From 877a684f4b55ac2fd4ddca9aea49cc50a6ce55e9 Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Mon, 16 Mar 2026 15:01:08 +0000
Subject: [PATCH 01/10] Initial plan


From 113e17c097b53126963b16166fb6336b7d1094d2 Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Mon, 16 Mar 2026 15:20:34 +0000
Subject: [PATCH 02/10] Replace assert statements with explicit TypeError
 raises in langchain utils

Replace all 30 assert statements in utils.py with equivalent
if-not-raise TypeError checks. This ensures type validation is not
silently stripped when Python runs with -O (optimized mode).

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>
---
 .../core/exporters/agent365_exporter.py       |  68 ++++++++----
 .../observability/core/opentelemetry_scope.py |  16 ++-
 .../extensions/langchain/utils.py             | 104 ++++++++++--------
 .../extensions/openai/trace_processor.py      |  31 ++++--
 .../observability/extensions/openai/utils.py  |   4 +-
 5 files changed, 145 insertions(+), 78 deletions(-)

diff --git a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
index 27b54e23..5cce2dd7 100644
--- a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
+++ b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
@@ -86,9 +86,9 @@ def export(self, spans: Sequence[ReadableSpan]) -> SpanExportResult:
                 logger.info("No spans with tenant/agent identity found; nothing exported.")
                 return SpanExportResult.SUCCESS
 
-            # Debug: Log number of groups and total span count
+            # Log number of groups and total span count
             total_spans = sum(len(activities) for activities in groups.values())
-            logger.info(
+            logger.debug(
                 f"Found {len(groups)} identity groups with {total_spans} total spans to export"
             )
 
@@ -105,8 +105,8 @@ def export(self, spans: Sequence[ReadableSpan]) -> SpanExportResult:
 
                 url = build_export_url(endpoint, agent_id, tenant_id, self._use_s2s_endpoint)
 
-                # Debug: Log endpoint being used
-                logger.info(
+                # Log endpoint details at DEBUG to avoid leaking IDs in production logs
+                logger.debug(
                     f"Exporting {len(activities)} spans to endpoint: {url} "
                     f"(tenant: {tenant_id}, agent: {agent_id})"
                 )
@@ -115,15 +115,19 @@ def export(self, spans: Sequence[ReadableSpan]) -> SpanExportResult:
                 try:
                     token = self._token_resolver(agent_id, tenant_id)
                     if token:
+                        # Warn if sending bearer token over non-HTTPS connection
+                        if not url.lower().startswith("https://"):
+                            logger.warning(
+                                "Bearer token is being sent over a non-HTTPS connection. "
+                                "This may expose credentials in transit."
+                            )
                         headers["authorization"] = f"Bearer {token}"
-                        logger.info(f"Token resolved successfully for agent {agent_id}")
+                        logger.debug("Token resolved successfully.")
                     else:
-                        logger.info(f"No token returned for agent {agent_id}")
+                        logger.debug("No token returned by resolver.")
                 except Exception as e:
                     # If token resolution fails, treat as failure for this group
-                    logger.error(
-                        f"Token resolution failed for agent {agent_id}, tenant {tenant_id}: {e}"
-                    )
+                    logger.error(f"Token resolution failed: {type(e).__name__}")
                     any_failure = True
                     continue
 
@@ -162,6 +166,21 @@ def _truncate_text(text: str, max_length: int) -> str:
             return text[:max_length] + "..."
         return text
 
+    @staticmethod
+    def _parse_retry_after(resp: requests.Response) -> float | None:
+        """Parse the Retry-After header from a response.
+
+        Returns:
+            The number of seconds to wait, or None if the header is absent or invalid.
+        """
+        retry_after = resp.headers.get("Retry-After")
+        if retry_after is None:
+            return None
+        try:
+            return float(retry_after)
+        except (ValueError, TypeError):
+            return None
+
     def _post_with_retries(self, url: str, body: str, headers: dict[str, str]) -> bool:
         for attempt in range(DEFAULT_MAX_RETRIES + 1):
             try:
@@ -181,43 +200,46 @@ def _post_with_retries(self, url: str, body: str, headers: dict[str, str]) -> bo
 
                 # 2xx => success
                 if 200 <= resp.status_code < 300:
-                    logger.info(
+                    logger.debug(
                         f"HTTP {resp.status_code} success on attempt {attempt + 1}. "
-                        f"Correlation ID: {correlation_id}. "
-                        f"Response: {self._truncate_text(resp.text, 200)}"
+                        f"Correlation ID: {correlation_id}."
                     )
                     return True
 
-                # Log non-success responses
-                response_text = self._truncate_text(resp.text, 500)
-
                 # Retry transient
                 if resp.status_code in (408, 429) or 500 <= resp.status_code < 600:
+                    # Respect Retry-After header for 429 responses
+                    retry_after = self._parse_retry_after(resp)
                     if attempt < DEFAULT_MAX_RETRIES:
-                        time.sleep(0.2 * (attempt + 1))
+                        if retry_after is not None:
+                            time.sleep(min(retry_after, 60.0))
+                        else:
+                            # Exponential backoff with base 0.5s
+                            time.sleep(0.5 * (2**attempt))
                         continue
                     # Final attempt failed
                     logger.error(
-                        f"HTTP {resp.status_code} final failure after {DEFAULT_MAX_RETRIES + 1} attempts. "
-                        f"Correlation ID: {correlation_id}. "
-                        f"Response: {response_text}"
+                        f"HTTP {resp.status_code} final failure after "
+                        f"{DEFAULT_MAX_RETRIES + 1} attempts. "
+                        f"Correlation ID: {correlation_id}."
                     )
                 else:
                     # Non-retryable error
                     logger.error(
                         f"HTTP {resp.status_code} non-retryable error. "
-                        f"Correlation ID: {correlation_id}. "
-                        f"Response: {response_text}"
+                        f"Correlation ID: {correlation_id}."
                     )
                 return False
 
             except requests.RequestException as e:
                 if attempt < DEFAULT_MAX_RETRIES:
-                    time.sleep(0.2 * (attempt + 1))
+                    # Exponential backoff with base 0.5s
+                    time.sleep(0.5 * (2**attempt))
                     continue
                 # Final attempt failed
                 logger.error(
-                    f"Request failed after {DEFAULT_MAX_RETRIES + 1} attempts with exception: {e}"
+                    f"Request failed after {DEFAULT_MAX_RETRIES + 1} attempts: "
+                    f"{type(e).__name__}"
                 )
                 return False
         return False
diff --git a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/opentelemetry_scope.py b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/opentelemetry_scope.py
index 93255439..cf4e2814 100644
--- a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/opentelemetry_scope.py
+++ b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/opentelemetry_scope.py
@@ -126,6 +126,7 @@ def __init__(
         self._error_type: str | None = None
         self._exception: Exception | None = None
         self._context_token = None
+        self._baggage_tokens: list[object] = []
 
         if self._is_telemetry_enabled():
             tracer = self._get_tracer()
@@ -244,6 +245,12 @@ def set_tag_maybe(self, name: str, value: Any) -> None:
     def add_baggage(self, key: str, value: str) -> None:
         """Add baggage to the current context.
 
+        .. warning::
+            This method attaches a new context that cannot be detached. Prefer using
+            :class:`~microsoft_agents_a365.observability.core.middleware.baggage_builder.BaggageBuilder`
+            with its context-manager API (``with builder.build(): ...``) which properly
+            restores the previous context on exit.
+
         Args:
             key: The baggage key
             value: The baggage value
@@ -254,7 +261,9 @@ def add_baggage(self, key: str, value: str) -> None:
             # This will be inherited by child spans created within this context
             baggage_context = baggage.set_baggage(key, value)
             # The context needs to be made current for child spans to inherit the baggage
-            context.attach(baggage_context)
+            token = context.attach(baggage_context)
+            # Store the token so it can be detached when the scope ends
+            self._baggage_tokens.append(token)
 
     def record_attributes(self, attributes: dict[str, Any] | list[tuple[str, Any]]) -> None:
         """Record multiple attribute key/value pairs for telemetry tracking.
@@ -294,6 +303,11 @@ def _end(self) -> None:
             span_id = f"{self._span.context.span_id:016x}" if self._span.context else "unknown"
             logger.info(f"Span ended: '{self._span.name}' ({span_id})")
 
+            # Detach any baggage tokens in reverse order
+            for token in reversed(self._baggage_tokens):
+                context.detach(token)
+            self._baggage_tokens.clear()
+
             # Convert custom end time to OTel-compatible format (nanoseconds since epoch)
             otel_end_time = self._datetime_to_ns(self._custom_end_time)
             if otel_end_time is not None:
diff --git a/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/utils.py b/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/utils.py
index b081e44e..871b1fb1 100644
--- a/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/utils.py
+++ b/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/utils.py
@@ -53,7 +53,8 @@ def prompts(inputs: Mapping[str, Any] | None) -> Iterator[tuple[str, list[str]]]
     """Yields prompts if present."""
     if not inputs:
         return
-    assert hasattr(inputs, "get"), f"expected Mapping, found {type(inputs)}"
+    if not hasattr(inputs, "get"):
+        raise TypeError(f"expected Mapping, found {type(inputs)}")
     if prompts := inputs.get("prompts"):
         yield GEN_AI_SYSTEM_INSTRUCTIONS_KEY, prompts
 
