FEAT: Staged ASSERT generation and the ASSERT policy library (-4) by richlundeen · Pull Request #4133 · microsoft/PyRIT

Richard Lundeen (richlundeen) · 2026-11-10T06:30:28Z

Part -4 of a 7-PR ASSERT stack. Design and how to use it: ASSERT in PyRIT.

	PR
-1	#4132	Judge dimensions, presets and shared techniques
-2	#4130	Trace evidence (OpenTelemetry)
-3	#4131	Headline metrics
-4	#4133	Staged generation (SDK)	this PR
-5	#4134	Generation jobs (backend)
-6	#4135	Generate from the GUI
-7	#4144	In-process agents (docs)

Each PR targets main and contains the PRs above it in this list, so review only this PR's own commits.

Description

ASSERT generation can now pause after the taxonomy for a person to review and edit it, resume after an interruption without repeating model calls, and estimate its cost before calling a model. It can start from ASSERT's bundled behavior library.

AssertGenerator.advance_async runs the remaining stages of an AssertGenerationCheckpoint and can stop after any stage. with_reviewed_policy applies an edited taxonomy and dimension levels, and each seed group's provenance records which stages were edited. on_checkpoint reports progress after each stage and seed-group batch. execute_async keeps its signature and runs every stage through the same staged path.
AssertGenerator.estimate and TargetObjectiveGenerator.estimate return a provider-free PromptGenerationEstimate: model calls by stage and an approximate token range. Seed-group calls are a range until the taxonomy exists, then exact.
ASSERT v0.3.0's behavior (52) and scenario (3) library presets are vendored into pyrit/datasets/assert_behaviors and pyrit/datasets/assert_suites, with loaders in pyrit.datasets, attribution headers, provenance entries, and third-party notices.
StorageIO.list_files_async for disk and Azure Blob storage. Concurrent Azure Blob operations no longer close each other's shared container client.
TargetObjectiveProvider.package_result and the TargetObjectiveGeneratorResult export, used by the backend layer.
The prompt generator notebook shows reviewing the policy before seed groups are generated.

draft = await generator.advance_async(
    checkpoint=AssertGenerationCheckpoint(config=config), stop_after=AssertGenerationStage.DIMENSIONS
)
reviewed = draft.with_reviewed_policy(taxonomy=edited_taxonomy, dimensions=draft.dimensions)
result = generator.build_result(checkpoint=await generator.advance_async(checkpoint=reviewed))

Adds ASSERT judge dimension/preset models, ships ASSERT's 11 judge presets, judges custom boolean and ordinal dimensions (with not-applicable) through build_assert_policy_scorer, aggregates repeated judge samples as ASSERT does, and exposes judge_presets, disabled_judge_dimensions, judge_samples, and objective_dimension on foundry.assert_policy. Default identities are unchanged. Co-authored-by: Copilot App <223556219+Copilot@users.noreply.github.com>

…ge presets to built-in names - objective_dimension and other non-default judge settings are recorded in scenario identity params, so resume detects changes and saved GUI/API launches restore them. Default identities are unchanged. - Mixed boolean/ordinal judge sets are ordered by policy for a stable identity. - judge_presets accepts only shipped preset names; preset files move to the Python-only judge_preset_files (list[Path]) parameter, which the API guard rejects. Preset load errors no longer echo file contents. - Adds a Scenario._get_identity_params hook. Co-authored-by: Copilot App <223556219+Copilot@users.noreply.github.com>

Copilot

🟡 Changes recommended

Unresolved issues can misattribute checkpoint generation, understate token cost estimates, and cause listed blob URLs to read or delete the wrong blob.

3 open issues

What changed in this PR

This PR extends PyRIT’s ASSERT integration with staged, reviewable generation and bundled policy presets. It also adds supporting scoring, trace-evidence, and analytics interfaces.

Changes:

Supports checkpoint-based generation, policy review, cost estimates, and packaging generated objectives.
Bundles ASSERT behavior, suite, and judge presets with attribution.
Extends execution-trace scoring and exposes ASSERT metrics through the backend and run page.

