diff --git a/python/packages/core/agent_framework/observability.py b/python/packages/core/agent_framework/observability.py
index 391c77a3c5..9d36003bee 100644
--- a/python/packages/core/agent_framework/observability.py
+++ b/python/packages/core/agent_framework/observability.py
@@ -2159,8 +2159,10 @@ def _capture_messages(
     logging_messages = prepend_instructions_to_messages(normalized_messages, system_instructions)
     span_messages = [_to_otel_message(message) for message in normalized_messages]
     prepended_count = len(logging_messages) - len(normalized_messages)
-    for index, message in enumerate(logging_messages[:prepended_count]):
-        otel_message = _to_otel_message(message)
+    prepended_messages = [_to_otel_message(message) for message in logging_messages[:prepended_count]]
+    for index, (message, otel_message) in enumerate(
+        zip(logging_messages[:prepended_count], prepended_messages, strict=False)
+    ):
         # Reuse the otel message representation for logging instead of calling to_dict()
         # to avoid expensive Pydantic serialization overhead
         logger.info(
@@ -2171,8 +2173,9 @@ def _capture_messages(
                 MessageListTimestampFilter.INDEX_KEY: index,
             },
         )
-    for index, message in enumerate(normalized_messages, start=prepended_count):
-        otel_message = span_messages[index - prepended_count]
+    for index, (message, otel_message) in enumerate(
+        zip(normalized_messages, span_messages, strict=False), start=prepended_count
+    ):
         logger.info(
             otel_message,
             extra={