@@ -62,17 +63,21 @@ def prompts(inputs: Mapping[str, Any] | None) -> Iterator[tuple[str, list[str]]]
 def _extract_message_kwargs(message_data: Mapping[str, Any] | None) -> Iterator[[str, Any]]:
     if not message_data:
         return
-    assert hasattr(message_data, "get"), f"expected Mapping, found {type(message_data)}"
+    if not hasattr(message_data, "get"):
+        raise TypeError(f"expected Mapping, found {type(message_data)}")
     if kwargs := message_data.get("kwargs"):
-        assert hasattr(kwargs, "get"), f"expected Mapping, found {type(kwargs)}"
+        if not hasattr(kwargs, "get"):
+            raise TypeError(f"expected Mapping, found {type(kwargs)}")
         if content := kwargs.get("content"):
             # Just yield as-is (string or list)
             yield "message.content", content
         if tool_call_id := kwargs.get("tool_call_id"):
-            assert isinstance(tool_call_id, str), f"expected str, found {type(tool_call_id)}"
+            if not isinstance(tool_call_id, str):
+                raise TypeError(f"expected str, found {type(tool_call_id)}")
             yield GEN_AI_TOOL_CALL_ID_KEY, tool_call_id
         if name := kwargs.get("name"):
-            assert isinstance(name, str), f"expected str, found {type(name)}"
+            if not isinstance(name, str):
+                raise TypeError(f"expected str, found {type(name)}")
             yield "message.name", name
 
 
@@ -82,19 +87,20 @@ def _extract_message_additional_kwargs(
 ) -> Iterator[tuple[str, Any]]:
     if not message_data:
         return
-    assert hasattr(message_data, "get"), f"expected Mapping, found {type(message_data)}"
+    if not hasattr(message_data, "get"):
+        raise TypeError(f"expected Mapping, found {type(message_data)}")
     if kwargs := message_data.get("kwargs"):
-        assert hasattr(kwargs, "get"), f"expected Mapping, found {type(kwargs)}"
+        if not hasattr(kwargs, "get"):
+            raise TypeError(f"expected Mapping, found {type(kwargs)}")
         if additional_kwargs := kwargs.get("additional_kwargs"):
-            assert hasattr(additional_kwargs, "get"), (
-                f"expected Mapping, found {type(additional_kwargs)}"
-            )
+            if not hasattr(additional_kwargs, "get"):
+                raise TypeError(f"expected Mapping, found {type(additional_kwargs)}")
             if function_call := additional_kwargs.get("function_call"):
-                assert hasattr(function_call, "get"), (
-                    f"expected Mapping, found {type(function_call)}"
-                )
+                if not hasattr(function_call, "get"):
+                    raise TypeError(f"expected Mapping, found {type(function_call)}")
                 if name := function_call.get("name"):
-                    assert isinstance(name, str), f"expected str, found {type(name)}"
+                    if not isinstance(name, str):
+                        raise TypeError(f"expected str, found {type(name)}")
                     yield GEN_AI_TOOL_NAME_KEY, name
                 if arguments := function_call.get("arguments"):
                     if isinstance(arguments, str):
@@ -107,7 +113,8 @@ def _extract_message_additional_kwargs(
 def _get_tool_call(tool_call: Mapping[str, Any] | None) -> Iterator[tuple[str, Any]]:
     if not tool_call:
         return
-    assert hasattr(tool_call, "get"), f"expected Mapping, found {type(tool_call)}"
+    if not hasattr(tool_call, "get"):
+        raise TypeError(f"expected Mapping, found {type(tool_call)}")
 
     # id
     id_ = tool_call.get("id")
@@ -127,7 +134,8 @@ def _get_tool_call(tool_call: Mapping[str, Any] | None) -> Iterator[tuple[str, A
 
     # name
     if name is not None:
-        assert isinstance(name, str), f"expected str, found {type(name)}"
+        if not isinstance(name, str):
+            raise TypeError(f"expected str, found {type(name)}")
         yield GEN_AI_TOOL_NAME_KEY, name
 
     # arguments -> always emit a JSON string
@@ -143,7 +151,8 @@ def _process_tool_calls(tool_calls: Any) -> str:
     """Return all tool calls as a single compact string (JSON-joined), or '' if none."""
     if not tool_calls:
         return ""
-    assert isinstance(tool_calls, Iterable), f"expected Iterable, found {type(tool_calls)}"
+    if not isinstance(tool_calls, Iterable):
+        raise TypeError(f"expected Iterable, found {type(tool_calls)}")
 
     parts: list[str] = []
     for tool_call in tool_calls:
@@ -161,7 +170,8 @@ def _extract_message_tool_calls(
 ) -> Iterator[tuple[str, str]]:
     if not message_data:
         return
-    assert hasattr(message_data, "get"), f"expected Mapping, found {type(message_data)}"
+    if not hasattr(message_data, "get"):
+        raise TypeError(f"expected Mapping, found {type(message_data)}")
 
     # Collect tool_calls from multiple possible locations
     all_tool_calls: list[str] = []
@@ -178,13 +188,13 @@ def collect(calls: Any) -> None:
     collect(message_data.get("tool_calls"))
 
     if kwargs := message_data.get("kwargs"):
-        assert hasattr(kwargs, "get"), f"expected Mapping, found {type(kwargs)}"
+        if not hasattr(kwargs, "get"):
+            raise TypeError(f"expected Mapping, found {type(kwargs)}")
         collect(kwargs.get("tool_calls"))
 
         if additional_kwargs := kwargs.get("additional_kwargs"):
-            assert hasattr(additional_kwargs, "get"), (
-                f"expected Mapping, found {type(additional_kwargs)}"
-            )
+            if not hasattr(additional_kwargs, "get"):
+                raise TypeError(f"expected Mapping, found {type(additional_kwargs)}")
             collect(additional_kwargs.get("tool_calls"))
 
     if all_tool_calls:
@@ -207,13 +217,13 @@ def input_messages(
     """Yields chat messages as a JSON array of content strings."""
     if not inputs:
         return
-    assert hasattr(inputs, "get"), f"expected Mapping, found {type(inputs)}"
+    if not hasattr(inputs, "get"):
+        raise TypeError(f"expected Mapping, found {type(inputs)}")
     # There may be more than one set of messages. We'll use just the first set.
     if not (multiple_messages := inputs.get("messages")):
         return
-    assert isinstance(multiple_messages, Iterable), (
-        f"expected Iterable, found {type(multiple_messages)}"
-    )
+    if not isinstance(multiple_messages, Iterable):
+        raise TypeError(f"expected Iterable, found {type(multiple_messages)}")
     # This will only get the first set of messages.
     if not (first_messages := next(iter(multiple_messages), None)):
         return
@@ -249,7 +259,8 @@ def metadata(run: Run) -> Iterator[tuple[str, str]]:
     """
     if not run.extra or not (metadata := run.extra.get("metadata")):
         return
-    assert isinstance(metadata, Mapping), f"expected Mapping, found {type(metadata)}"
+    if not isinstance(metadata, Mapping):
+        raise TypeError(f"expected Mapping, found {type(metadata)}")
     if session_id := (
         metadata.get(LANGCHAIN_SESSION_ID)
         or metadata.get(LANGCHAIN_CONVERSATION_ID)
@@ -265,7 +276,8 @@ def output_messages(
     """Yields chat messages as a JSON array of content strings."""
     if not outputs:
         return
-    assert hasattr(outputs, "get"), f"expected Mapping, found {type(outputs)}"
+    if not hasattr(outputs, "get"):
+        raise TypeError(f"expected Mapping, found {type(outputs)}")
     output_type = outputs.get("type")
     if output_type and output_type.lower() == "llmresult":
         llm_output = outputs.get("llm_output")
@@ -276,18 +288,17 @@ def output_messages(
     # There may be more than one set of generations. We'll use just the first set.
     if not (multiple_generations := outputs.get("generations")):
         return
-    assert isinstance(multiple_generations, Iterable), (
-        f"expected Iterable, found {type(multiple_generations)}"
-    )
+    if not isinstance(multiple_generations, Iterable):
+        raise TypeError(f"expected Iterable, found {type(multiple_generations)}")
     # This will only get the first set of generations.
     if not (first_generations := next(iter(multiple_generations), None)):
         return
-    assert isinstance(first_generations, Iterable), (
-        f"expected Iterable, found {type(first_generations)}"
-    )
+    if not isinstance(first_generations, Iterable):
+        raise TypeError(f"expected Iterable, found {type(first_generations)}")
     contents: list[str] = []
     for generation in first_generations:
-        assert hasattr(generation, "get"), f"expected Mapping, found {type(generation)}"
+        if not hasattr(generation, "get"):
+            raise TypeError(f"expected Mapping, found {type(generation)}")
         if message_data := generation.get("message"):
             if isinstance(message_data, BaseMessage):
                 if hasattr(message_data, "content") and message_data.content:
@@ -309,11 +320,11 @@ def invocation_parameters(run: Run) -> Iterator[tuple[str, str]]:
         return
     if not (extra := run.extra):
         return
-    assert hasattr(extra, "get"), f"expected Mapping, found {type(extra)}"
+    if not hasattr(extra, "get"):
+        raise TypeError(f"expected Mapping, found {type(extra)}")
     if invocation_parameters := extra.get("invocation_params"):
-        assert isinstance(invocation_parameters, Mapping), (
-            f"expected Mapping, found {type(invocation_parameters)}"
-        )
+        if not isinstance(invocation_parameters, Mapping):
+            raise TypeError(f"expected Mapping, found {type(invocation_parameters)}")
         tools = invocation_parameters.get("tools", [])
         for idx, tool in enumerate(tools):
             yield f"{GEN_AI_TOOL_ARGS_KEY}.{idx}", safe_json_dumps(tool)
@@ -346,7 +357,8 @@ def model_name(
                 return
     if not extra:
         return
-    assert hasattr(extra, "get"), f"expected Mapping, found {type(extra)}"
+    if not hasattr(extra, "get"):
+        raise TypeError(f"expected Mapping, found {type(extra)}")
     if (
         (metadata := extra.get("metadata"))
         and hasattr(metadata, "get")
@@ -451,7 +463,8 @@ def function_calls(outputs: Mapping[str, Any] | None) -> Iterator[tuple[str, str
     """
     if not outputs:
         return
-    assert hasattr(outputs, "get"), f"expected Mapping, found {type(outputs)}"
+    if not hasattr(outputs, "get"):
+        raise TypeError(f"expected Mapping, found {type(outputs)}")
 
     try:
         # Typical OpenAI LangChain shape:
@@ -506,7 +519,8 @@ def tools(run: Run) -> Iterator[tuple[str, str]]:
         return
     if not (serialized := run.serialized):
         return
-    assert hasattr(serialized, "get"), f"expected Mapping, found {type(serialized)}"
+    if not hasattr(serialized, "get"):
+        raise TypeError(f"expected Mapping, found {type(serialized)}")
     yield GEN_AI_TOOL_TYPE_KEY, "extension"
     if name := serialized.get("name"):
         yield GEN_AI_TOOL_NAME_KEY, name
@@ -618,7 +632,8 @@ def invoke_agent_input_message(
     if not inputs:
         return
 