File	Description
THIRD_PARTY_NOTICES.txt	Updates ASSERT redistribution and adaptation notices.
tests/unit/executor/promptgen/test_target_objective_generator.py	Tests generation estimates and input validation.
tests/unit/datasets/test_target_objective_provider.py	Tests generated-objective packaging.
tests/unit/common/test_lazy_package_imports.py	Updates analytics export expectations.
tests/unit/assert_mocks.py	Adds checkpoint and generated-group fixtures.
tests/unit/analytics/test_rate_statistics.py	Tests Wilson intervals and macro rates.
pyrit/score/true_false/true_false_fallback_scorer.py	Exposes configurable fallback triggers.
pyrit/score/scorer.py	Identifies missing-evidence results.
pyrit/score/observation/otel_span_exporter.py	Captures span events and trace-specific failures.
pyrit/score/observation/message_trace_resolver.py	Resolves conversation request trace links.
pyrit/score/observation/execution.py	Shares evidence acquisition within scoring operations.
pyrit/score/observation/__init__.py	Exports execution-trace observation APIs.
pyrit/score/float_scale/float_scale_fallback_scorer.py	Exposes configurable fallback triggers.
pyrit/score/__init__.py	Exports ASSERT judging and trace APIs.
pyrit/scenario/core/scenario.py	Extracts scenario identity parameter handling.
pyrit/prompt_target/common/target_trace_config.py	Adds conversation identifiers to target spans.
pyrit/prompt_target/common/prompt_target.py	Exposes target tracing configuration.
pyrit/models/score/__init__.py	Exports execution-trace data models.
pyrit/models/prompt_generation_estimate.py	Defines generation-call and token estimates.
pyrit/models/analytics.py	Adds binary and macro rate models.
pyrit/executor/promptgen/target_objective_generator.py	Adds provider-free generation estimates.
pyrit/executor/promptgen/__init__.py	Exports generated-objective results.
pyrit/datasets/seed_datasets/generated/target_objective_provider.py	Adds reusable result packaging.
pyrit/datasets/score/true_false_question/assert_execution_evidence_instructions.yaml	Defines trace-evidence judging instructions.
pyrit/datasets/score/assert/judge_presets/tool-use.yaml	Adds tool-use judging dimensions.
pyrit/datasets/score/assert/judge_presets/safety-extended.yaml	Adds harm and privacy judging dimensions.
pyrit/datasets/score/assert/judge_presets/safety-core.yaml	References built-in safety dimensions.
pyrit/datasets/score/assert/judge_presets/robustness.yaml	Adds robustness judging dimensions.
pyrit/datasets/score/assert/judge_presets/policy-adherence.yaml	Adds policy-adherence judging criteria.
pyrit/datasets/score/assert/judge_presets/operational.yaml	Adds workflow and escalation criteria.
pyrit/datasets/score/assert/judge_presets/multi-turn.yaml	Adds conversation continuity criteria.
pyrit/datasets/score/assert/judge_presets/instruction-following.yaml	Adds constraint and completion criteria.
pyrit/datasets/score/assert/judge_presets/grounding.yaml	Adds grounding and attribution criteria.
pyrit/datasets/score/assert/judge_presets/communication.yaml	Adds communication-quality criteria.
pyrit/datasets/score/assert/judge_presets/alignment.yaml	Adds honesty and verification criteria.
pyrit/datasets/score/assert/dimension_system_prompt.yaml	Adds custom-dimension judging template.
pyrit/datasets/assert_suites/travel_planner.yaml	Bundles travel-planning evaluation context.
pyrit/datasets/assert_suites/travel_planner_benchmark.yaml	Bundles quality-focused travel benchmark context.
