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[P2] Agent platform: structured-output retry + validation hardening #153

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[P2] Agent platform: structured-output retry + validation hardening#153
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Description

@AndresL230
AndresL230
opened on Jun 8, 2026

Part of the Agent migration epic #152 (platform hardening). Owner: Jack.

Goal

Make agent structured-output robust: systematic retry-on-validation and defensive handling so malformed/partial model output and provider schema rejections never surface as raw 500s.

Why

  • The orchestrator-schema-complexity attempt showed Gemini's structured-output API rejects complex schemas before the model even runs — outputs must stay small/flat. That rule is folklore today, not enforced.
  • The audit's agents/LLM pass flagged JSON-mode parsing that can crash on malformed output.

Scope

  • Retry-on-validation: set output_retries (and use ModelRetry) on the agents so a transient invalid output retries instead of failing the request.
  • Codify the output-type rule from the attempt: keep agent output types under ~5 flat fields, prefer enums to constrained strings, no nested optional models. Add a short note in backend/agents/ (or docs/decisions/) so it isn't relearned.
  • Defensive parsing for any remaining raw call_gemini_json paths until they migrate ([P1] Agent migration: document classify/extract step → Pydantic AI agent #143–[P2] Agent migration: remaining one-shot LLM calls (study guide, social, health) → agents/seam #147): guard against non-JSON / partial output.
  • Map failures to clean errors:UnexpectedModelBehavior / UsageLimitExceeded / provider schema-rejection → a typed error response (and the terminal SSE error event on streaming routes), not a raw 500. Reuse the request_id correlation.

Files

backend/agents/*.py (output types + output_retries), backend/agents/_providers.py, backend/services/gemini_service.py (JSON helpers, until retired by #151).

Acceptance

  • A deliberately malformed model output retries and then degrades to a typed error, not a 500 — covered by a test in backend/tests/.
  • Output-type guidance documented and the current agents conform.

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[P2] Agent platform: structured-output retry + validation hardening · Issue #153 · SaplingLearn/Sapling · GitHub
    Skip to content
    [P2] Agent platform: structured-output retry + validation hardening #153
    Closed
    #470
    Closed
    [P2] Agent platform: structured-output retry + validation hardening#153
    #470
    Assignees
    Darkest-Teddy
    Labels
    P2Medium priorityagentsPydantic AI agents / LLM layerbackendBackend / API
    Description
    @AndresL230
    AndresL230
    opened on Jun 8, 2026
    Part of the Agent migration epic #152 (platform hardening). Owner: Jack.
    Goal
    Make agent structured-output robust: systematic retry-on-validation and defensive handling so malformed/partial model output and provider schema rejections never surface as raw 500s.
    Why
    • The orchestrator-schema-complexity attempt showed Gemini's structured-output API rejects complex schemas before the model even runs — outputs must stay small/flat. That rule is folklore today, not enforced.
    • The audit's agents/LLM pass flagged JSON-mode parsing that can crash on malformed output.
    Scope
    • Retry-on-validation: set output_retries (and use ModelRetry) on the agents so a transient invalid output retries instead of failing the request.
    • Codify the output-type rule from the attempt: keep agent output types under ~5 flat fields, prefer enums to constrained strings, no nested optional models. Add a short note in backend/agents/ (or docs/decisions/) so it isn't relearned.
    • Defensive parsing for any remaining raw call_gemini_json paths until they migrate ([P1] Agent migration: document classify/extract step → Pydantic AI agent #143–[P2] Agent migration: remaining one-shot LLM calls (study guide, social, health) → agents/seam #147): guard against non-JSON / partial output.
    • Map failures to clean errors:UnexpectedModelBehavior / UsageLimitExceeded / provider schema-rejection → a typed error response (and the terminal SSE error event on streaming routes), not a raw 500. Reuse the request_id correlation.
    Files
    backend/agents/*.py (output types + output_retries), backend/agents/_providers.py, backend/services/gemini_service.py (JSON helpers, until retired by #151).
    Acceptance
    • A deliberately malformed model output retries and then degrades to a typed error, not a 500 — covered by a test in backend/tests/.
    • Output-type guidance documented and the current agents conform.
    Metadata
    Metadata
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    Labels
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      No branches or pull requests
      Issue actions
      
