diff --git a/dd-java-agent/agent-tooling/src/main/java/datadog/trace/agent/tooling/muzzle/Reference.java b/dd-java-agent/agent-tooling/src/main/java/datadog/trace/agent/tooling/muzzle/Reference.java
index dd18d88d9e..e288d87fa3 100644
--- a/dd-java-agent/agent-tooling/src/main/java/datadog/trace/agent/tooling/muzzle/Reference.java
+++ b/dd-java-agent/agent-tooling/src/main/java/datadog/trace/agent/tooling/muzzle/Reference.java
@@ -102,6 +102,11 @@ public class Reference {
     return merged;
   }
 
+  @Override
+  public String toString() {
+    return "Reference<" + className + ">";
+  }
+
   public static class Source {
     private final String name;
     private final int line;
@@ -193,16 +198,25 @@ public class Reference {
     /** Fallback mismatch in case an unexpected exception occurs during reference checking. */
     public static class ReferenceCheckError extends Mismatch {
       private final Exception referenceCheckExcetpion;
+      private final Reference referenceBeingChecked;
+      private final ClassLoader classLoaderBeingChecked;
 
-      public ReferenceCheckError(Exception e) {
+      public ReferenceCheckError(
+          Exception e, Reference referenceBeingChecked, ClassLoader classLoaderBeingChecked) {
         super(new Source[0]);
         this.referenceCheckExcetpion = e;
+        this.referenceBeingChecked = referenceBeingChecked;
+        this.classLoaderBeingChecked = classLoaderBeingChecked;
       }
 
       @Override
       String getMismatchDetails() {
         final StringWriter sw = new StringWriter();
-        sw.write("Failed to generate reference check: ");
+        sw.write("Failed to generate reference check for: ");
+        sw.write(referenceBeingChecked.toString());
+        sw.write(" on classloader ");
+        sw.write(classLoaderBeingChecked.toString());
+        sw.write("\n");
         // add exception message and stack trace
         final PrintWriter pw = new PrintWriter(sw);
         referenceCheckExcetpion.printStackTrace(pw);
diff --git a/dd-java-agent/agent-tooling/src/main/java/datadog/trace/agent/tooling/muzzle/ReferenceMatcher.java b/dd-java-agent/agent-tooling/src/main/java/datadog/trace/agent/tooling/muzzle/ReferenceMatcher.java
index dcccbecd17..13b093fd33 100644
--- a/dd-java-agent/agent-tooling/src/main/java/datadog/trace/agent/tooling/muzzle/ReferenceMatcher.java
+++ b/dd-java-agent/agent-tooling/src/main/java/datadog/trace/agent/tooling/muzzle/ReferenceMatcher.java
@@ -101,7 +101,7 @@ public class ReferenceMatcher {
       }
     } catch (Exception e) {
       // Shouldn't happen. Fail the reference check and add a mismatch for debug logging.
-      mismatches.add(new Mismatch.ReferenceCheckError(e));
+      mismatches.add(new Mismatch.ReferenceCheckError(e, reference, loader));
     }
     return mismatches;
   }
@@ -134,6 +134,12 @@ public class ReferenceMatcher {
     private final List<Field> fields = new ArrayList<>();
 
     public static UnloadedType of(String className, ClassLoader classLoader) throws Exception {
+      if (classLoader != Utils.getBootstrapProxy()) {
+        // getResource delegation won't see our bootstrap classes so do the delegation here.
+        if (Utils.getBootstrapProxy().getResource(Utils.getResourceName(className)) != null) {
+          return of(className, Utils.getBootstrapProxy());
+        }
+      }
       className = Utils.getInternalName(className);
       Map<String, UnloadedType> classLoaderCache = typeCache.get(classLoader);
       if (classLoaderCache == null) {