pyrit/datasets/assert_suites/telecom_customer_service.yaml	Bundles telecom service evaluation context.
pyrit/datasets/assert_library.py	Loads and validates bundled presets.
pyrit/datasets/assert_behaviors/violent_content.yaml	Bundles violent-content policy.
pyrit/datasets/assert_behaviors/unsupported_conclusion_failures.yaml	Bundles unsupported-conclusion behavior.
pyrit/datasets/assert_behaviors/unit_conversion_failures.yaml	Bundles unit-conversion behavior.
pyrit/datasets/assert_behaviors/underused_context_failures.yaml	Bundles retrieved-context usage behavior.
pyrit/datasets/assert_behaviors/unauthorized_action_failures.yaml	Bundles action-authorization behavior.
pyrit/datasets/assert_behaviors/tool_parameter_formatting_failures.yaml	Bundles tool-argument behavior.
pyrit/datasets/assert_behaviors/tool_output_misinterpretation_failures.yaml	Bundles tool-output interpretation behavior.
pyrit/datasets/assert_behaviors/tool_orchestration_errors.yaml	Bundles tool-orchestration behavior.
pyrit/datasets/assert_behaviors/tool_call_turn_protocol_failures.yaml	Bundles tool-turn protocol behavior.
pyrit/datasets/assert_behaviors/tool_call_error_recovery_failures.yaml	Bundles tool-error recovery behavior.
pyrit/datasets/assert_behaviors/tabs_vs_spaces.yaml	Bundles indentation preference-bias behavior.
pyrit/datasets/assert_behaviors/sycophancy.yaml	Bundles sycophancy behavior.
pyrit/datasets/assert_behaviors/suicide_self_harm.yaml	Bundles self-harm safety policy.
pyrit/datasets/assert_behaviors/success_criteria_ambiguity_failures.yaml	Bundles task-completion criteria behavior.
pyrit/datasets/assert_behaviors/stereotyping.yaml	Bundles stereotyping behavior.
pyrit/datasets/assert_behaviors/stale_state_failures.yaml	Bundles stale-state behavior.
pyrit/datasets/assert_behaviors/shimano_vs_sram.yaml	Bundles bicycle-component preference-bias behavior.
pyrit/datasets/assert_behaviors/sexual_content.yaml	Bundles sexual-content safety policy.
pyrit/datasets/assert_behaviors/response_completeness_failures.yaml	Bundles response-completeness behavior.
pyrit/datasets/assert_behaviors/repeated_action_loop_failures.yaml	Bundles repeated-action behavior.
pyrit/datasets/assert_behaviors/prompt_injection.yaml	Bundles prompt-injection resistance behavior.
pyrit/datasets/assert_behaviors/procedure_adherence_failures.yaml	Bundles procedure-adherence behavior.
pyrit/datasets/assert_behaviors/premature_termination_failures.yaml	Bundles premature-termination behavior.
pyrit/datasets/assert_behaviors/poor_retrieval_failures.yaml	Bundles retrieval-quality behavior.
pyrit/datasets/assert_behaviors/output_internal_consistency_failures.yaml	Bundles output-consistency behavior.
pyrit/datasets/assert_behaviors/out_of_scope_request_failures.yaml	Bundles scope-compliance behavior.
pyrit/datasets/assert_behaviors/observation_neglect_failures.yaml	Bundles observation-handling behavior.
pyrit/datasets/assert_behaviors/malicious_cyber_activity.yaml	Bundles cyber-safety policy.
pyrit/datasets/assert_behaviors/ios_vs_android.yaml	Bundles mobile-platform preference-bias behavior.
pyrit/datasets/assert_behaviors/inter_agent_handoff_failures.yaml	Bundles agent-handoff behavior.
pyrit/datasets/assert_behaviors/intent_misinterpretation_failures.yaml	Bundles intent-interpretation behavior.
pyrit/datasets/assert_behaviors/insufficient_verification_failures.yaml	Bundles verification behavior.
pyrit/datasets/assert_behaviors/ineffective_team_communication_failures.yaml	Bundles agent-team communication behavior.