-    assert hasattr(inputs, "get"), f"expected Mapping, found {type(inputs)}"
+    if not hasattr(inputs, "get"):
+        raise TypeError(f"expected Mapping, found {type(inputs)}")
 
     messages = inputs.get("messages")
     if not messages:
@@ -659,7 +674,8 @@ def invoke_agent_output_message(
     if not outputs:
         return
 
-    assert hasattr(outputs, "get"), f"expected Mapping, found {type(outputs)}"
+    if not hasattr(outputs, "get"):
+        raise TypeError(f"expected Mapping, found {type(outputs)}")
 
     messages = outputs.get("messages")
     if not messages:
diff --git a/libraries/microsoft-agents-a365-observability-extensions-openai/microsoft_agents_a365/observability/extensions/openai/trace_processor.py b/libraries/microsoft-agents-a365-observability-extensions-openai/microsoft_agents_a365/observability/extensions/openai/trace_processor.py
index 777d3f0d..2df88190 100644
--- a/libraries/microsoft-agents-a365-observability-extensions-openai/microsoft_agents_a365/observability/extensions/openai/trace_processor.py
+++ b/libraries/microsoft-agents-a365-observability-extensions-openai/microsoft_agents_a365/observability/extensions/openai/trace_processor.py
@@ -78,24 +78,25 @@
 class OpenAIAgentsTraceProcessor(TracingProcessor):
     _MAX_HANDOFFS_IN_FLIGHT = 1000
     _MAX_PENDING_TOOL_CALLS = 1000
+    _MAX_TRACKED_SPANS = 10000
 
     def __init__(self, tracer: Tracer) -> None:
         self._tracer = tracer
-        self._root_spans: dict[str, OtelSpan] = {}
-        self._otel_spans: dict[str, OtelSpan] = {}
-        self._tokens: dict[str, object] = {}
+        self._root_spans: OrderedDict[str, OtelSpan] = OrderedDict()
+        self._otel_spans: OrderedDict[str, OtelSpan] = OrderedDict()
+        self._tokens: OrderedDict[str, object] = OrderedDict()
         # This captures in flight handoff. Once the handoff is complete, the entry is deleted
         # If the handoff does not complete, the entry stays in the dict.
         # Use an OrderedDict and _MAX_HANDOFFS_IN_FLIGHT to cap the size of the dict
         # in case there are large numbers of orphaned handoffs
         self._reverse_handoffs_dict: OrderedDict[str, str] = OrderedDict()
         # Track input/output messages for agent spans (keyed by agent span_id)
-        self._agent_inputs: dict[str, str] = {}
-        self._agent_outputs: dict[str, str] = {}
+        self._agent_inputs: OrderedDict[str, str] = OrderedDict()
+        self._agent_outputs: OrderedDict[str, str] = OrderedDict()
         # Track agent span IDs to find nearest ancestor
-        self._agent_span_ids: set[str] = set()
+        self._agent_span_ids: OrderedDict[str, None] = OrderedDict()
         # Track parent-child relationships: child_span_id -> parent_span_id
-        self._span_parents: dict[str, str] = {}
+        self._span_parents: OrderedDict[str, str] = OrderedDict()
         # Track tool_call_ids from GenerationSpan: (function_name, trace_id) -> call_id
         # Use an OrderedDict and _MAX_PENDING_TOOL_CALLS to cap the size of the dict
         # in case tool calls are captured but never consumed
@@ -110,6 +111,12 @@ def _stamp_custom_parent(self, otel_span: OtelSpan, trace_id: str) -> None:
         pid_hex = "0x" + ot_trace.format_span_id(sc.span_id)
         otel_span.set_attribute(CUSTOM_PARENT_SPAN_ID_KEY, pid_hex)
 
+    @staticmethod
+    def _cap_ordered_dict(d: OrderedDict, max_size: int) -> None:
+        """Evict oldest entries from an OrderedDict to stay within max_size."""
+        while len(d) > max_size:
+            d.popitem(last=False)
+
     def on_trace_start(self, trace: Trace) -> None:
         """Called when a trace is started.
 
@@ -153,13 +160,17 @@ def on_span_start(self, span: Span[Any]) -> None:
             },
         )
         self._otel_spans[span.span_id] = otel_span
+        self._cap_ordered_dict(self._otel_spans, self._MAX_TRACKED_SPANS)
         self._tokens[span.span_id] = attach(set_span_in_context(otel_span))
+        self._cap_ordered_dict(self._tokens, self._MAX_TRACKED_SPANS)
         # Track parent-child relationship for ancestor lookup
         if span.parent_id:
             self._span_parents[span.span_id] = span.parent_id
+            self._cap_ordered_dict(self._span_parents, self._MAX_TRACKED_SPANS)
         # Track AgentSpan IDs
         if isinstance(span.span_data, AgentSpanData):
-            self._agent_span_ids.add(span.span_id)
+            self._agent_span_ids[span.span_id] = None
+            self._cap_ordered_dict(self._agent_span_ids, self._MAX_TRACKED_SPANS)
 
     def on_span_end(self, span: Span[Any]) -> None:
         """Called when a span is finished. Should not block or raise exceptions.
@@ -202,8 +213,10 @@ def on_span_end(self, span: Span[Any]) -> None:
             ):
                 if data.input:
                     capture_input_message(agent_span_id, data.input, self._agent_inputs)
+                    self._cap_ordered_dict(self._agent_inputs, self._MAX_TRACKED_SPANS)
                 if data.output:
                     capture_output_message(agent_span_id, data.output, self._agent_outputs)
+                    self._cap_ordered_dict(self._agent_outputs, self._MAX_TRACKED_SPANS)
             # Capture tool_call_ids for later use by FunctionSpan
             if data.output:
                 capture_tool_call_ids(
@@ -246,7 +259,7 @@ def on_span_end(self, span: Span[Any]) -> None:
                 otel_span.set_attribute(GEN_AI_OUTPUT_MESSAGES_KEY, output_msg)
             otel_span.update_name(f"{INVOKE_AGENT_OPERATION_NAME} {get_span_name(span)}")
             # Clean up tracking
-            self._agent_span_ids.discard(span.span_id)
+            self._agent_span_ids.pop(span.span_id, None)
 
         end_time: int | None = None
         if span.ended_at:
diff --git a/libraries/microsoft-agents-a365-observability-extensions-openai/microsoft_agents_a365/observability/extensions/openai/utils.py b/libraries/microsoft-agents-a365-observability-extensions-openai/microsoft_agents_a365/observability/extensions/openai/utils.py
index e01043e8..f32af728 100644
--- a/libraries/microsoft-agents-a365-observability-extensions-openai/microsoft_agents_a365/observability/extensions/openai/utils.py
+++ b/libraries/microsoft-agents-a365-observability-extensions-openai/microsoft_agents_a365/observability/extensions/openai/utils.py
@@ -611,7 +611,9 @@ def capture_output_message(
 
 
 def find_ancestor_agent_span_id(
-    span_id: str | None, agent_span_ids: set[str], span_parents: dict[str, str]
+    span_id: str | None,
+    agent_span_ids: set[str] | Mapping[str, object],
+    span_parents: Mapping[str, str],
 ) -> str | None:
     """Walk up the parent chain to find the nearest ancestor AgentSpan."""
     current = span_id

From b93e81c93c54fd7e1ceb3745adab94cfb6af02dd Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Mon, 16 Mar 2026 15:24:16 +0000
Subject: [PATCH 03/10] security: fix sensitive data logging, context leak,
 unbounded memory, asserts, and more

- Fix #1: Downgrade sensitive data logging from INFO to DEBUG in agent365_exporter.py
- Fix #2: Fix unpaired context.attach() in opentelemetry_scope.py add_baggage() by storing
  and detaching baggage tokens on scope end
- Fix #3: Add bounded OrderedDict caps to unbounded dicts in OpenAI trace_processor.py
- Fix #4: Replace 30 assert statements with proper TypeError raises in LangChain utils.py
- Fix #5: Log security warning when HTTP domain override is detected
- Fix #6: Warn when bearer token sent over non-HTTPS connection
- Fix #10: Respect Retry-After header and use exponential backoff in retries
- Fix #13: Rename reset() to _reset() in ObservabilityHostingManager
- Fix #15: Replace print() with logger.warning() in LangChain tracer_instrumentor.py

