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Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) #521

Closed
#527
Closed
Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context)#521
#527
Assignees
AndresL230
Labels
P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M

Description

@AndresL230
AndresL230
opened on Aug 3, 2026

Problem

The student's quiz performance record is stored in plaintext:

quiz_attempts.questions_json JSONB -- plaintext: the questions askedquiz_attempts.answers_json JSONB -- plaintext: what the student answeredquiz_context.context_json JSONB NOT NULL-- plaintext: adaptive per-concept history

Neither routes/quiz.py nor any quiz service imports services.encryption — verified by grepping every file that references the module.

Why it matters

This is educational performance data tied to a named student: what they were asked, what they got wrong, and a running model of where they are struggling. It is the same class of content as messages.content (tutor chat) and sessions.summary_json (session summary) — both of which are encrypted. sessions.summary_json is the closest precedent: it is a JSONB summary of learning activity, encrypted with encrypt_json at routes/learn.py:1036.

The questions themselves are also frequently generated from the student's own uploaded course materials, which makes this partly an instance of the derived-content pattern tracked in the sibling issue.

Proposed fix

encrypt_json at write and decrypt_json at read, exactly as sessions.summary_json already does.

Check first:

  • quiz_context.context_json is read on every adaptive quiz generation to build the prompt. Confirm the decrypt happens before the payload reaches the agent, and that the extra round-trip is acceptable on that path.
  • Confirm nothing filters or aggregates on the JSONB contents in SQL. quiz_attempts.score / total / difficulty are separate scalar columns and should stay plaintext so analytics keep working — only the two JSON blobs are in scope.
  • routes/admin_analytics.py rollups: verify they read the scalar columns and not the JSON.

Backfill existing rows via db/backfill_encryption.py, which already has a _encrypt_json_column helper used for documents.concept_notes and sessions.summary_json.

Acceptance

  • quiz_attempts.questions_json, quiz_attempts.answers_json, quiz_context.context_json encrypted via encrypt_json
  • Decrypt before any prompt construction — no ciphertext reaches an LLM call
  • Scalar analytics columns (score, total, difficulty, completed_at) left queryable and confirmed unaffected
  • Backfill extended and run (staging → prod)
  • Raw-SQL round-trip tests per column
  • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated

Parent: see the encryption-coverage epic. Verified against origin/main on 2026-08-02.

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P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M

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var __re = new RegExp('^' + "github\\.com" + '
Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) · Issue #521 · SaplingLearn/Sapling · GitHub
    Skip to content
    Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) #521
    Closed
    #527
    Closed
    Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context)#521
    #527
    Assignees
    AndresL230
    Labels
    P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M
    Description
    @AndresL230
    AndresL230
    opened on Aug 3, 2026
    Problem
    The student's quiz performance record is stored in plaintext:
    quiz_attempts.questions_json JSONB -- plaintext: the questions askedquiz_attempts.answers_json JSONB -- plaintext: what the student answeredquiz_context.context_json JSONB NOT NULL-- plaintext: adaptive per-concept history
    Neither routes/quiz.py nor any quiz service imports services.encryption — verified by grepping every file that references the module.
    Why it matters
    This is educational performance data tied to a named student: what they were asked, what they got wrong, and a running model of where they are struggling. It is the same class of content as messages.content (tutor chat) and sessions.summary_json (session summary) — both of which are encrypted. sessions.summary_json is the closest precedent: it is a JSONB summary of learning activity, encrypted with encrypt_json at routes/learn.py:1036.
    The questions themselves are also frequently generated from the student's own uploaded course materials, which makes this partly an instance of the derived-content pattern tracked in the sibling issue.
    Proposed fix
    encrypt_json at write and decrypt_json at read, exactly as sessions.summary_json already does.
    Check first:
    • quiz_context.context_json is read on every adaptive quiz generation to build the prompt. Confirm the decrypt happens before the payload reaches the agent, and that the extra round-trip is acceptable on that path.
    • Confirm nothing filters or aggregates on the JSONB contents in SQL. quiz_attempts.score / total / difficulty are separate scalar columns and should stay plaintext so analytics keep working — only the two JSON blobs are in scope.
    • routes/admin_analytics.py rollups: verify they read the scalar columns and not the JSON.
    Backfill existing rows via db/backfill_encryption.py, which already has a _encrypt_json_column helper used for documents.concept_notes and sessions.summary_json.
    Acceptance
    • quiz_attempts.questions_json, quiz_attempts.answers_json, quiz_context.context_json encrypted via encrypt_json
    •  Decrypt before any prompt construction — no ciphertext reaches an LLM call
    •  Scalar analytics columns (score, total, difficulty, completed_at) left queryable and confirmed unaffected
    •  Backfill extended and run (staging → prod)
    •  Raw-SQL round-trip tests per column
    • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
    Parent: see the encryption-coverage epic. Verified against origin/main on 2026-08-02.
    Metadata
    Metadata
    Assignees
    Labels
    P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M
    Type
    No type
    Projects
    No projects
      Milestone
      No milestone
      Relationships
      None yet
      Development
      No branches or pull requests
      Issue actions
      