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[P2] Agent platform: structured-output retry + validation hardening · Issue #153 · SaplingLearn/Sapling · GitHub
      Skip to content
      [P2] Agent platform: structured-output retry + validation hardening #153
      Closed
      #470
      Closed
      [P2] Agent platform: structured-output retry + validation hardening#153
      #470
      Assignees
      Darkest-Teddy
      Labels
      P2Medium priorityagentsPydantic AI agents / LLM layerbackendBackend / API
      Description
      @AndresL230
      AndresL230
      opened on Jun 8, 2026
      Part of the Agent migration epic #152 (platform hardening). Owner: Jack.
      Goal
      Make agent structured-output robust: systematic retry-on-validation and defensive handling so malformed/partial model output and provider schema rejections never surface as raw 500s.
      Why
      • The orchestrator-schema-complexity attempt showed Gemini's structured-output API rejects complex schemas before the model even runs — outputs must stay small/flat. That rule is folklore today, not enforced.
      • The audit's agents/LLM pass flagged JSON-mode parsing that can crash on malformed output.
      Scope
      • Retry-on-validation: set output_retries (and use ModelRetry) on the agents so a transient invalid output retries instead of failing the request.
      • Codify the output-type rule from the attempt: keep agent output types under ~5 flat fields, prefer enums to constrained strings, no nested optional models. Add a short note in backend/agents/ (or docs/decisions/) so it isn't relearned.
      • Defensive parsing for any remaining raw call_gemini_json paths until they migrate ([P1] Agent migration: document classify/extract step → Pydantic AI agent #143–[P2] Agent migration: remaining one-shot LLM calls (study guide, social, health) → agents/seam #147): guard against non-JSON / partial output.
      • Map failures to clean errors:UnexpectedModelBehavior / UsageLimitExceeded / provider schema-rejection → a typed error response (and the terminal SSE error event on streaming routes), not a raw 500. Reuse the request_id correlation.
      Files
      backend/agents/*.py (output types + output_retries), backend/agents/_providers.py, backend/services/gemini_service.py (JSON helpers, until retired by #151).
      Acceptance
      • A deliberately malformed model output retries and then degrades to a typed error, not a 500 — covered by a test in backend/tests/.
      • Output-type guidance documented and the current agents conform.
      Metadata
      Metadata
      Assignees
      Labels
      P2Medium priorityagentsPydantic AI agents / LLM layerbackendBackend / API
      Type
      No type
      Projects
      No projects
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        No milestone
        Relationships
        None yet
        Development
        No branches or pull requests
        Issue actions
        