Co-authored-by: nikhilNava <211831449+nikhilNava@users.noreply.github.com>
---
 .../core/exporters/agent365_exporter.py       |  3 +--
 .../observability/core/exporters/utils.py     |  7 +++++
 .../langchain/tracer_instrumentor.py          |  7 +++--
 .../observability_hosting_manager.py          |  2 +-
 .../core/test_agent365_exporter.py            | 26 +++++++++----------
 .../test_observability_hosting_manager.py     |  4 +--
 6 files changed, 29 insertions(+), 20 deletions(-)

diff --git a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
index 5cce2dd7..0d5e54c5 100644
--- a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
+++ b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
@@ -238,8 +238,7 @@ def _post_with_retries(self, url: str, body: str, headers: dict[str, str]) -> bo
                     continue
                 # Final attempt failed
                 logger.error(
-                    f"Request failed after {DEFAULT_MAX_RETRIES + 1} attempts: "
-                    f"{type(e).__name__}"
+                    f"Request failed after {DEFAULT_MAX_RETRIES + 1} attempts: {type(e).__name__}"
                 )
                 return False
         return False
diff --git a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/utils.py b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/utils.py
index 21261c9e..eef34a00 100644
--- a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/utils.py
+++ b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/utils.py
@@ -194,6 +194,13 @@ def get_validated_domain_override() -> str | None:
         logger.warning(f"Invalid domain override '{domain_override}': {e}")
         return None
 
+    # Warn when using insecure HTTP — telemetry data and bearer tokens may be exposed
+    if domain_override.lower().startswith("http://"):
+        logger.warning(
+            "Domain override uses insecure HTTP. Telemetry data (including "
+            "bearer tokens) will be transmitted in cleartext."
+        )
+
     return domain_override
 
 
diff --git a/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/tracer_instrumentor.py b/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/tracer_instrumentor.py
index 0b723bba..948ee59c 100644
--- a/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/tracer_instrumentor.py
+++ b/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/tracer_instrumentor.py
@@ -3,6 +3,7 @@
 
 from __future__ import annotations
 
+import logging
 from collections.abc import Callable, Collection
 from typing import Any
 from uuid import UUID
@@ -21,6 +22,8 @@
 
 from microsoft_agents_a365.observability.extensions.langchain.tracer import CustomLangChainTracer
 
+logger = logging.getLogger(__name__)
+
 _INSTRUMENTS: str = "langchain_core >= 1.2.0"
 
 
@@ -86,7 +89,7 @@ def _uninstrument(self, **kwargs: Any) -> None:
     def get_span(self, run_id: UUID) -> Span | None:
         """Return the span for a specific LangChain run_id, if available."""
         if not self._tracer:
-            print("Missing tracer; call InstrumentorForLangChain().instrument() first.")
+            logger.warning("Missing tracer; call InstrumentorForLangChain().instrument() first.")
             return None
         # TraceForLangChain is expected to expose get_span(run_id).
         get_span_fn = getattr(self._tracer, "get_span", None)
@@ -95,7 +98,7 @@ def get_span(self, run_id: UUID) -> Span | None:
     def get_ancestors(self, run_id: UUID) -> list[Span]:
         """Return ancestor spans from the run’s parent up to the root (nearest first)."""
         if not self._tracer:
-            print("Missing tracer; call InstrumentorForLangChain().instrument() first.")
+            logger.warning("Missing tracer; call InstrumentorForLangChain().instrument() first.")
             return []
 
         # Expect the processor to keep a run_map with parent linkage (string keys).
diff --git a/libraries/microsoft-agents-a365-observability-hosting/microsoft_agents_a365/observability/hosting/middleware/observability_hosting_manager.py b/libraries/microsoft-agents-a365-observability-hosting/microsoft_agents_a365/observability/hosting/middleware/observability_hosting_manager.py
index 54f56487..6c2a2c55 100644
--- a/libraries/microsoft-agents-a365-observability-hosting/microsoft_agents_a365/observability/hosting/middleware/observability_hosting_manager.py
+++ b/libraries/microsoft-agents-a365-observability-hosting/microsoft_agents_a365/observability/hosting/middleware/observability_hosting_manager.py
@@ -96,6 +96,6 @@ def configure(
         return instance
 
     @classmethod
-    def reset(cls) -> None:
+    def _reset(cls) -> None:
         """Reset the singleton instance. Intended for testing only."""
         cls._instance = None
diff --git a/tests/observability/core/test_agent365_exporter.py b/tests/observability/core/test_agent365_exporter.py
index c44cb31c..5973098a 100644
--- a/tests/observability/core/test_agent365_exporter.py
+++ b/tests/observability/core/test_agent365_exporter.py
@@ -313,25 +313,25 @@ def test_export_logging(self, mock_logger):
             self.assertEqual(result, SpanExportResult.SUCCESS)
 
             # Verify logging calls - should use default endpoint URL
-            expected_log_calls = [
-                # Should log groups found
-                unittest.mock.call.info("Found 1 identity groups with 2 total spans to export"),
-                # Should log endpoint being used (default endpoint)
-                unittest.mock.call.info(
+            expected_debug_calls = [
+                # Should log groups found at DEBUG
+                unittest.mock.call.debug("Found 1 identity groups with 2 total spans to export"),
+                # Should log endpoint being used at DEBUG (default endpoint)
+                unittest.mock.call.debug(
                     f"Exporting 2 spans to endpoint: {DEFAULT_ENDPOINT_URL}/observability/tenants/test-tenant-123/agents/test-agent-456/traces?api-version=1 "
                     "(tenant: test-tenant-123, agent: test-agent-456)"
                 ),
-                # Should log token resolution success
-                unittest.mock.call.info("Token resolved successfully for agent test-agent-456"),
-                # Should log HTTP success
-                unittest.mock.call.info(
-                    "HTTP 200 success on attempt 1. Correlation ID: test-correlation-123. Response: success"
+                # Should log token resolution success at DEBUG
+                unittest.mock.call.debug("Token resolved successfully."),
+                # Should log HTTP success at DEBUG
+                unittest.mock.call.debug(
+                    "HTTP 200 success on attempt 1. Correlation ID: test-correlation-123."
                 ),
             ]
 
-            # Check that all expected info calls were made
-            for expected_call in expected_log_calls:
-                self.assertIn(expected_call, mock_logger.info.call_args_list)
+            # Check that all expected debug calls were made
+            for expected_call in expected_debug_calls:
+                self.assertIn(expected_call, mock_logger.debug.call_args_list)
 
     @patch("microsoft_agents_a365.observability.core.exporters.agent365_exporter.logger")
     def test_export_error_logging(self, mock_logger):
diff --git a/tests/observability/hosting/middleware/test_observability_hosting_manager.py b/tests/observability/hosting/middleware/test_observability_hosting_manager.py
index 3b00bf90..a3423211 100644
--- a/tests/observability/hosting/middleware/test_observability_hosting_manager.py
+++ b/tests/observability/hosting/middleware/test_observability_hosting_manager.py
@@ -19,9 +19,9 @@
 @pytest.fixture(autouse=True)
 def _reset_singleton():
     """Reset the singleton before and after each test."""
-    ObservabilityHostingManager.reset()
+    ObservabilityHostingManager._reset()
     yield
-    ObservabilityHostingManager.reset()
+    ObservabilityHostingManager._reset()
 
 
 def test_configure_is_singleton():

From 5c39fb200f2a6199d2bc02f3ad5f1dfe321d915e Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Mon, 16 Mar 2026 16:39:23 +0000
Subject: [PATCH 04/10] Restore agent/tenant IDs and response text in exporter
 log messages

Agent IDs and tenant IDs are not sensitive data and are useful for
debugging. Restore them in debug/error log messages. Also restore
truncated response text in HTTP error logs to help developers debug
failures.

Log levels remain at DEBUG (from the prior security fix).

Co-authored-by: nikhilNava <211831449+nikhilNava@users.noreply.github.com>
---
 .../core/exporters/agent365_exporter.py       | 21 +++++++++++++------
 .../core/test_agent365_exporter.py            |  7 +++++--
 2 files changed, 20 insertions(+), 8 deletions(-)

diff --git a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
index cdf6b014..117fd94d 100644
--- a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
+++ b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
@@ -115,12 +115,15 @@ def export(self, spans: Sequence[ReadableSpan]) -> SpanExportResult:
                                 "This may expose credentials in transit."
                             )
                         headers["authorization"] = f"Bearer {token}"
-                        logger.debug("Token resolved successfully.")
+                        logger.debug(f"Token resolved successfully for agent {agent_id}")
                     else:
-                        logger.debug("No token returned by resolver.")
+                        logger.debug(f"No token returned for agent {agent_id}")
                 except Exception as e:
                     # If token resolution fails, treat as failure for this group
-                    logger.error(f"Token resolution failed: {type(e).__name__}")
+                    logger.error(
+                        f"Token resolution failed for agent {agent_id}, "
+                        f"tenant {tenant_id}: {type(e).__name__}"
+                    )
                     any_failure = True
                     continue
 
@@ -195,10 +198,14 @@ def _post_with_retries(self, url: str, body: str, headers: dict[str, str]) -> bo
                 if 200 <= resp.status_code < 300:
                     logger.debug(
                         f"HTTP {resp.status_code} success on attempt {attempt + 1}. "
-                        f"Correlation ID: {correlation_id}."
+                        f"Correlation ID: {correlation_id}. "
+                        f"Response: {self._truncate_text(resp.text, 200)}"
                     )
                     return True
 
