fix(ai): truncate long message histories #4885

shellmayr · 2025-10-03T12:42:03Z

Add truncation for long message histories to prevent spans from being rejected due to exceeding size limits
Messages are removed, oldest first, if the span attribute exceeds 20kB, and a _meta entry is added when removed
Huggingface Hub currently doesn't seem to send spans that are OTEL compatible - the attribute is current just a string as evidenced by this test
Annotations
- Removing entire messages will cause a _meta tag to be set via AnnotatedValue

Truncation for single messages that exceed the limit will be added separately

Closes TET-1208

linear · 2025-10-03T12:43:28Z

TET-1208 Python SDK: truncate gen_ai messages

codecov · 2025-10-15T09:11:51Z

❌ 4 Tests Failed:

Tests completed	Failed	Passed	Skipped
23770	4	23766	1716

View the top 3 failed test(s) by shortest run time

tests.integrations.openai_agents.test_openai_agents::test_tool_execution_span

Stack Traces | 0.258s run time

.../integrations/openai_agents/test_openai_agents.py:432: in test_tool_execution_span
    await agents.Runner.run(
.tox/py3.11-openai_agents-v0.0.19/lib/python3.11............/site-packages/agents/run.py:199: in run
    return await runner.run(
.../openai_agents/patches/runner.py:43: in wrapper
    raise exc from None
.../openai_agents/patches/runner.py:33: in wrapper
    result = await original_func(*args, **kwargs)
             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
.tox/py3.11-openai_agents-v0.0.19/lib/python3.11............/site-packages/agents/run.py:417: in run
    turn_result = await self._run_single_turn(
.../openai_agents/patches/agent_run.py:78: in patched_run_single_turn
    result = await original_run_single_turn(*args, **kwargs)
             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
.tox/py3.11-openai_agents-v0.0.19/lib/python3.11............/site-packages/agents/run.py:905: in _run_single_turn
    new_response = await cls._get_new_response(
.tox/py3.11-openai_agents-v0.0.19/lib/python3.11............/site-packages/agents/run.py:1066: in _get_new_response
    new_response = await model.get_response(
.../openai_agents/patches/models.py:42: in wrapped_get_response
    update_ai_client_span(span, agent, kwargs, result)
.../openai_agents/spans/ai_client.py:40: in update_ai_client_span
    _set_input_data(span, get_response_kwargs)
.../integrations/openai_agents/utils.py:141: in _set_input_data
    messages_data = truncate_and_annotate_messages(
sentry_sdk/ai/utils.py:171: in truncate_and_annotate_messages
    truncated_messages = truncate_messages_by_size(messages, max_bytes)
                         ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
sentry_sdk/ai/utils.py:118: in truncate_messages_by_size
    serialized_json = json.dumps(truncated_messages, separators=(",", ":"))
                      ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
.../hostedtoolcache/Python/3.11.13............/x64/lib/python3.11/json/__init__.py:238: in dumps
    **kw).encode(obj)
          ^^^^^^^^^^^
.../hostedtoolcache/Python/3.11.13............/x64/lib/python3.11/json/encoder.py:200: in encode
    chunks = self.iterencode(o, _one_shot=True)
             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
.../hostedtoolcache/Python/3.11.13............/x64/lib/python3.11/json/encoder.py:258: in iterencode
    return _iterencode(o, 0)
           ^^^^^^^^^^^^^^^^^
.../hostedtoolcache/Python/3.11.13............/x64/lib/python3.11/json/encoder.py:180: in default
    raise TypeError(f'Object of type {o.__class__.__name__} '
E   TypeError: Object of type SerializationIterator is not JSON serializable