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[P2] Agent platform: structured-output retry + validation hardening · Issue #153 · SaplingLearn/Sapling · GitHub
        Skip to content
        [P2] Agent platform: structured-output retry + validation hardening #153
        Closed
        #470
        Closed
        [P2] Agent platform: structured-output retry + validation hardening#153
        #470
        Assignees
        Darkest-Teddy
        Labels
        P2Medium priorityagentsPydantic AI agents / LLM layerbackendBackend / API
        Description
        @AndresL230
        AndresL230
        opened on Jun 8, 2026
        Part of the Agent migration epic #152 (platform hardening). Owner: Jack.
        Goal
        Make agent structured-output robust: systematic retry-on-validation and defensive handling so malformed/partial model output and provider schema rejections never surface as raw 500s.
        Why
        • The orchestrator-schema-complexity attempt showed Gemini's structured-output API rejects complex schemas before the model even runs — outputs must stay small/flat. That rule is folklore today, not enforced.
        • The audit's agents/LLM pass flagged JSON-mode parsing that can crash on malformed output.
        Scope
        • Retry-on-validation: set output_retries (and use ModelRetry) on the agents so a transient invalid output retries instead of failing the request.
        • Codify the output-type rule from the attempt: keep agent output types under ~5 flat fields, prefer enums to constrained strings, no nested optional models. Add a short note in backend/agents/ (or docs/decisions/) so it isn't relearned.
        • Defensive parsing for any remaining raw call_gemini_json paths until they migrate ([P1] Agent migration: document classify/extract step → Pydantic AI agent #143–[P2] Agent migration: remaining one-shot LLM calls (study guide, social, health) → agents/seam #147): guard against non-JSON / partial output.
        • Map failures to clean errors:UnexpectedModelBehavior / UsageLimitExceeded / provider schema-rejection → a typed error response (and the terminal SSE error event on streaming routes), not a raw 500. Reuse the request_id correlation.
        Files
        backend/agents/*.py (output types + output_retries), backend/agents/_providers.py, backend/services/gemini_service.py (JSON helpers, until retired by #151).
        Acceptance
        • A deliberately malformed model output retries and then degrades to a typed error, not a 500 — covered by a test in backend/tests/.
        • Output-type guidance documented and the current agents conform.
        Metadata
        Metadata
        Assignees
        Labels
        P2Medium priorityagentsPydantic AI agents / LLM layerbackendBackend / API
        Type
        No type
        Projects
        No projects
          Milestone
          No milestone
          Relationships
          None yet
          Development
          No branches or pull requests
          Issue actions
          
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var __re = new RegExp('^' + "youtube\\.com" + '
[P2] Agent platform: structured-output retry + validation hardening · Issue #153 · SaplingLearn/Sapling · GitHub
          Skip to content
          [P2] Agent platform: structured-output retry + validation hardening #153
          Closed
          #470
          Closed
          [P2] Agent platform: structured-output retry + validation hardening#153
          #470
          Assignees
          Darkest-Teddy
          Labels
          P2Medium priorityagentsPydantic AI agents / LLM layerbackendBackend / API
          Description
          @AndresL230
          AndresL230
          opened on Jun 8, 2026
          Part of the Agent migration epic #152 (platform hardening). Owner: Jack.
          Goal
          Make agent structured-output robust: systematic retry-on-validation and defensive handling so malformed/partial model output and provider schema rejections never surface as raw 500s.
          Why
          • The orchestrator-schema-complexity attempt showed Gemini's structured-output API rejects complex schemas before the model even runs — outputs must stay small/flat. That rule is folklore today, not enforced.
          • The audit's agents/LLM pass flagged JSON-mode parsing that can crash on malformed output.
          Scope
          • Retry-on-validation: set output_retries (and use ModelRetry) on the agents so a transient invalid output retries instead of failing the request.
          • Codify the output-type rule from the attempt: keep agent output types under ~5 flat fields, prefer enums to constrained strings, no nested optional models. Add a short note in backend/agents/ (or docs/decisions/) so it isn't relearned.
          • Defensive parsing for any remaining raw call_gemini_json paths until they migrate ([P1] Agent migration: document classify/extract step → Pydantic AI agent #143–[P2] Agent migration: remaining one-shot LLM calls (study guide, social, health) → agents/seam #147): guard against non-JSON / partial output.
          • Map failures to clean errors:UnexpectedModelBehavior / UsageLimitExceeded / provider schema-rejection → a typed error response (and the terminal SSE error event on streaming routes), not a raw 500. Reuse the request_id correlation.
          Files
          backend/agents/*.py (output types + output_retries), backend/agents/_providers.py, backend/services/gemini_service.py (JSON helpers, until retired by #151).
          Acceptance
          • A deliberately malformed model output retries and then degrades to a typed error, not a 500 — covered by a test in backend/tests/.
          • Output-type guidance documented and the current agents conform.
          Metadata
          Metadata
          Assignees
          Labels
          P2Medium priorityagentsPydantic AI agents / LLM layerbackendBackend / API
          Type
          No type
          Projects
          No projects
            Milestone
            No milestone
            Relationships
            None yet
            Development
            No branches or pull requests
            Issue actions
            
