diff --git a/dd-java-agent/instrumentation/classloading/src/main/java/datadog/trace/instrumentation/classloading/ClassloadingInstrumentation.java b/dd-java-agent/instrumentation/classloading/src/main/java/datadog/trace/instrumentation/classloading/ClassloadingInstrumentation.java
index 0078c2bd2e..d2100abe8b 100644
--- a/dd-java-agent/instrumentation/classloading/src/main/java/datadog/trace/instrumentation/classloading/ClassloadingInstrumentation.java
+++ b/dd-java-agent/instrumentation/classloading/src/main/java/datadog/trace/instrumentation/classloading/ClassloadingInstrumentation.java
@@ -71,32 +71,39 @@ public final class ClassloadingInstrumentation extends Instrumenter.Default {
 
   public static class LoadClassAdvice {
     @Advice.OnMethodEnter(skipOn = Advice.OnNonDefaultValue.class)
-    public static Class<?> onEnter(
-        @Advice.Argument(0) final String name, @Advice.Local("_callDepth") int callDepth) {
-      callDepth = CallDepthThreadLocalMap.incrementCallDepth(ClassLoader.class);
+    public static Class<?> onEnter(@Advice.Argument(0) final String name) {
+      // need to use call depth here to prevent re-entry from call to Class.forName() below
+      // because on some JVMs (e.g. IBM's, though IBM bootstrap loader is explicitly excluded above)
+      // Class.forName() ends up calling loadClass() on the bootstrap loader which would then come
+      // back to this instrumentation over and over, causing a StackOverflowError
+      final int callDepth = CallDepthThreadLocalMap.incrementCallDepth(ClassLoader.class);
       if (callDepth > 0) {
         return null;
       }
-      for (final String prefix : Constants.BOOTSTRAP_PACKAGE_PREFIXES) {
-        if (name.startsWith(prefix)) {
-          try {
-            return Class.forName(name, false, null);
-          } catch (final ClassNotFoundException e) {
+      try {
+        for (final String prefix : Constants.BOOTSTRAP_PACKAGE_PREFIXES) {
+          if (name.startsWith(prefix)) {
+            try {
+              return Class.forName(name, false, null);
+            } catch (final ClassNotFoundException e) {
+            }
           }
         }
+      } finally {
+        // need to reset it right away, not waiting until onExit()
+        // otherwise it will prevent this instrumentation from being applied when loadClass()
+        // ends up calling a ClassFileTransformer which ends up calling loadClass() further down the
+        // stack on one of our bootstrap packages (since the call depth check would then suppress
+        // the nested loadClass instrumentation)
+        CallDepthThreadLocalMap.reset(ClassLoader.class);
       }
       return null;
     }
 
     @Advice.OnMethodExit(onThrowable = Throwable.class)
     public static void onExit(
-        @Advice.Local("_callDepth") final int callDepth,
         @Advice.Return(readOnly = false) Class<?> result,
         @Advice.Enter final Class<?> resultFromBootstrapLoader) {
-      if (callDepth > 0) {
-        return;
-      }
-      CallDepthThreadLocalMap.reset(ClassLoader.class);
       if (resultFromBootstrapLoader != null) {
         result = resultFromBootstrapLoader;
       }