tests.integrations.openai_agents.test_openai_agents::test_tool_execution_span

Stack Traces | 0.412s run time

.../integrations/openai_agents/test_openai_agents.py:432: in test_tool_execution_span
    await agents.Runner.run(
.tox/py3.10-openai_agents-v0.0.19/lib/python3.10............/site-packages/agents/run.py:199: in run
    return await runner.run(
.../openai_agents/patches/runner.py:43: in wrapper
    raise exc from None
.../openai_agents/patches/runner.py:33: in wrapper
    result = await original_func(*args, **kwargs)
.tox/py3.10-openai_agents-v0.0.19/lib/python3.10............/site-packages/agents/run.py:417: in run
    turn_result = await self._run_single_turn(
.../openai_agents/patches/agent_run.py:78: in patched_run_single_turn
    result = await original_run_single_turn(*args, **kwargs)
.tox/py3.10-openai_agents-v0.0.19/lib/python3.10............/site-packages/agents/run.py:905: in _run_single_turn
    new_response = await cls._get_new_response(
.tox/py3.10-openai_agents-v0.0.19/lib/python3.10............/site-packages/agents/run.py:1066: in _get_new_response
    new_response = await model.get_response(
.../openai_agents/patches/models.py:42: in wrapped_get_response
    update_ai_client_span(span, agent, kwargs, result)
.../openai_agents/spans/ai_client.py:40: in update_ai_client_span
    _set_input_data(span, get_response_kwargs)
.../integrations/openai_agents/utils.py:141: in _set_input_data
    messages_data = truncate_and_annotate_messages(
sentry_sdk/ai/utils.py:171: in truncate_and_annotate_messages
    truncated_messages = truncate_messages_by_size(messages, max_bytes)
sentry_sdk/ai/utils.py:118: in truncate_messages_by_size
    serialized_json = json.dumps(truncated_messages, separators=(",", ":"))
.../hostedtoolcache/Python/3.10.18............/x64/lib/python3.10/json/__init__.py:238: in dumps
    **kw).encode(obj)
.../hostedtoolcache/Python/3.10.18............/x64/lib/python3.10/json/encoder.py:199: in encode
    chunks = self.iterencode(o, _one_shot=True)
.../hostedtoolcache/Python/3.10.18............/x64/lib/python3.10/json/encoder.py:257: in iterencode
    return _iterencode(o, 0)
.../hostedtoolcache/Python/3.10.18............/x64/lib/python3.10/json/encoder.py:179: in default
    raise TypeError(f'Object of type {o.__class__.__name__} '
E   TypeError: Object of type SerializationIterator is not JSON serializable

tests.integrations.openai_agents.test_openai_agents::test_tool_execution_span

Stack Traces | 0.486s run time

.../integrations/openai_agents/test_openai_agents.py:432: in test_tool_execution_span
    await agents.Runner.run(
.tox/py3.12-openai_agents-v0.2.11/lib/python3.12............/site-packages/agents/run.py:267: in run
    return await runner.run(
.../openai_agents/patches/runner.py:43: in wrapper
    raise exc from None
.../openai_agents/patches/runner.py:33: in wrapper
    result = await original_func(*args, **kwargs)
             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
.tox/py3.12-openai_agents-v0.2.11/lib/python3.12............/site-packages/agents/run.py:504: in run
    turn_result = await self._run_single_turn(
.../openai_agents/patches/agent_run.py:78: in patched_run_single_turn
    result = await original_run_single_turn(*args, **kwargs)
             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
.tox/py3.12-openai_agents-v0.2.11/lib/python3.12............/site-packages/agents/run.py:1159: in _run_single_turn
    new_response = await cls._get_new_response(
.tox/py3.12-openai_agents-v0.2.11/lib/python3.12............/site-packages/agents/run.py:1398: in _get_new_response
    new_response = await model.get_response(
.../openai_agents/patches/models.py:42: in wrapped_get_response
    update_ai_client_span(span, agent, kwargs, result)
.../openai_agents/spans/ai_client.py:40: in update_ai_client_span
    _set_input_data(span, get_response_kwargs)
.../integrations/openai_agents/utils.py:141: in _set_input_data
    messages_data = truncate_and_annotate_messages(
sentry_sdk/ai/utils.py:171: in truncate_and_annotate_messages
    truncated_messages = truncate_messages_by_size(messages, max_bytes)
                         ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
sentry_sdk/ai/utils.py:118: in truncate_messages_by_size
    serialized_json = json.dumps(truncated_messages, separators=(",", ":"))
                      ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
.../hostedtoolcache/Python/3.12.11............/x64/lib/python3.12/json/__init__.py:238: in dumps
    **kw).encode(obj)
          ^^^^^^^^^^^
.../hostedtoolcache/Python/3.12.11............/x64/lib/python3.12/json/encoder.py:200: in encode
    chunks = self.iterencode(o, _one_shot=True)
             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
.../hostedtoolcache/Python/3.12.11............/x64/lib/python3.12/json/encoder.py:258: in iterencode
    return _iterencode(o, 0)
           ^^^^^^^^^^^^^^^^^
.../hostedtoolcache/Python/3.12.11............/x64/lib/python3.12/json/encoder.py:180: in default
    raise TypeError(f'Object of type {o.__class__.__name__} '
E   TypeError: Object of type SerializationIterator is not JSON serializable