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var __m = "*";
var __re = new RegExp('^' + ".*" + '
[P2] Agent platform: structured-output retry + validation hardening · Issue #153 · SaplingLearn/Sapling · GitHub
            Skip to content
            [P2] Agent platform: structured-output retry + validation hardening #153
            Closed
            #470
            Closed
            [P2] Agent platform: structured-output retry + validation hardening#153
            #470
            Assignees
            Darkest-Teddy
            Labels
            P2Medium priorityagentsPydantic AI agents / LLM layerbackendBackend / API
            Description
            @AndresL230
            AndresL230
            opened on Jun 8, 2026
            Part of the Agent migration epic #152 (platform hardening). Owner: Jack.
            Goal
            Make agent structured-output robust: systematic retry-on-validation and defensive handling so malformed/partial model output and provider schema rejections never surface as raw 500s.
            Why
            • The orchestrator-schema-complexity attempt showed Gemini's structured-output API rejects complex schemas before the model even runs — outputs must stay small/flat. That rule is folklore today, not enforced.
            • The audit's agents/LLM pass flagged JSON-mode parsing that can crash on malformed output.
            Scope
            • Retry-on-validation: set output_retries (and use ModelRetry) on the agents so a transient invalid output retries instead of failing the request.
            • Codify the output-type rule from the attempt: keep agent output types under ~5 flat fields, prefer enums to constrained strings, no nested optional models. Add a short note in backend/agents/ (or docs/decisions/) so it isn't relearned.
            • Defensive parsing for any remaining raw call_gemini_json paths until they migrate ([P1] Agent migration: document classify/extract step → Pydantic AI agent #143–[P2] Agent migration: remaining one-shot LLM calls (study guide, social, health) → agents/seam #147): guard against non-JSON / partial output.
            • Map failures to clean errors:UnexpectedModelBehavior / UsageLimitExceeded / provider schema-rejection → a typed error response (and the terminal SSE error event on streaming routes), not a raw 500. Reuse the request_id correlation.
            Files
            backend/agents/*.py (output types + output_retries), backend/agents/_providers.py, backend/services/gemini_service.py (JSON helpers, until retired by #151).
            Acceptance
            • A deliberately malformed model output retries and then degrades to a typed error, not a 500 — covered by a test in backend/tests/.
            • Output-type guidance documented and the current agents conform.
            Metadata
            Metadata
            Assignees
            Labels
            P2Medium priorityagentsPydantic AI agents / LLM layerbackendBackend / API
            Type
            No type
            Projects
            No projects
              Milestone
              No milestone
              Relationships
              None yet
              Development
              No branches or pull requests
              Issue actions
              
