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Evaluate conversations in the cloud (preview)

Assess complete conversations from datasets or Application Insights traces at the turn or conversation level.

Prerequisites

  • Complete the cloud evaluation prerequisites and client setup.
  • Conversation data with a messages array, or traced production conversations in Application Insights.
  • Conversation-level evaluators that support the selected evaluation level.

The examples use the SDK client configured in Set up the SDK client.

Evaluate conversation datasets

Evaluate complete conversations to assess agent quality across entire user interactions - not just individual responses. Use conversation-level evaluation to identify quality problems like incomplete task resolution, user frustration, and tool-call regressions that turn-level evaluation misses.

For example, consider a support agent where the user grows frustrated over multiple turns:

Turn 1 — User: "I need to reset my password." Agent: "I found your account. I'll send a reset link."

Turn 2 — User: "I didn't get the email." Agent: "I've resent the link. Please check spam."

Turn 3 — User: "Still nothing. Can you just reset it directly?" Agent: "I've sent another reset link."

A turn-level evaluator scores only the last response - which is polite and takes action - so it scores well. A conversation-level evaluator grading customer satisfaction across the conversation flags that the agent repeated the same failing action three times without trying an alternative, leaving the user's problem unresolved.

Conversation-level evaluation differs from turn-level evaluation in several ways:

Aspect Turn-level Conversation-level
Scope Individual query-response pairs Complete conversations with multiple exchanges
Metrics Per-response quality and safety Conversation-level outcomes and user satisfaction
Data format JSONL with query and response fields JSONL with messages array containing the full conversation
Use case Testing individual model responses Testing end-to-end agent experiences

Conversation-level evaluation supports four data source options:

Option When to use Data source type
From dataset or inline You have local conversation traces or test data jsonl with file_id or file_content
By conversation ID You want to evaluate specific conversations from App Insights azure_ai_trace_data_source_preview with trace_source
By agent filter with sampling You want to assess overall agent quality across sampled production traffic azure_ai_trace_data_source_preview with trace_source
Simulated conversations You want to generate synthetic test conversations azure_ai_target_completions with conversation_gen_preview

Choose an evaluation level

The evaluation_level parameter on the run determines whether evaluators score individual turns or complete conversations:

Value Behavior
"turn" Evaluators score each turn independently.
"conversation" Evaluators score the entire conversation as a whole.
(omitted) Defaults to "turn".

Important

Evaluator compatibility: Each evaluator supports specific evaluation levels. Check the evaluator's supported_evaluation_levels field in the evaluator catalog.

  • Turn-only evaluators (for example, fluency, relevance) can't be used with evaluation_level="conversation".
  • Currently, all conversation-level evaluators support both "turn" and "conversation" levels.

Common errors

Error Cause Solution
Incompatible evaluation level Using evaluation_level="conversation" with a turn-only evaluator Remove the turn-only evaluator or change to evaluation_level="turn"

Prepare conversation data

Create a JSONL file where each line contains a complete conversation in the messages field. Each message should include a role (user, assistant, or system) and content. For a complete example, see the conversation evaluation samples in the SDK.

 {"messages": [{"role": "user", "content": "What's my account balance?"}, {"role": "assistant", "content": "Your current balance is $1,234.56."}, {"role": "user", "content": "Thanks!"}, {"role": "assistant", "content": "You're welcome! Is there anything else?"}]}

You can also include tool definitions and tool calls if your agent uses tools:

{"messages": [{"role": "user", "content": "What is the capital/major city of France?"}, {"role": "assistant", "content": "Paris"}]}
{"messages": [{"role": "user", "content": "How do I reverse a string in Python?"}, {"role": "assistant", "content": "You can reverse a string in Python by using slicing: string[::-1]"}]}
{"messages": [{"role": "user", "content": "What are the main causes of climate change?"}, {"role": "assistant", "content": "The main causes of climate change are the increase in greenhouse gases in the atmosphere, primarily due to human activities such as burning fossil fuels and deforestation."}]}
{"messages": [{"role": "user", "content": "What's my account balance?"}, {"role": "assistant", "content": null, "tool_calls": [{"id": "call_abc123", "type": "function", "function": {"name": "get_account_balance", "arguments": "{\"account_id\": \"ACCT-7890\"}"}}]}, {"role": "tool", "tool_call_id": "call_abc123", "content": "{ \"balance\": 1234.56, \"currency\": \"USD\" }"}, {"role": "assistant", "content": "Your current balance is 1,234.56."}, {"role": "user", "content": "Thanks!"}, {"role": "assistant", "content": "You're welcome! Is there anything else?"}], "tool_definitions": [{"name": "get_account_balance", "description": "Retrieves the current balance for a customer account", "parameters": {"type": "object", "properties": {"account_id": {"type": "string"}}, "required": ["account_id"]}}]}
{"messages": [{"role": "user", "content": "Explain the theory of relativity in simple terms."}, {"role": "assistant", "content": "Einstein's theory of relativity shows that space and time are interconnected and relative to the observer's frame of reference."}]}
{"messages": [{"role": "user", "content": "What's the weather in Seattle?"}, {"role": "assistant", "content": null, "tool_calls": [{"id": "call_002", "type": "function", "function": {"name": "get_weather", "arguments": "{\"location\": \"Seattle, WA\"}"}}]}, {"role": "tool", "tool_call_id": "call_002", "content": "{ \"temperature\": 55, \"condition\": \"Cloudy\" }"}, {"role": "assistant", "content": "It's currently 55F and cloudy in Seattle."}], "tool_definitions": [{"name": "get_weather", "description": "Get the current weather for a location", "parameters": {"type": "object", "properties": {"location": {"type": "string"}}, "required": ["location"]}}]}
{"messages": [{"role": "user", "content": "What is the tallest mountain in the world?"}, {"role": "assistant", "content": "Mount Everest is the tallest mountain in the world."}]}
{"messages": [{"role": "user", "content": "Is 4 x 2 = 16?"}, {"role": "assistant", "content": "No, 4 x 2 = 8."}]}
{"messages": [{"role": "user", "content": "What is the best Italian desert?"}, {"role": "assistant", "content": "Tiramisu is a popular Italian dessert."}]}
{"messages": [{"role": "user", "content": "What is the chemical formula for water?"}, {"role": "assistant", "content": "The chemical formula for water is H2O."}]}

Define the data schema and evaluators

Specify the schema for your conversation data, "messages", and select evaluators designed for conversation-level evaluation. Conversation-level evaluators assess the entire interaction rather than individual turns.

pip install "azure-ai-projects>=2.2.0"
import os
from openai.types.eval_create_params import DataSourceConfigCustom
from azure.identity import DefaultAzureCredential
from azure.ai.projects import AIProjectClient
from azure.ai.projects.models import TestingCriterionAzureAIEvaluator

endpoint = os.environ["FOUNDRY_PROJECT_ENDPOINT"]
model_deployment_name = os.environ["FOUNDRY_MODEL_NAME"]

with (
    DefaultAzureCredential() as credential,
    AIProjectClient(endpoint=endpoint, credential=credential) as project_client,
    project_client.get_openai_client() as openai_client,
):
    data_source_config = DataSourceConfigCustom(
        type="custom",
        item_schema={
            "type": "object",
            "properties": {
                "messages": {"type": "array"},
                "tool_definitions": {"type": "array"},
            },
            "required": ["messages"],
        },
        include_sample_schema=False,
    )

    testing_criteria = [
        TestingCriterionAzureAIEvaluator(
            type="azure_ai_evaluator",
            name="customer_satisfaction",
            evaluator_name="builtin.customer_satisfaction",
            initialization_parameters={"model": model_deployment_name},
            data_mapping={"messages": "{{item.messages}}"},
        ),
        TestingCriterionAzureAIEvaluator(
            type="azure_ai_evaluator",
            name="task_completion",
            evaluator_name="builtin.task_completion",
            initialization_parameters={"model": model_deployment_name},
            data_mapping={"messages": "{{item.messages}}"},
        ),
        TestingCriterionAzureAIEvaluator(
            type="azure_ai_evaluator",
            name="conversation_coherence",
            evaluator_name="builtin.coherence",
            initialization_parameters={"model": model_deployment_name},
            data_mapping={"messages": "{{item.messages}}"},
        ),
        TestingCriterionAzureAIEvaluator(
            type="azure_ai_evaluator",
            name="groundedness",
            evaluator_name="builtin.groundedness",
            initialization_parameters={"model": model_deployment_name},
            data_mapping={"messages": "{{item.messages}}"},
        ),
    ]

Create evaluation and run

Prep: download sample_data_multiturn_conversations.jsonl

from openai.types.evals.create_eval_jsonl_run_data_source_param import (
    CreateEvalJSONLRunDataSourceParam,
    SourceFileID,
)

# Upload conversation data
data_id = project_client.datasets.upload_file(
    name="multiturn-conversation-data",
    version="1",
    file_path="./sample_data_multiturn_conversations.jsonl",
).id

# Create the evaluation
eval_object = openai_client.evals.create(
    name="Multi-turn Conversation Evaluation",
    data_source_config=data_source_config,
    testing_criteria=testing_criteria,
)

# Create a run with evaluation_level set to "conversation"
eval_run = openai_client.evals.runs.create(
    eval_id=eval_object.id,
    name="multiturn-conversation-run",
    data_source=CreateEvalJSONLRunDataSourceParam(
        type="jsonl",
        source=SourceFileID(
            type="file_id",
            id=data_id,
        ),
    ),
    extra_body={"evaluation_level": "conversation"},
)

To poll for completion and interpret results, see Get cloud evaluation results.