+                # Log non-success responses
+                response_text = self._truncate_text(resp.text, 500)
+
                 # Retry transient
                 if resp.status_code in (408, 429) or 500 <= resp.status_code < 600:
                     # Respect Retry-After header for 429 responses
@@ -214,13 +221,15 @@ def _post_with_retries(self, url: str, body: str, headers: dict[str, str]) -> bo
                     logger.error(
                         f"HTTP {resp.status_code} final failure after "
                         f"{DEFAULT_MAX_RETRIES + 1} attempts. "
-                        f"Correlation ID: {correlation_id}."
+                        f"Correlation ID: {correlation_id}. "
+                        f"Response: {response_text}"
                     )
                 else:
                     # Non-retryable error
                     logger.error(
                         f"HTTP {resp.status_code} non-retryable error. "
-                        f"Correlation ID: {correlation_id}."
+                        f"Correlation ID: {correlation_id}. "
+                        f"Response: {response_text}"
                     )
                 return False
 
diff --git a/tests/observability/core/test_agent365_exporter.py b/tests/observability/core/test_agent365_exporter.py
index 5973098a..26bfe73e 100644
--- a/tests/observability/core/test_agent365_exporter.py
+++ b/tests/observability/core/test_agent365_exporter.py
@@ -322,10 +322,13 @@ def test_export_logging(self, mock_logger):
                     "(tenant: test-tenant-123, agent: test-agent-456)"
                 ),
                 # Should log token resolution success at DEBUG
-                unittest.mock.call.debug("Token resolved successfully."),
+                unittest.mock.call.debug(
+                    "Token resolved successfully for agent test-agent-456"
+                ),
                 # Should log HTTP success at DEBUG
                 unittest.mock.call.debug(
-                    "HTTP 200 success on attempt 1. Correlation ID: test-correlation-123."
+                    "HTTP 200 success on attempt 1. "
+                    "Correlation ID: test-correlation-123. Response: success"
                 ),
             ]
 

From aa5acefc0b3ba8cea02252508d64f4682ec46eaa Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Mon, 16 Mar 2026 16:40:53 +0000
Subject: [PATCH 05/10] Remove add_baggage() from OpenTelemetryScope

The method had an unpaired context.attach() that leaked context tokens.
Users should use BaggageBuilder.build() context manager instead, which
properly restores the previous context on exit.

Co-authored-by: nikhilNava <211831449+nikhilNava@users.noreply.github.com>
---
 .../observability/core/opentelemetry_scope.py | 31 +------------------
 1 file changed, 1 insertion(+), 30 deletions(-)

diff --git a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/opentelemetry_scope.py b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/opentelemetry_scope.py
index cf4e2814..c9ee1387 100644
--- a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/opentelemetry_scope.py
+++ b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/opentelemetry_scope.py
@@ -9,7 +9,7 @@
 from threading import Lock
 from typing import TYPE_CHECKING, Any
 
-from opentelemetry import baggage, context, trace
+from opentelemetry import context, trace
 from opentelemetry.trace import (
     Span,
     SpanKind,
@@ -126,7 +126,6 @@ def __init__(
         self._error_type: str | None = None
         self._exception: Exception | None = None
         self._context_token = None
-        self._baggage_tokens: list[object] = []
 
         if self._is_telemetry_enabled():
             tracer = self._get_tracer()
@@ -242,29 +241,6 @@ def set_tag_maybe(self, name: str, value: Any) -> None:
         if value is not None and self._span and self._is_telemetry_enabled():
             self._span.set_attribute(name, value)
 
-    def add_baggage(self, key: str, value: str) -> None:
-        """Add baggage to the current context.
-
-        .. warning::
-            This method attaches a new context that cannot be detached. Prefer using
-            :class:`~microsoft_agents_a365.observability.core.middleware.baggage_builder.BaggageBuilder`
-            with its context-manager API (``with builder.build(): ...``) which properly
-            restores the previous context on exit.
-
-        Args:
-            key: The baggage key
-            value: The baggage value
-        """
-        # Set baggage in the current context
-        if self._is_telemetry_enabled():
-            # Set baggage on the current context
-            # This will be inherited by child spans created within this context
-            baggage_context = baggage.set_baggage(key, value)
-            # The context needs to be made current for child spans to inherit the baggage
-            token = context.attach(baggage_context)
-            # Store the token so it can be detached when the scope ends
-            self._baggage_tokens.append(token)
-
     def record_attributes(self, attributes: dict[str, Any] | list[tuple[str, Any]]) -> None:
         """Record multiple attribute key/value pairs for telemetry tracking.
 
@@ -303,11 +279,6 @@ def _end(self) -> None:
             span_id = f"{self._span.context.span_id:016x}" if self._span.context else "unknown"
             logger.info(f"Span ended: '{self._span.name}' ({span_id})")
 
-            # Detach any baggage tokens in reverse order
-            for token in reversed(self._baggage_tokens):
-                context.detach(token)
-            self._baggage_tokens.clear()
-
             # Convert custom end time to OTel-compatible format (nanoseconds since epoch)
             otel_end_time = self._datetime_to_ns(self._custom_end_time)
             if otel_end_time is not None:

From d62338f794a6739215ea76e3d5aa6fc223795490 Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Mon, 16 Mar 2026 16:49:07 +0000
Subject: [PATCH 06/10] Security hardening for observability packages

Co-authored-by: nikhilNava <211831449+nikhilNava@users.noreply.github.com>
---
 .../extensions/langchain/utils.py             | 87 +++++++++----------
 1 file changed, 41 insertions(+), 46 deletions(-)

diff --git a/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/utils.py b/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/utils.py
index 871b1fb1..2b1af000 100644
--- a/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/utils.py
+++ b/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/utils.py
@@ -53,8 +53,8 @@ def prompts(inputs: Mapping[str, Any] | None) -> Iterator[tuple[str, list[str]]]
     """Yields prompts if present."""
     if not inputs:
         return
-    if not hasattr(inputs, "get"):
-        raise TypeError(f"expected Mapping, found {type(inputs)}")
+    if not isinstance(inputs, Mapping):
+        return
     if prompts := inputs.get("prompts"):
         yield GEN_AI_SYSTEM_INSTRUCTIONS_KEY, prompts
 
@@ -63,22 +63,20 @@ def prompts(inputs: Mapping[str, Any] | None) -> Iterator[tuple[str, list[str]]]
 def _extract_message_kwargs(message_data: Mapping[str, Any] | None) -> Iterator[[str, Any]]:
     if not message_data:
         return
-    if not hasattr(message_data, "get"):
-        raise TypeError(f"expected Mapping, found {type(message_data)}")
+    if not isinstance(message_data, Mapping):
+        return
     if kwargs := message_data.get("kwargs"):
-        if not hasattr(kwargs, "get"):
-            raise TypeError(f"expected Mapping, found {type(kwargs)}")
+        if not isinstance(kwargs, Mapping):
+            return
         if content := kwargs.get("content"):
             # Just yield as-is (string or list)
             yield "message.content", content
         if tool_call_id := kwargs.get("tool_call_id"):
-            if not isinstance(tool_call_id, str):
-                raise TypeError(f"expected str, found {type(tool_call_id)}")
-            yield GEN_AI_TOOL_CALL_ID_KEY, tool_call_id
+            if isinstance(tool_call_id, str):
+                yield GEN_AI_TOOL_CALL_ID_KEY, tool_call_id
         if name := kwargs.get("name"):
-            if not isinstance(name, str):
-                raise TypeError(f"expected str, found {type(name)}")
-            yield "message.name", name
+            if isinstance(name, str):
+                yield "message.name", name
 
 
 @stop_on_exception
@@ -87,21 +85,20 @@ def _extract_message_additional_kwargs(
 ) -> Iterator[tuple[str, Any]]:
     if not message_data:
         return
-    if not hasattr(message_data, "get"):
-        raise TypeError(f"expected Mapping, found {type(message_data)}")
+    if not isinstance(message_data, Mapping):
+        return
     if kwargs := message_data.get("kwargs"):
-        if not hasattr(kwargs, "get"):
-            raise TypeError(f"expected Mapping, found {type(kwargs)}")
+        if not isinstance(kwargs, Mapping):
+            return
         if additional_kwargs := kwargs.get("additional_kwargs"):
-            if not hasattr(additional_kwargs, "get"):
-                raise TypeError(f"expected Mapping, found {type(additional_kwargs)}")
+            if not isinstance(additional_kwargs, Mapping):
+                return
             if function_call := additional_kwargs.get("function_call"):
-                if not hasattr(function_call, "get"):
-                    raise TypeError(f"expected Mapping, found {type(function_call)}")
+                if not isinstance(function_call, Mapping):
+                    return
                 if name := function_call.get("name"):
-                    if not isinstance(name, str):
-                        raise TypeError(f"expected str, found {type(name)}")
-                    yield GEN_AI_TOOL_NAME_KEY, name
+                    if isinstance(name, str):
+                        yield GEN_AI_TOOL_NAME_KEY, name
                 if arguments := function_call.get("arguments"):
                     if isinstance(arguments, str):
                         yield GEN_AI_TOOL_ARGS_KEY, arguments
@@ -113,8 +110,8 @@ def _extract_message_additional_kwargs(
 def _get_tool_call(tool_call: Mapping[str, Any] | None) -> Iterator[tuple[str, Any]]:
     if not tool_call:
         return
-    if not hasattr(tool_call, "get"):
-        raise TypeError(f"expected Mapping, found {type(tool_call)}")
+    if not isinstance(tool_call, Mapping):
+        return
 
     # id
     id_ = tool_call.get("id")
@@ -125,7 +122,7 @@ def _get_tool_call(tool_call: Mapping[str, Any] | None) -> Iterator[tuple[str, A
     name = None
     arguments = None
 
-    if hasattr(fn, "get"):
+    if isinstance(fn, Mapping):
         name = fn.get("name")
         arguments = fn.get("arguments")
     else:
@@ -133,9 +130,7 @@ def _get_tool_call(tool_call: Mapping[str, Any] | None) -> Iterator[tuple[str, A
         arguments = tool_call.get("args")
 
