diff --git a/javaagent-tooling/src/main/java/io/opentelemetry/javaagent/tooling/instrumentation/TypeTransformerImpl.java b/javaagent-tooling/src/main/java/io/opentelemetry/javaagent/tooling/instrumentation/TypeTransformerImpl.java
index 1382acc66e2d..e3b6285d334b 100644
--- a/javaagent-tooling/src/main/java/io/opentelemetry/javaagent/tooling/instrumentation/TypeTransformerImpl.java
+++ b/javaagent-tooling/src/main/java/io/opentelemetry/javaagent/tooling/instrumentation/TypeTransformerImpl.java
@@ -8,6 +8,7 @@
 import io.opentelemetry.javaagent.extension.instrumentation.TypeTransformer;
 import io.opentelemetry.javaagent.tooling.Utils;
 import io.opentelemetry.javaagent.tooling.bytebuddy.ExceptionHandlers;
+import io.opentelemetry.javaagent.tooling.instrumentation.indy.ForceDynamicallyTypedAssignReturnedFactory;
 import net.bytebuddy.agent.builder.AgentBuilder;
 import net.bytebuddy.asm.Advice;
 import net.bytebuddy.description.method.MethodDescription;
@@ -21,7 +22,9 @@ final class TypeTransformerImpl implements TypeTransformer {
     this.agentBuilder = agentBuilder;
     adviceMapping =
         Advice.withCustomMapping()
-            .with(new Advice.AssignReturned.Factory().withSuppressed(Throwable.class));
+            .with(
+                new ForceDynamicallyTypedAssignReturnedFactory(
+                    new Advice.AssignReturned.Factory().withSuppressed(Throwable.class)));
   }
 
   @Override
diff --git a/javaagent-tooling/src/main/java/io/opentelemetry/javaagent/tooling/instrumentation/indy/ForceDynamicallyTypedAssignReturnedFactory.java b/javaagent-tooling/src/main/java/io/opentelemetry/javaagent/tooling/instrumentation/indy/ForceDynamicallyTypedAssignReturnedFactory.java
index d107f08209e0..dd0c88bb4752 100644
--- a/javaagent-tooling/src/main/java/io/opentelemetry/javaagent/tooling/instrumentation/indy/ForceDynamicallyTypedAssignReturnedFactory.java
+++ b/javaagent-tooling/src/main/java/io/opentelemetry/javaagent/tooling/instrumentation/indy/ForceDynamicallyTypedAssignReturnedFactory.java
@@ -20,6 +20,14 @@
 import net.bytebuddy.implementation.bytecode.assign.Assigner;
 import net.bytebuddy.matcher.ElementMatchers;
 
+/**
+ * This factory is designed to wrap around {@link Advice.PostProcessor.Factory} and ensures that
+ * {@link net.bytebuddy.implementation.bytecode.assign.Assigner.Typing#DYNAMIC} is used everywhere.
+ *
+ * <p>This helps by avoiding errors where the instrumented bytecode is suddenly unloadable due to
+ * incompatible assignments and preventing cluttering advice code annotations with the explicit
+ * typing.
+ */
 public class ForceDynamicallyTypedAssignReturnedFactory implements Advice.PostProcessor.Factory {
 
   private static final String TO_ARGUMENTS_TYPENAME =