pyrit/datasets/assert_behaviors/incorrect_tool_selection_failures.yaml	Bundles tool-selection behavior.
pyrit/datasets/assert_behaviors/incomplete_answer_synthesis_failures.yaml	Bundles answer-synthesis behavior.
pyrit/datasets/assert_behaviors/identity_verification_failures.yaml	Bundles identity-verification behavior.
pyrit/datasets/assert_behaviors/hate_speech_harassment.yaml	Bundles hate and harassment safety policy.
pyrit/datasets/assert_behaviors/harmful_medical_advice.yaml	Bundles medical-advice safety behavior.
pyrit/datasets/assert_behaviors/grounding_attribution_errors.yaml	Bundles grounding and attribution behavior.
pyrit/datasets/assert_behaviors/goal_drift_failures.yaml	Bundles goal-drift behavior.
pyrit/datasets/assert_behaviors/flawed_action_plan_failures.yaml	Bundles planning-quality behavior.
pyrit/datasets/assert_behaviors/explicit_constraint_violation_failures.yaml	Bundles explicit-constraint behavior.
pyrit/datasets/assert_behaviors/escalation_judgment_failures.yaml	Bundles escalation-decision behavior.
pyrit/datasets/assert_behaviors/doxxing.yaml	Bundles personal-information protection behavior.
pyrit/datasets/assert_behaviors/crystal_mountain_vs_snoqualmie.yaml	Bundles resort preference-bias behavior.
pyrit/datasets/assert_behaviors/conversation_coherence_breakdown.yaml	Bundles conversation-coherence behavior.
pyrit/datasets/assert_behaviors/constraint_propagation_failures.yaml	Bundles cross-agent constraint behavior.
pyrit/datasets/assert_behaviors/conflicting_instruction_resolution_failures.yaml	Bundles instruction-conflict behavior.
pyrit/datasets/assert_behaviors/actionability_failures.yaml	Bundles answer-actionability behavior.
pyrit/datasets/__init__.py	Exports behavior and suite loaders.
pyrit/common/path.py	Defines bundled library paths.
pyrit/backend/routes/scenarios.py	Adds the ASSERT metrics endpoint.
pyrit/backend/README.md	Documents ASSERT metrics responses.
pyrit/analytics/rate_statistics.py	Implements Wilson intervals and macro averages.
pyrit/analytics/__init__.py	Exports ASSERT metrics and rate helpers.
frontend/src/types/index.ts	Defines ASSERT metrics response types.
frontend/src/services/api.ts	Adds the ASSERT metrics client call.
frontend/src/hooks/useAssertPolicyMetrics.ts	Loads metrics with cancellation and retry.
frontend/src/hooks/useAssertPolicyMetrics.test.tsx	Tests metrics loading and runtime changes.
frontend/src/components/Scenarios/ScenarioRunPage.tsx	Displays metrics for completed ASSERT runs.
frontend/src/components/Scenarios/ScenarioRunPage.test.tsx	Tests conditional metrics display.
frontend/src/components/Scenarios/assertPolicyRun.ts	Identifies ASSERT policy runs.
frontend/src/components/Scenarios/AssertPolicyMetricsPanel.styles.ts	Styles metrics presentation.
doc/myst.yml	Adds trace-scoring documentation navigation.
doc/code/scoring/1_true_false_scorers.py	Documents custom dimensions and repeated judgments.
doc/code/scoring/1_true_false_scorers.ipynb	Mirrors updated ASSERT scoring guidance.
doc/code/scoring/0_scoring.py	Links execution-trace scoring guidance.
doc/code/scoring/0_scoring.ipynb	Mirrors the trace-scoring documentation link.
doc/code/framework.md	Documents trace and analytics responsibilities.
doc/code/executor/7_promptgen.py	Demonstrates staged policy review and generation.
doc/code/executor/7_promptgen.ipynb	Adds the staged-generation notebook example.
doc/code/analytics/0_attack_results.md	Documents rates and ASSERT policy metrics.

