public List<String> obfuscatedStackTrace() {
+    return Arrays.asList(
+        "Exception in thread \"main\" java.lang.NullPointerException",
+        "\tat com.android.tools.r8.naming.retrace.Main.main(Main.dummy:3)");
+  }
+
+  @Override
+  public List<String> retracedStackTrace() {
+    return Arrays.asList(
+        "Exception in thread \"main\" java.lang.NullPointerException",
+        "\tat foo.Bar$Baz$Qux.baz(Bar.dummy:0)",
+        "\tat com.android.tools.r8.naming.retrace.Main.main(Main.dummy:7)");
+  }
+
+  @Override
+  public String mapping() {
+    return StringUtils.lines(
+        "com.android.tools.r8.naming.retrace.Main -> com.android.tools.r8.naming.retrace.Main:",
+        "    3:3:void foo.Bar$Baz$Qux.baz(long):0:0 -> main",
+        "    3:3:void main(java.lang.String[]):7 -> main");
+  }
+
+  @Override
+  public int expectedWarnings() {
+    return 0;
+  }
+}