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var __m = "*";
var __re = new RegExp('^' + ".*" + '
[P2] Agent platform: structured-output retry + validation hardening · Issue #153 · SaplingLearn/Sapling · GitHub
              Skip to content
              [P2] Agent platform: structured-output retry + validation hardening #153
              Closed
              #470
              Closed
              [P2] Agent platform: structured-output retry + validation hardening#153
              #470
              Assignees
              Darkest-Teddy
              Labels
              P2Medium priorityagentsPydantic AI agents / LLM layerbackendBackend / API
              Description
              @AndresL230
              AndresL230
              opened on Jun 8, 2026
              Part of the Agent migration epic #152 (platform hardening). Owner: Jack.
              Goal
              Make agent structured-output robust: systematic retry-on-validation and defensive handling so malformed/partial model output and provider schema rejections never surface as raw 500s.
              Why
              • The orchestrator-schema-complexity attempt showed Gemini's structured-output API rejects complex schemas before the model even runs — outputs must stay small/flat. That rule is folklore today, not enforced.
              • The audit's agents/LLM pass flagged JSON-mode parsing that can crash on malformed output.
              Scope
              • Retry-on-validation: set output_retries (and use ModelRetry) on the agents so a transient invalid output retries instead of failing the request.
              • Codify the output-type rule from the attempt: keep agent output types under ~5 flat fields, prefer enums to constrained strings, no nested optional models. Add a short note in backend/agents/ (or docs/decisions/) so it isn't relearned.
              • Defensive parsing for any remaining raw call_gemini_json paths until they migrate ([P1] Agent migration: document classify/extract step → Pydantic AI agent #143–[P2] Agent migration: remaining one-shot LLM calls (study guide, social, health) → agents/seam #147): guard against non-JSON / partial output.
              • Map failures to clean errors:UnexpectedModelBehavior / UsageLimitExceeded / provider schema-rejection → a typed error response (and the terminal SSE error event on streaming routes), not a raw 500. Reuse the request_id correlation.
              Files
              backend/agents/*.py (output types + output_retries), backend/agents/_providers.py, backend/services/gemini_service.py (JSON helpers, until retired by #151).
              Acceptance
              • A deliberately malformed model output retries and then degrades to a typed error, not a 500 — covered by a test in backend/tests/.
              • Output-type guidance documented and the current agents conform.
              Metadata
              Metadata
              Assignees
              Labels
              P2Medium priorityagentsPydantic AI agents / LLM layerbackendBackend / API
              Type
              No type
              Projects
              No projects
                Milestone
                No milestone
                Relationships
                None yet
                Development
                No branches or pull requests
                Issue actions
                
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[P2] Agent platform: structured-output retry + validation hardening · Issue #153 · SaplingLearn/Sapling · GitHub
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                [P2] Agent platform: structured-output retry + validation hardening #153
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                #470
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                [P2] Agent platform: structured-output retry + validation hardening#153
                #470
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                P2Medium priorityagentsPydantic AI agents / LLM layerbackendBackend / API
                Description
                @AndresL230
                AndresL230
                opened on Jun 8, 2026
                Part of the Agent migration epic #152 (platform hardening). Owner: Jack.
                Goal
                Make agent structured-output robust: systematic retry-on-validation and defensive handling so malformed/partial model output and provider schema rejections never surface as raw 500s.
                Why
                • The orchestrator-schema-complexity attempt showed Gemini's structured-output API rejects complex schemas before the model even runs — outputs must stay small/flat. That rule is folklore today, not enforced.
                • The audit's agents/LLM pass flagged JSON-mode parsing that can crash on malformed output.
                Scope
                • Retry-on-validation: set output_retries (and use ModelRetry) on the agents so a transient invalid output retries instead of failing the request.
                • Codify the output-type rule from the attempt: keep agent output types under ~5 flat fields, prefer enums to constrained strings, no nested optional models. Add a short note in backend/agents/ (or docs/decisions/) so it isn't relearned.
                • Defensive parsing for any remaining raw call_gemini_json paths until they migrate ([P1] Agent migration: document classify/extract step → Pydantic AI agent #143–[P2] Agent migration: remaining one-shot LLM calls (study guide, social, health) → agents/seam #147): guard against non-JSON / partial output.
                • Map failures to clean errors:UnexpectedModelBehavior / UsageLimitExceeded / provider schema-rejection → a typed error response (and the terminal SSE error event on streaming routes), not a raw 500. Reuse the request_id correlation.
                Files
                backend/agents/*.py (output types + output_retries), backend/agents/_providers.py, backend/services/gemini_service.py (JSON helpers, until retired by #151).
                Acceptance
                • A deliberately malformed model output retries and then degrades to a typed error, not a 500 — covered by a test in backend/tests/.
                • Output-type guidance documented and the current agents conform.
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