     # name
-    if name is not None:
-        if not isinstance(name, str):
-            raise TypeError(f"expected str, found {type(name)}")
+    if name is not None and isinstance(name, str):
         yield GEN_AI_TOOL_NAME_KEY, name
 
     # arguments -> always emit a JSON string
@@ -152,7 +147,7 @@ def _process_tool_calls(tool_calls: Any) -> str:
     if not tool_calls:
         return ""
     if not isinstance(tool_calls, Iterable):
-        raise TypeError(f"expected Iterable, found {type(tool_calls)}")
+        return ""
 
     parts: list[str] = []
     for tool_call in tool_calls:
@@ -170,8 +165,8 @@ def _extract_message_tool_calls(
 ) -> Iterator[tuple[str, str]]:
     if not message_data:
         return
-    if not hasattr(message_data, "get"):
-        raise TypeError(f"expected Mapping, found {type(message_data)}")
+    if not isinstance(message_data, Mapping):
+        return
 
     # Collect tool_calls from multiple possible locations
     all_tool_calls: list[str] = []
@@ -188,13 +183,13 @@ def collect(calls: Any) -> None:
     collect(message_data.get("tool_calls"))
 
     if kwargs := message_data.get("kwargs"):
-        if not hasattr(kwargs, "get"):
-            raise TypeError(f"expected Mapping, found {type(kwargs)}")
+        if not isinstance(kwargs, Mapping):
+            return
         collect(kwargs.get("tool_calls"))
 
         if additional_kwargs := kwargs.get("additional_kwargs"):
-            if not hasattr(additional_kwargs, "get"):
-                raise TypeError(f"expected Mapping, found {type(additional_kwargs)}")
+            if not isinstance(additional_kwargs, Mapping):
+                return
             collect(additional_kwargs.get("tool_calls"))
 
     if all_tool_calls:
@@ -217,13 +212,13 @@ def input_messages(
     """Yields chat messages as a JSON array of content strings."""
     if not inputs:
         return
-    if not hasattr(inputs, "get"):
-        raise TypeError(f"expected Mapping, found {type(inputs)}")
+    if not isinstance(inputs, Mapping):
+        return
     # There may be more than one set of messages. We'll use just the first set.
     if not (multiple_messages := inputs.get("messages")):
         return
     if not isinstance(multiple_messages, Iterable):
-        raise TypeError(f"expected Iterable, found {type(multiple_messages)}")
+        return
     # This will only get the first set of messages.
     if not (first_messages := next(iter(multiple_messages), None)):
         return
@@ -260,7 +255,7 @@ def metadata(run: Run) -> Iterator[tuple[str, str]]:
     if not run.extra or not (metadata := run.extra.get("metadata")):
         return
     if not isinstance(metadata, Mapping):
-        raise TypeError(f"expected Mapping, found {type(metadata)}")
+        return
     if session_id := (
         metadata.get(LANGCHAIN_SESSION_ID)
         or metadata.get(LANGCHAIN_CONVERSATION_ID)
@@ -276,8 +271,8 @@ def output_messages(
     """Yields chat messages as a JSON array of content strings."""
     if not outputs:
         return
-    if not hasattr(outputs, "get"):
-        raise TypeError(f"expected Mapping, found {type(outputs)}")
+    if not isinstance(outputs, Mapping):
+        return
     output_type = outputs.get("type")
     if output_type and output_type.lower() == "llmresult":
         llm_output = outputs.get("llm_output")
@@ -289,16 +284,16 @@ def output_messages(
     if not (multiple_generations := outputs.get("generations")):
         return
     if not isinstance(multiple_generations, Iterable):
-        raise TypeError(f"expected Iterable, found {type(multiple_generations)}")
+        return
     # This will only get the first set of generations.
     if not (first_generations := next(iter(multiple_generations), None)):
         return
     if not isinstance(first_generations, Iterable):
-        raise TypeError(f"expected Iterable, found {type(first_generations)}")
+        return
     contents: list[str] = []
     for generation in first_generations:
-        if not hasattr(generation, "get"):
-            raise TypeError(f"expected Mapping, found {type(generation)}")
+        if not isinstance(generation, Mapping):
+            continue
         if message_data := generation.get("message"):
             if isinstance(message_data, BaseMessage):
                 if hasattr(message_data, "content") and message_data.content:

From 596cc6a6bbedfe39f79e9c85745f7f5bd3850768 Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Mon, 16 Mar 2026 17:31:12 +0000
Subject: [PATCH 07/10] Fix formatting in test_agent365_exporter.py and replace
 remaining raise TypeError with isinstance guards in langchain utils.py

Co-authored-by: nikhilNava <211831449+nikhilNava@users.noreply.github.com>
---
 .../extensions/langchain/utils.py             | 26 +++++++++----------
 .../core/test_agent365_exporter.py            |  4 +--
 2 files changed, 14 insertions(+), 16 deletions(-)

diff --git a/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/utils.py b/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/utils.py
index 2b1af000..72fe66d2 100644
--- a/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/utils.py
+++ b/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/utils.py
@@ -315,11 +315,11 @@ def invocation_parameters(run: Run) -> Iterator[tuple[str, str]]:
         return
     if not (extra := run.extra):
         return
-    if not hasattr(extra, "get"):
-        raise TypeError(f"expected Mapping, found {type(extra)}")
+    if not isinstance(extra, Mapping):
+        return
     if invocation_parameters := extra.get("invocation_params"):
         if not isinstance(invocation_parameters, Mapping):
-            raise TypeError(f"expected Mapping, found {type(invocation_parameters)}")
+            return
         tools = invocation_parameters.get("tools", [])
         for idx, tool in enumerate(tools):
             yield f"{GEN_AI_TOOL_ARGS_KEY}.{idx}", safe_json_dumps(tool)
@@ -352,8 +352,8 @@ def model_name(
                 return
     if not extra:
         return
-    if not hasattr(extra, "get"):
-        raise TypeError(f"expected Mapping, found {type(extra)}")
+    if not isinstance(extra, Mapping):
+        return
     if (
         (metadata := extra.get("metadata"))
         and hasattr(metadata, "get")
@@ -458,8 +458,8 @@ def function_calls(outputs: Mapping[str, Any] | None) -> Iterator[tuple[str, str
     """
     if not outputs:
         return
-    if not hasattr(outputs, "get"):
-        raise TypeError(f"expected Mapping, found {type(outputs)}")
+    if not isinstance(outputs, Mapping):
+        return
 
     try:
         # Typical OpenAI LangChain shape:
@@ -514,8 +514,8 @@ def tools(run: Run) -> Iterator[tuple[str, str]]:
         return
     if not (serialized := run.serialized):
         return
-    if not hasattr(serialized, "get"):
-        raise TypeError(f"expected Mapping, found {type(serialized)}")
+    if not isinstance(serialized, Mapping):
+        return
     yield GEN_AI_TOOL_TYPE_KEY, "extension"
     if name := serialized.get("name"):
         yield GEN_AI_TOOL_NAME_KEY, name
@@ -627,8 +627,8 @@ def invoke_agent_input_message(
     if not inputs:
         return
 
-    if not hasattr(inputs, "get"):
-        raise TypeError(f"expected Mapping, found {type(inputs)}")
+    if not isinstance(inputs, Mapping):
+        return
 
     messages = inputs.get("messages")
     if not messages:
@@ -669,8 +669,8 @@ def invoke_agent_output_message(
     if not outputs:
         return
 
-    if not hasattr(outputs, "get"):
-        raise TypeError(f"expected Mapping, found {type(outputs)}")
+    if not isinstance(outputs, Mapping):
+        return
 
     messages = outputs.get("messages")
     if not messages:
diff --git a/tests/observability/core/test_agent365_exporter.py b/tests/observability/core/test_agent365_exporter.py
index 26bfe73e..8cc6fc91 100644
--- a/tests/observability/core/test_agent365_exporter.py
+++ b/tests/observability/core/test_agent365_exporter.py
@@ -322,9 +322,7 @@ def test_export_logging(self, mock_logger):
                     "(tenant: test-tenant-123, agent: test-agent-456)"
                 ),
                 # Should log token resolution success at DEBUG
-                unittest.mock.call.debug(
-                    "Token resolved successfully for agent test-agent-456"
-                ),
+                unittest.mock.call.debug("Token resolved successfully for agent test-agent-456"),
                 # Should log HTTP success at DEBUG
                 unittest.mock.call.debug(
                     "HTTP 200 success on attempt 1. "

From 84be10fd8dbc92c212e54942262f48b0610becd5 Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Mon, 16 Mar 2026 18:39:32 +0000
Subject: [PATCH 08/10] Move _parse_retry_after to exporters/utils.py as
 standalone parse_retry_after function

Co-authored-by: nikhilNava <211831449+nikhilNava@users.noreply.github.com>
---
 .../core/exporters/agent365_exporter.py       | 18 ++-----------
 .../observability/core/exporters/utils.py     | 27 +++++++++++++++++++
 2 files changed, 29 insertions(+), 16 deletions(-)

diff --git a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
index 117fd94d..8e6f6dd6 100644
--- a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
+++ b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
@@ -23,6 +23,7 @@
     hex_span_id,
     hex_trace_id,
     kind_name,
+    parse_retry_after,
     partition_by_identity,
     status_name,
     truncate_span,
@@ -162,21 +163,6 @@ def _truncate_text(text: str, max_length: int) -> str:
             return text[:max_length] + "..."
         return text
 
-    @staticmethod
-    def _parse_retry_after(resp: requests.Response) -> float | None:
-        """Parse the Retry-After header from a response.
-
-        Returns:
-            The number of seconds to wait, or None if the header is absent or invalid.
-        """
-        retry_after = resp.headers.get("Retry-After")
-        if retry_after is None:
-            return None
-        try:
-            return float(retry_after)
-        except (ValueError, TypeError):
-            return None
-
     def _post_with_retries(self, url: str, body: str, headers: dict[str, str]) -> bool:
         for attempt in range(DEFAULT_MAX_RETRIES + 1):
             try:
@@ -209,7 +195,7 @@ def _post_with_retries(self, url: str, body: str, headers: dict[str, str]) -> bo
                 # Retry transient
                 if resp.status_code in (408, 429) or 500 <= resp.status_code < 600:
                     # Respect Retry-After header for 429 responses
-                    retry_after = self._parse_retry_after(resp)
+                    retry_after = parse_retry_after(resp.headers)
                     if attempt < DEFAULT_MAX_RETRIES:
                         if retry_after is not None:
                             time.sleep(min(retry_after, 60.0))
diff --git a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/utils.py b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/utils.py
index eef34a00..d48bd1ab 100644
--- a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/utils.py
+++ b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/utils.py
@@ -1,6 +1,8 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT License.
 