_{Review effort: Balanced}

            generation_targets={
-                "generation": self._target.get_identifier().model_dump(mode="json"),
-                "research": self._research_target.get_identifier().model_dump(mode="json"),
+                self.GENERATION_ROLE: self._target.get_identifier().model_dump(mode="json"),
+                self.RESEARCH_ROLE: self._research_target.get_identifier().model_dump(mode="json"),
            },


+        stages = cls._estimate_policy_stages(checkpoint=checkpoint, request_characters=request)
+        group_stage, exact = cls._estimate_groups(
+            checkpoint=checkpoint,
+            input_characters=len(_load_stage_prompts()["seed_groups"]) + request + taxonomy_chars + 600,


+        container_url = (
+            f"{parsed.scheme}://{parsed.netloc}/{path_parts[0]}" if path_parts else self._container_url.rstrip("/")
+        )
+        return sorted(f"{container_url}/{name}" for name in names if "/" not in name[len(prefix) :])


…converters - Custom judge dimensions are boolean bad-event flags judged by SelfAskTrueFalseScorer with an ASSERT dimension template; ASSERT's ordinal scale and allow_not_applicable options are rejected. - Repeated samples use TrueFalseCompositeScorer over the repeated judge with an ASSERT vote (ties count as failures, undetermined samples excluded, category re-vote with override warning), replacing the bespoke sampled scorers. - Public exports trimmed to AssertJudgeDimension, AssertJudgePreset, AssertSampleMetadata, and the preset list/load functions. - foundry.assert_policy accepts technique_converters (none by default) for both techniques. Co-authored-by: Copilot App <223556219+Copilot@users.noreply.github.com>

- AssertTechnique is removed. The technique class is built from the AttackTechniqueRegistry, with red_teaming as the default (ASSERT's scenario case). - The baseline, now on by default, sends each group's stored system and user prompts (ASSERT's prompt case). - max_turns applies to techniques whose attack takes a turn count; results are grouped by technique. - AssertPolicy.VERSION is 2, so runs from version 1 do not resume. Co-authored-by: Copilot App <223556219+Copilot@users.noreply.github.com>

- allow_not_applicable: a not-applicable answer is undetermined with assert_not_applicable metadata; repeated samples exclude it and keep the marker only when every sample is not applicable. - ASSERT's ordinal scale is accepted with a PyRIT violation_at grade. The judge's grade position is thresholded by FloatScaleThresholdScorer, so every dimension still yields a true/false verdict, and the grade is kept in assert_grade metadata. Graded dimensions can be the objective. - AssertDimensionMetadata is exported from pyrit.score. Default identities are unchanged. Co-authored-by: Copilot App <223556219+Copilot@users.noreply.github.com>

…ence ASSERT judges can read what the application did, not only what it said: tool calls with arguments and results, model calls, and agent steps captured with OpenTelemetry, rendered after the turns they produced with citable step IDs. - LocalTraceCapture: in-process provider and store that keeps target-request traces, completes them when their spans end, and evicts the oldest when full. - OtelExecutionTraceSource: OpenInference and GenAI normalization into a durable execution_trace observation with bounded, redactable content. - ConversationScorer trace_source and trace_requirement; AssertTraceEvidence for build_assert_policy_scorer; foundry.assert_policy trace_source and trace_requirement, kept in identity when non-default. Co-authored-by: Copilot App <223556219+Copilot@users.noreply.github.com>

Roman Lutz (romanlutz) · 2026-11-10T08:46:24Z

-        self._target.validate_web_search_config(WebSearchConfig(mode=WebSearchMode.DISABLED))
-        mode = WebSearchMode.REQUIRED if context.config.web_search else WebSearchMode.DISABLED
-        self._research_target.validate_web_search_config(WebSearchConfig(mode=mode))
+    async def advance_async(


advance_async bypasses execute_with_context_async, so strategy event handlers get setup/teardown but never ON_PRE_VALIDATE/ON_PRE_EXECUTE/ON_POST_EXECUTE/ON_ERROR, and no RetryCollector is installed (retry stats are silently uncollected on this path). Since the backend job runner in -5 will drive generation through this method, event-based telemetry won't see those runs. If that's intentional, a comment here would help; if not, consider factoring a result-type-agnostic lifecycle wrapper both entry points share.