For a complete runnable example, see sample_multiturn_conversation_evaluation.py on GitHub.

Evaluate conversations by ID from traces

Evaluate specific conversations from Application Insights by providing their conversation IDs. Use this option to root-cause problems or verify fixes on specific interactions. For example, you can investigate a conversation flagged by an alert or verify a fix for a known issue.

Where to find conversation IDs

Find conversation IDs in:

  • Application Insights trace logs UI — Browse to interesting traces and locate the conversation_id field in the trace details.
  • Your application's logging output — If you set conversation_id explicitly when creating agent responses, retrieve it from your logs.
  • OpenTelemetry trace context — The conversation_id might also be derived from the traceparent header if your agent uses standard trace context propagation.

Note

Tool definitions are automatically retrieved from the traces or queried from the agent registry. You don't need to provide them in the request.

Parameters for conversation ID lookup

Parameter Required Description
conversation_ids Yes Array of conversation IDs to evaluate.
lookback_hours No Hours to search back from end_time. Defaults to seven days (168 hours).
end_time No End of the search window (ISO 8601 format). Defaults to the current time.
import os
from azure.identity import DefaultAzureCredential
from azure.ai.projects import AIProjectClient
from azure.ai.projects.models import TestingCriterionAzureAIEvaluator

endpoint = os.environ["FOUNDRY_PROJECT_ENDPOINT"]
model_deployment_name = os.environ["FOUNDRY_MODEL_NAME"]

# Provide conversation IDs or trace IDs from App Insights
conversation_ids = ["conversation_1234", "conversation_5678"]

with (
    DefaultAzureCredential() as credential,
    AIProjectClient(endpoint=endpoint, credential=credential) as project_client,
    project_client.get_openai_client() as openai_client,
):
    # Eval group for trace-based evaluations
    data_source_config = {
        "type": "azure_ai_source",
        "scenario": "traces",
    }

    testing_criteria = [
        TestingCriterionAzureAIEvaluator(
            type="azure_ai_evaluator",
            name="customer_satisfaction",
            evaluator_name="builtin.customer_satisfaction",
            initialization_parameters={"model": model_deployment_name},
            data_mapping={"messages": "{{item.messages}}"},
        ),
        TestingCriterionAzureAIEvaluator(
            type="azure_ai_evaluator",
            name="task_completion",
            evaluator_name="builtin.task_completion",
            initialization_parameters={"model": model_deployment_name},
            data_mapping={"messages": "{{item.messages}}"},
        ),
        TestingCriterionAzureAIEvaluator(
            type="azure_ai_evaluator",
            name="conversation_coherence",
            evaluator_name="builtin.coherence",
            initialization_parameters={"model": model_deployment_name},
            data_mapping={"messages": "{{item.messages}}"},
        ),
        TestingCriterionAzureAIEvaluator(
            type="azure_ai_evaluator",
            name="groundedness",
            evaluator_name="builtin.groundedness",
            initialization_parameters={"model": model_deployment_name},
            data_mapping={"messages": "{{item.messages}}"},
        ),
    ]

    # Create evaluation with traces scenario
    eval_object = openai_client.evals.create(
        name="Multi-turn Trace Evaluation (by ID)",
        data_source_config=data_source_config,
        testing_criteria=testing_criteria,
    )

    # Run evaluation on specific conversation IDs
    eval_run = openai_client.evals.runs.create(
        eval_id=eval_object.id,
        name="multiturn-trace-by-id-run",
        data_source={
            "type": "azure_ai_trace_data_source_preview",
            "trace_source": {
                "type": "conversation_id_source",
                "conversation_ids": conversation_ids,
            },
        },
        extra_body={"evaluation_level": "conversation"},
    )

Note

  • Application Insights data ingestion can cause a delay between when traces are generated and when they're available for evaluation. If the query doesn't find traces, wait a few minutes and retry.
  • The maximum lookback is 7 days (168 hours). To access older traces, use start_time and end_time within your App Insights retention limits.

For a complete runnable example, see sample_multiturn_trace_evaluation_by_id.py on GitHub.

Evaluate sampled conversations by agent filter

Evaluate a sampled set of conversations from Application Insights by filtering on agent name. Use this option to assess overall agent quality across production traffic. For example, run regular quality assessments or monitor for quality degradation in production.

The agent you specify for filtering can be part of a multi-agent conversation. The filter matches any conversation where that agent participated.