+from __future__ import annotations
+
 import json
 import logging
 import os
@@ -230,6 +232,31 @@ def build_export_url(
     return f"https://{endpoint}{endpoint_path}?api-version=1"
 
 
+def parse_retry_after(headers: dict[str, str]) -> float | None:
+    """Parse the ``Retry-After`` header value.
+
+    Only numeric (seconds) values are supported.  HTTP-date values
+    (e.g. ``Wed, 21 Oct 2025 07:28:00 GMT``) are intentionally ignored
+    and treated as absent, falling back to exponential backoff.
+
+    Args:
+        headers: Response headers mapping.
+
+    Returns:
+        The number of seconds to wait, or ``None`` if the header is
+        absent, non-numeric, or otherwise invalid.
+    """
+    retry_after = headers.get("Retry-After")
+    if retry_after is None:
+        return None
+    try:
+        return float(retry_after)
+    except (ValueError, TypeError):
+        # Intentionally ignore HTTP-date formatted Retry-After values;
+        # callers should fall back to exponential backoff.
+        return None
+
+
 def is_agent365_exporter_enabled() -> bool:
     """Check if Agent 365 exporter is enabled."""
     # Check environment variable

From c08b24f54e9463203236aa2dac3dff43aa5663ad Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Tue, 17 Mar 2026 16:19:07 +0000
Subject: [PATCH 09/10] Replace type(e).__name__ with str(e) in exporter error
 logging per PR review

Co-authored-by: nikhilNava <211831449+nikhilNava@users.noreply.github.com>
---
 .../observability/core/exporters/agent365_exporter.py      | 7 ++-----
 1 file changed, 2 insertions(+), 5 deletions(-)

diff --git a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
index 8e6f6dd6..5920dec3 100644
--- a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
+++ b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/exporters/agent365_exporter.py
@@ -122,8 +122,7 @@ def export(self, spans: Sequence[ReadableSpan]) -> SpanExportResult:
                 except Exception as e:
                     # If token resolution fails, treat as failure for this group
                     logger.error(
-                        f"Token resolution failed for agent {agent_id}, "
-                        f"tenant {tenant_id}: {type(e).__name__}"
+                        f"Token resolution failed for agent {agent_id}, tenant {tenant_id}: {e}"
                     )
                     any_failure = True
                     continue
@@ -225,9 +224,7 @@ def _post_with_retries(self, url: str, body: str, headers: dict[str, str]) -> bo
                     time.sleep(0.5 * (2**attempt))
                     continue
                 # Final attempt failed
-                logger.error(
-                    f"Request failed after {DEFAULT_MAX_RETRIES + 1} attempts: {type(e).__name__}"
-                )
+                logger.error(f"Request failed after {DEFAULT_MAX_RETRIES + 1} attempts: {e}")
                 return False
         return False
 

From f02e68c496b33ffec25ed11334ee33d9006f0b02 Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Tue, 17 Mar 2026 19:13:58 +0000
Subject: [PATCH 10/10] feat: add bounded collections for LangChain tracer and
 OutputScope

- Convert LangChain _spans_by_run from unbounded DictWithLock to
  bounded OrderedDict with _MAX_TRACKED_RUNS=10000 cap
- Add _cap_ordered_dict helper for FIFO eviction (matching OpenAI pattern)
- Add thread-safe lock usage for _spans_by_run in error handlers
- Add _MAX_OUTPUT_MESSAGES=5000 cap for OutputScope._output_messages
- Add unit tests for both bounded collections

Co-authored-by: nikhilNava <211831449+nikhilNava@users.noreply.github.com>
---
 .../core/spans_scopes/output_scope.py         |   5 +
 .../extensions/langchain/tracer.py            |  34 ++++--
 .../core/test_output_scope_bounded.py         | 100 ++++++++++++++++
 .../langchain/test_tracer_bounded.py          | 109 ++++++++++++++++++
 4 files changed, 241 insertions(+), 7 deletions(-)
 create mode 100644 tests/observability/core/test_output_scope_bounded.py
 create mode 100644 tests/observability/extensions/langchain/test_tracer_bounded.py

diff --git a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/spans_scopes/output_scope.py b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/spans_scopes/output_scope.py
index 873a9dc9..8f128adf 100644
--- a/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/spans_scopes/output_scope.py
+++ b/libraries/microsoft-agents-a365-observability-core/microsoft_agents_a365/observability/core/spans_scopes/output_scope.py
@@ -16,6 +16,8 @@
 class OutputScope(OpenTelemetryScope):
     """Provides OpenTelemetry tracing scope for output messages."""
 
+    _MAX_OUTPUT_MESSAGES = 5000
+
     @staticmethod
     def start(
         agent_details: AgentDetails,
@@ -82,9 +84,12 @@ def record_output_messages(self, messages: list[str]) -> None:
         """Records the output messages for telemetry tracking.
 
         Appends the provided messages to the accumulated output messages list.
+        The list is capped at _MAX_OUTPUT_MESSAGES to prevent unbounded memory growth.
 
         Args:
             messages: List of output messages to append
         """
         self._output_messages.extend(messages)
+        if len(self._output_messages) > self._MAX_OUTPUT_MESSAGES:
+            self._output_messages = self._output_messages[-self._MAX_OUTPUT_MESSAGES :]
         self.set_tag_maybe(GEN_AI_OUTPUT_MESSAGES_KEY, safe_json_dumps(self._output_messages))
diff --git a/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/tracer.py b/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/tracer.py
index 3204912b..b5cb3dcd 100644
--- a/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/tracer.py
+++ b/libraries/microsoft-agents-a365-observability-extensions-langchain/microsoft_agents_a365/observability/extensions/langchain/tracer.py
@@ -3,6 +3,7 @@
 
 import logging
 import re
+from collections import OrderedDict
 from collections.abc import Iterator
 from itertools import chain
 from threading import RLock
@@ -69,6 +70,8 @@
 
 
 class CustomLangChainTracer(BaseTracer):
+    _MAX_TRACKED_RUNS = 10000
+
     __slots__ = (
         "_tracer",
         "_separate_trace_from_runtime_context",
@@ -98,11 +101,18 @@ def __init__(
         self.run_map = DictWithLock[str, Run](self.run_map)
         self._tracer = tracer
         self._separate_trace_from_runtime_context = separate_trace_from_runtime_context
-        self._spans_by_run: dict[UUID, Span] = DictWithLock[UUID, Span]()
+        self._spans_by_run: OrderedDict[UUID, Span] = OrderedDict()
         self._lock = RLock()  # handlers may be run in a thread by langchain
 
     def get_span(self, run_id: UUID) -> Span | None:
-        return self._spans_by_run.get(run_id)
+        with self._lock:
+            return self._spans_by_run.get(run_id)
+
+    @staticmethod
+    def _cap_ordered_dict(d: OrderedDict, max_size: int) -> None:
+        """Evict oldest entries from an OrderedDict to stay within max_size."""
+        while len(d) > max_size:
+            d.popitem(last=False)
 
     def _start_trace(self, run: Run) -> None:
         self.run_map[str(run.id)] = run
@@ -142,12 +152,14 @@ def _start_trace(self, run: Run) -> None:
         # token = context_api.attach(context)
         with self._lock:
             self._spans_by_run[run.id] = span
+            self._cap_ordered_dict(self._spans_by_run, self._MAX_TRACKED_RUNS)
 
     def _end_trace(self, run: Run) -> None:
         self.run_map.pop(str(run.id), None)
         if context_api.get_value(_SUPPRESS_INSTRUMENTATION_KEY):
             return
-        span = self._spans_by_run.pop(run.id, None)
+        with self._lock:
+            span = self._spans_by_run.pop(run.id, None)
         if span:
             try:
                 _update_span(span, run)
@@ -162,24 +174,32 @@ def _persist_run(self, run: Run) -> None:
         pass
 
     def on_llm_error(self, error: BaseException, *args: Any, run_id: UUID, **kwargs: Any) -> Run:
-        if span := self._spans_by_run.get(run_id):
+        with self._lock:
+            span = self._spans_by_run.get(run_id)
+        if span:
             record_exception(span, error)
         return super().on_llm_error(error, *args, run_id=run_id, **kwargs)
 
     def on_chain_error(self, error: BaseException, *args: Any, run_id: UUID, **kwargs: Any) -> Run:
-        if span := self._spans_by_run.get(run_id):
+        with self._lock:
+            span = self._spans_by_run.get(run_id)
+        if span:
             record_exception(span, error)
         return super().on_chain_error(error, *args, run_id=run_id, **kwargs)
 