tests.integrations.openai_agents.test_openai_agents::test_tool_execution_span

Stack Traces | 0.501s run time

.../integrations/openai_agents/test_openai_agents.py:432: in test_tool_execution_span
    await agents.Runner.run(
.tox/py3.13-openai_agents-v0.2.11/lib/python3.13............/site-packages/agents/run.py:267: in run
    return await runner.run(
.../openai_agents/patches/runner.py:43: in wrapper
    raise exc from None
.../openai_agents/patches/runner.py:33: in wrapper
    result = await original_func(*args, **kwargs)
             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
.tox/py3.13-openai_agents-v0.2.11/lib/python3.13............/site-packages/agents/run.py:504: in run
    turn_result = await self._run_single_turn(
.../openai_agents/patches/agent_run.py:78: in patched_run_single_turn
    result = await original_run_single_turn(*args, **kwargs)
             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
.tox/py3.13-openai_agents-v0.2.11/lib/python3.13............/site-packages/agents/run.py:1159: in _run_single_turn
    new_response = await cls._get_new_response(
.tox/py3.13-openai_agents-v0.2.11/lib/python3.13............/site-packages/agents/run.py:1398: in _get_new_response
    new_response = await model.get_response(
.../openai_agents/patches/models.py:42: in wrapped_get_response
    update_ai_client_span(span, agent, kwargs, result)
.../openai_agents/spans/ai_client.py:40: in update_ai_client_span
    _set_input_data(span, get_response_kwargs)
.../integrations/openai_agents/utils.py:141: in _set_input_data
    messages_data = truncate_and_annotate_messages(
sentry_sdk/ai/utils.py:171: in truncate_and_annotate_messages
    truncated_messages = truncate_messages_by_size(messages, max_bytes)
                         ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
sentry_sdk/ai/utils.py:118: in truncate_messages_by_size
    serialized_json = json.dumps(truncated_messages, separators=(",", ":"))
                      ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
.../hostedtoolcache/Python/3.13.7............/x64/lib/python3.13/json/__init__.py:238: in dumps
    **kw).encode(obj)
          ^^^^^^^^^^^
.../hostedtoolcache/Python/3.13.7............/x64/lib/python3.13/json/encoder.py:200: in encode
    chunks = self.iterencode(o, _one_shot=True)
             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
.../hostedtoolcache/Python/3.13.7............/x64/lib/python3.13/json/encoder.py:261: in iterencode
    return _iterencode(o, 0)
           ^^^^^^^^^^^^^^^^^
.../hostedtoolcache/Python/3.13.7............/x64/lib/python3.13/json/encoder.py:180: in default
    raise TypeError(f'Object of type {o.__class__.__name__} '
E   TypeError: Object of type SerializationIterator is not JSON serializable

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shellmayr · 2025-11-07T08:39:16Z

These were done individually - closing.

shellmayr force-pushed the shellmayr/fix/truncate-long-gen_ai-messages branch from 92329fb to f66a772 Compare October 7, 2025 14:20

shellmayr added 8 commits October 9, 2025 10:40

fix(ai): truncate long message histories

40f1ecb

wip

bf386cd

integrate message truncation in langchain & langgraph

d4bfa31

update limit

e95be82

add meta entries

a137be5

truncate message lengths without meta so far

e54151c

truncate simply

5b378fd

remove very small limit tests -- not applicable constraint

294c66c

shellmayr force-pushed the shellmayr/fix/truncate-long-gen_ai-messages branch from c6716c6 to 294c66c Compare October 9, 2025 09:14

shellmayr added 8 commits October 9, 2025 12:47

move message utils to utils, add to all integrations

630a472

clean up tests

6dcc344

fix test

e105108

fix test

8046c1b

dont truncate in huggingface hub

cb2e803

fix litellm test

455136a

use annotatedvalue instead of previous approach

8f0e049

fix tests for messages as list

ad4f10a

shellmayr added 7 commits October 15, 2025 11:19

fix some more tests

6ac119b

fix test

da8813b

wip

44ec306

remove single message size truncation for now

ed2f642

wip

cf6f70b

fix test

6e173b4

fix test

a220aa9

shellmayr mentioned this pull request Oct 16, 2025

fix(ai): introduce message truncation for openai #4946

Merged

shellmayr closed this Nov 7, 2025

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