Note

Tool definitions are automatically retrieved from the traces or queried from the agent registry. You don't need to provide them in the request.

Agent identity fields

Specify the agent to filter by using one of these formats:

Format Example Description
agent_name + agent_version "agent_name": "my-agent", "agent_version": "1" Two separate fields. If agent_version is omitted, use the latest version.
agent_id "agent_id": "my-agent:1" Single string in "name:version" format.

Filter strategies

Strategy Description
random_sampling (Default) Uniformly random sample up to max_traces conversations.
smart_filtering Service-managed heuristic that biases toward "interesting" traces - conversations with potential problems, edge cases, or anomalies.

Parameters

Parameter Required Description
agent_name Yes The agent name to filter traces by.
agent_version No The agent version. If omitted, uses the latest version.
agent_id No Alternative to agent_name + agent_version. Single string in format "name:version".
start_time Yes Start of the time window (Unix epoch seconds, UTC).
end_time Yes End of the time window (Unix epoch seconds, UTC). Pad by +600 seconds to avoid ingestion delay.
max_traces No Maximum conversations to sample. Defaults to 1,000.
filter_strategy No "random_sampling" (default) or "smart_filtering" (service-managed heuristic that biases toward interesting traces).

Important

The time window (end_time - start_time) must be at least 15 minutes (900 seconds). This requirement exists because conversation-level queries apply a 5-minute inactivity buffer on each edge to avoid partial conversations.

import os
import time
from azure.identity import DefaultAzureCredential
from azure.ai.projects import AIProjectClient
from azure.ai.projects.models import TestingCriterionAzureAIEvaluator

endpoint = os.environ["FOUNDRY_PROJECT_ENDPOINT"]
model_deployment_name = os.environ["FOUNDRY_MODEL_NAME"]
agent_name = os.environ["FOUNDRY_AGENT_NAME"]
agent_version = os.environ.get("FOUNDRY_AGENT_VERSION", "")

with (
    DefaultAzureCredential() as credential,
    AIProjectClient(endpoint=endpoint, credential=credential) as project_client,
    project_client.get_openai_client() as openai_client,
):
    # Eval group for trace-based evaluations
    data_source_config = {
        "type": "azure_ai_source",
        "scenario": "traces",
    }

    testing_criteria = [
        TestingCriterionAzureAIEvaluator(
            type="azure_ai_evaluator",
            name="customer_satisfaction",
            evaluator_name="builtin.customer_satisfaction",
            initialization_parameters={"model": model_deployment_name},
            data_mapping={"messages": "{{item.messages}}"},
        ),
        TestingCriterionAzureAIEvaluator(
            type="azure_ai_evaluator",
            name="task_completion",
            evaluator_name="builtin.task_completion",
            initialization_parameters={"model": model_deployment_name},
            data_mapping={"messages": "{{item.messages}}"},
        ),
        TestingCriterionAzureAIEvaluator(
            type="azure_ai_evaluator",
            name="conversation_coherence",
            evaluator_name="builtin.coherence",
            initialization_parameters={"model": model_deployment_name},
            data_mapping={"messages": "{{item.messages}}"},
        ),
        TestingCriterionAzureAIEvaluator(
            type="azure_ai_evaluator",
            name="groundedness",
            evaluator_name="builtin.groundedness",
            initialization_parameters={"model": model_deployment_name},
            data_mapping={"messages": "{{item.messages}}"},
        ),
    ]

    eval_object = openai_client.evals.create(
        name="Multi-turn Trace Evaluation (Agent Filter)",
        data_source_config=data_source_config,
        testing_criteria=testing_criteria,
    )

    # Compute time window in unix seconds
    # Pad end_time by +600s (10 min) to avoid ingestion-delay edge exclusion
    now_unix = int(time.time())
    end_time = now_unix + 600
    start_time = now_unix - (24 * 3600)  # 24 hours lookback

    # Build trace_source with agent filter
    trace_source = {
        "type": "agent_filter",
        "agent_name": agent_name,
        "start_time": start_time,
        "end_time": end_time,
        "max_traces": 5,
    }
    if agent_version:
        trace_source["agent_version"] = agent_version

    # Run evaluation on sampled agent conversations
    eval_run = openai_client.evals.runs.create(
        eval_id=eval_object.id,
        name="multiturn-agent-filter-run",
        data_source={
            "type": "azure_ai_trace_data_source_preview",
            "trace_source": trace_source,
        },
        extra_body={"evaluation_level": "conversation"},
    )

Note

The App Insights query timespan is currently limited to a maximum of 7 days (168 hours). You can't access traces older than 7 days without explicitly providing start_time and end_time within App Insights retention limits.

Next steps