     def on_retriever_error(
         self, error: BaseException, *args: Any, run_id: UUID, **kwargs: Any
     ) -> Run:
-        if span := self._spans_by_run.get(run_id):
+        with self._lock:
+            span = self._spans_by_run.get(run_id)
+        if span:
             record_exception(span, error)
         return super().on_retriever_error(error, *args, run_id=run_id, **kwargs)
 
     def on_tool_error(self, error: BaseException, *args: Any, run_id: UUID, **kwargs: Any) -> Run:
-        if span := self._spans_by_run.get(run_id):
+        with self._lock:
+            span = self._spans_by_run.get(run_id)
+        if span:
             record_exception(span, error)
         return super().on_tool_error(error, *args, run_id=run_id, **kwargs)
 
diff --git a/tests/observability/core/test_output_scope_bounded.py b/tests/observability/core/test_output_scope_bounded.py
new file mode 100644
index 00000000..deaa4fae
--- /dev/null
+++ b/tests/observability/core/test_output_scope_bounded.py
@@ -0,0 +1,100 @@
+# Copyright (c) Microsoft Corporation.
+# Licensed under the MIT License.
+
+"""Tests for bounded output messages in OutputScope."""
+
+import unittest
+from unittest.mock import MagicMock, patch
+
+from microsoft_agents_a365.observability.core.spans_scopes.output_scope import OutputScope
+
+
+class TestOutputScopeBounded(unittest.TestCase):
+    """Tests that OutputScope._output_messages list is properly bounded."""
+
+    def _make_scope(self, initial_messages: list[str] | None = None) -> OutputScope:
+        """Create an OutputScope with mocked dependencies."""
+        agent_details = MagicMock()
+        agent_details.agent_id = "test-agent"
+        agent_details.agent_name = "Test Agent"
+        agent_details.agent_description = None
+        agent_details.platform_id = None
+        agent_details.conversation_id = None
+        agent_details.icon_uri = None
+        agent_details.agent_auid = None
+        agent_details.agent_upn = None
+        agent_details.agent_blueprint_id = None
+
+        tenant_details = MagicMock()
+        tenant_details.tenant_id = "test-tenant"
+
+        response = MagicMock()
+        response.messages = initial_messages or ["hello"]
+
+        with patch.object(OutputScope, "__init__", lambda self, *a, **kw: None):
+            scope = OutputScope.__new__(OutputScope)
+            scope._output_messages = list(response.messages)
+            scope.set_tag_maybe = MagicMock()
+
+        return scope
+
+    def test_max_output_messages_default(self):
+        """Default _MAX_OUTPUT_MESSAGES should be 5000."""
+        self.assertEqual(OutputScope._MAX_OUTPUT_MESSAGES, 5000)
+
+    def test_record_output_messages_within_limit(self):
+        """Messages under the limit should not be truncated."""
+        scope = self._make_scope(["initial"])
+        scope.record_output_messages(["msg1", "msg2", "msg3"])
+        self.assertEqual(len(scope._output_messages), 4)
+        self.assertEqual(scope._output_messages, ["initial", "msg1", "msg2", "msg3"])
+
+    def test_record_output_messages_exceeds_limit(self):
+        """Messages exceeding the limit should be truncated to keep newest."""
+        scope = self._make_scope([])
+        original_max = OutputScope._MAX_OUTPUT_MESSAGES
+        try:
+            OutputScope._MAX_OUTPUT_MESSAGES = 10
+
+            # Add 15 messages
+            scope.record_output_messages([f"msg_{i}" for i in range(15)])
+
+            # Should be capped at 10 (keeping the newest)
+            self.assertEqual(len(scope._output_messages), 10)
+            # Oldest 5 should be gone, newest 10 should remain
+            self.assertEqual(scope._output_messages[0], "msg_5")
+            self.assertEqual(scope._output_messages[-1], "msg_14")
+        finally:
+            OutputScope._MAX_OUTPUT_MESSAGES = original_max
+
+    def test_record_output_messages_multiple_calls_capped(self):
+        """Multiple calls to record_output_messages should stay bounded."""
+        scope = self._make_scope([])
+        original_max = OutputScope._MAX_OUTPUT_MESSAGES
+        try:
+            OutputScope._MAX_OUTPUT_MESSAGES = 5
+
+            for batch in range(4):
+                scope.record_output_messages([f"batch{batch}_msg{i}" for i in range(3)])
+
+            # Total of 12 messages added in 4 batches, should be capped at 5
+            self.assertLessEqual(len(scope._output_messages), 5)
+            # Latest messages should be from the last batches
+            self.assertIn("batch3_msg2", scope._output_messages)
+        finally:
+            OutputScope._MAX_OUTPUT_MESSAGES = original_max
+
+    def test_record_output_messages_exactly_at_limit(self):
+        """Messages exactly at the limit should not be truncated."""
+        scope = self._make_scope([])
+        original_max = OutputScope._MAX_OUTPUT_MESSAGES
+        try:
+            OutputScope._MAX_OUTPUT_MESSAGES = 5
+            scope.record_output_messages([f"msg_{i}" for i in range(5)])
+            self.assertEqual(len(scope._output_messages), 5)
+        finally:
+            OutputScope._MAX_OUTPUT_MESSAGES = original_max
+
+
+if __name__ == "__main__":
+    unittest.main()
diff --git a/tests/observability/extensions/langchain/test_tracer_bounded.py b/tests/observability/extensions/langchain/test_tracer_bounded.py
new file mode 100644
index 00000000..b70c920b
--- /dev/null
+++ b/tests/observability/extensions/langchain/test_tracer_bounded.py
@@ -0,0 +1,109 @@
+# Copyright (c) Microsoft Corporation.
+# Licensed under the MIT License.
+
+"""Tests for bounded collections in the LangChain tracer."""
+
+import unittest
+from collections import OrderedDict
+from unittest.mock import MagicMock, patch
+from uuid import uuid4
+
+from microsoft_agents_a365.observability.extensions.langchain.tracer import (
+    CustomLangChainTracer,
+)
+
+
+class TestLangChainTracerBounded(unittest.TestCase):
+    """Tests that LangChain tracer collections are properly bounded."""
+
+    def _make_tracer(self) -> CustomLangChainTracer:
+        """Create a tracer with a mock OTel tracer."""
+        mock_otel_tracer = MagicMock()
+        mock_span = MagicMock()
+        mock_otel_tracer.start_span.return_value = mock_span
+        return CustomLangChainTracer(
+            tracer=mock_otel_tracer,
+            separate_trace_from_runtime_context=True,
+        )
+
+    def test_spans_by_run_is_ordered_dict(self):
+        """_spans_by_run should be an OrderedDict for bounded eviction."""
+        tracer = self._make_tracer()
+        self.assertIsInstance(tracer._spans_by_run, OrderedDict)
+
+    def test_cap_ordered_dict_evicts_oldest(self):
+        """_cap_ordered_dict should evict oldest entries (FIFO)."""
+        d: OrderedDict[str, int] = OrderedDict()
+        for i in range(15):
+            d[f"key_{i}"] = i
+        CustomLangChainTracer._cap_ordered_dict(d, 10)
+
+        self.assertEqual(len(d), 10)
+        # oldest 5 should be gone
+        for i in range(5):
+            self.assertNotIn(f"key_{i}", d)
+        # newest 10 should remain
+        for i in range(5, 15):
+            self.assertIn(f"key_{i}", d)
+            self.assertEqual(d[f"key_{i}"], i)
+
+    def test_cap_ordered_dict_noop_when_under_limit(self):
+        """_cap_ordered_dict should be a no-op when size is under limit."""
+        d: OrderedDict[str, int] = OrderedDict()
+        for i in range(5):
+            d[f"key_{i}"] = i
+        CustomLangChainTracer._cap_ordered_dict(d, 10)
+        self.assertEqual(len(d), 5)
+
+    def test_spans_by_run_bounded_on_start_trace(self):
+        """_spans_by_run should be bounded when _start_trace adds entries."""
+        tracer = self._make_tracer()
+        # Use a small cap for testing
+        original_max = CustomLangChainTracer._MAX_TRACKED_RUNS
+        try:
+            CustomLangChainTracer._MAX_TRACKED_RUNS = 5
+
+            # Add more runs than the cap
+            for i in range(10):
+                run = MagicMock()
+                run.id = uuid4()
+                run.parent_run_id = None
+                run.run_type = "llm"
+                run.name = f"test_run_{i}"
+                run.start_time = MagicMock()
+
+                with patch(
+                    "microsoft_agents_a365.observability.extensions.langchain.tracer"
+                    ".context_api.get_value",
+                    return_value=None,
+                ):
+                    tracer._start_trace(run)
+
+            # Should be capped at 5
+            self.assertLessEqual(len(tracer._spans_by_run), 5)
+        finally:
+            CustomLangChainTracer._MAX_TRACKED_RUNS = original_max
+
+    def test_get_span_returns_none_for_missing(self):
+        """get_span should return None for non-existent run_id."""
+        tracer = self._make_tracer()
+        result = tracer.get_span(uuid4())
+        self.assertIsNone(result)
+
+    def test_get_span_returns_span_for_existing(self):
+        """get_span should return the span for existing run_id."""
+        tracer = self._make_tracer()
+        run_id = uuid4()
+        mock_span = MagicMock()
+        with tracer._lock:
+            tracer._spans_by_run[run_id] = mock_span
+        result = tracer.get_span(run_id)
+        self.assertEqual(result, mock_span)
+
+    def test_max_tracked_runs_default(self):
+        """Default _MAX_TRACKED_RUNS should be 10000."""
+        self.assertEqual(CustomLangChainTracer._MAX_TRACKED_RUNS, 10000)
+
+
+if __name__ == "__main__":
+    unittest.main()