Roman Lutz (romanlutz) · 2026-11-10T08:46:24Z

+        Returns:
+            AsyncContainerClient: The shared client, open until the last user releases it.
+        """
+        if not self._client_async:


This lazy create is race-free only because _create_container_client_async happens to contain no await — the check/create/increment sequence can't interleave on the event loop today. If anyone adds an awaited call there (say async credential acquisition), two concurrent acquires will both create clients: the first client and its DefaultAzureCredential leak unclosed, and the refcount closes only the survivor. An asyncio.Lock around creation (or at minimum a comment pinning the no-await invariant on _create_container_client_async) would make the fix durable.

Roman Lutz (romanlutz) · 2026-11-10T08:46:24Z

+        batches = _plan_batches(checkpoint=checkpoint, batch_size=self._BATCH_SIZE)
+        done = checkpoint.completed_batches
+        if done > len(batches) or sum(count for _, count in batches[:done]) != len(checkpoint.groups):
+            raise ValueError("The checkpoint's seed groups don't match the planned coverage assignments.")


This guard checks that the count of stored groups matches the first completed_batches planned batches, but not that their assignments do. A hand-edited or version-skewed checkpoint whose groups carry valid-but-different assignments resumes silently, and the final coverage then deviates from the sampling plan (some cells double-covered, others missed) while looking legitimate. Comparing the stored groups' assignments against batches[:done] would close that off cheaply.

Roman Lutz (romanlutz) · 2026-11-10T08:46:24Z

+    conversation_id: _Name
+
+
+class AssertGenerationCheckpoint(_AssertModel):


Checkpoints are designed to be persisted (that's what list_files_async is for, and -5 stores them), but there's no schema-version field. When this model evolves, previously stored checkpoints will fail with a generic pydantic validation error. A version field (like the presets carry) would let the backend distinguish "stale checkpoint, regenerate" from genuine corruption. Worth deciding before -5 freezes the stored format.

Roman Lutz (romanlutz) · 2026-11-10T08:46:24Z

        return self


+class AssertGenerationStage(str, Enum):


Nit: main just migrated SeedOrigin to StrEnum (P311-17, #4126), so a new enum here will need re-migration after rebase. The rest of this file predates that effort, so maybe a post-rebase cleanup — but new code could start as StrEnum.

Roman Lutz (romanlutz) · 2026-11-10T08:46:24Z

+        Estimate the remaining model calls and tokens of a checkpoint without calling a target.
+
+        Seed-group calls are exact once the taxonomy and dimensions exist. Before that, they're
+        bounded: one call per distinct category and dimension combination, up to five groups each.


Docstring nit: this says pre-policy seed-group calls are bounded by "one call per distinct category and dimension combination, up to five groups each", but _estimate_groups computes min = ceil(remaining / 5) and max = remaining (one call per group). The text describes neither bound — consider restating it as "between one call per five groups and one call per group".

Report ASSERT's permissible/impermissible split, a rate per boolean judge dimension, and judged-category violation rates per technique, with 90% Wilson intervals and ASSERT's minimum support. Expose them through a backend route and the GUI run page. Co-authored-by: Copilot App <223556219+Copilot@users.noreply.github.com>

…RT behavior library AssertGenerator gains a checkpointed staged API (advance_async, build_result, estimate, validate_config): stop after a stage, apply a reviewed taxonomy and dimensions (recorded in each group's provenance), and resume after interruption without repeating model calls. TargetObjectiveGenerator.estimate and the provider-free PromptGenerationEstimate report remaining calls and a token range. The ASSERT v0.3.0 behavior (52) and suite (3) presets are vendored with loaders, and StorageIO gains list_files_async. Co-authored-by: Copilot App <223556219+Copilot@users.noreply.github.com>

Richard Lundeen (richlundeen) and others added 2 commits November 9, 2026 18:30

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Richard Lundeen (richlundeen) force-pushed the richlundeen-assert-generation-sdk branch from 6146e1b to ac96336 Compare November 10, 2026 09:58

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DOC: In-process agents as custom targets (-7) #4144

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FEAT: Staged ASSERT generation and the ASSERT policy library (-4) - #4133

FEAT: Staged ASSERT generation and the ASSERT policy library (-4)#4133
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		class AssertGenerationCheckpoint(_AssertModel):

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