, 'i');
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(function(){
try {
var __m = "*";
var __re = new RegExp('^' + ".*" + '
Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) · Issue #521 · SaplingLearn/Sapling · GitHub
      Skip to content
      Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) #521
      Closed
      #527
      Closed
      Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context)#521
      #527
      Assignees
      AndresL230
      Labels
      P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M
      Description
      @AndresL230
      AndresL230
      opened on Aug 3, 2026
      Problem
      The student's quiz performance record is stored in plaintext:
      quiz_attempts.questions_json JSONB -- plaintext: the questions askedquiz_attempts.answers_json JSONB -- plaintext: what the student answeredquiz_context.context_json JSONB NOT NULL-- plaintext: adaptive per-concept history
      Neither routes/quiz.py nor any quiz service imports services.encryption — verified by grepping every file that references the module.
      Why it matters
      This is educational performance data tied to a named student: what they were asked, what they got wrong, and a running model of where they are struggling. It is the same class of content as messages.content (tutor chat) and sessions.summary_json (session summary) — both of which are encrypted. sessions.summary_json is the closest precedent: it is a JSONB summary of learning activity, encrypted with encrypt_json at routes/learn.py:1036.
      The questions themselves are also frequently generated from the student's own uploaded course materials, which makes this partly an instance of the derived-content pattern tracked in the sibling issue.
      Proposed fix
      encrypt_json at write and decrypt_json at read, exactly as sessions.summary_json already does.
      Check first:
      • quiz_context.context_json is read on every adaptive quiz generation to build the prompt. Confirm the decrypt happens before the payload reaches the agent, and that the extra round-trip is acceptable on that path.
      • Confirm nothing filters or aggregates on the JSONB contents in SQL. quiz_attempts.score / total / difficulty are separate scalar columns and should stay plaintext so analytics keep working — only the two JSON blobs are in scope.
      • routes/admin_analytics.py rollups: verify they read the scalar columns and not the JSON.
      Backfill existing rows via db/backfill_encryption.py, which already has a _encrypt_json_column helper used for documents.concept_notes and sessions.summary_json.
      Acceptance
      • quiz_attempts.questions_json, quiz_attempts.answers_json, quiz_context.context_json encrypted via encrypt_json
      •  Decrypt before any prompt construction — no ciphertext reaches an LLM call
      •  Scalar analytics columns (score, total, difficulty, completed_at) left queryable and confirmed unaffected
      •  Backfill extended and run (staging → prod)
      •  Raw-SQL round-trip tests per column
      • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
      Parent: see the encryption-coverage epic. Verified against origin/main on 2026-08-02.
      Metadata
      Metadata
      Assignees
      Labels
      P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M
      Type
      No type
      Projects
      No projects
        Milestone
        No milestone
        Relationships
        None yet
        Development
        No branches or pull requests
        Issue actions
        
, 'i');
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(function(){
try {
var __m = "*";
var __re = new RegExp('^' + ".*" + '
Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) · Issue #521 · SaplingLearn/Sapling · GitHub
        Skip to content
        Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) #521
        Closed
        #527
        Closed
        Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context)#521
        #527
        Assignees
        AndresL230
        Labels
        P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M
        Description
        @AndresL230
        AndresL230
        opened on Aug 3, 2026
        Problem
        The student's quiz performance record is stored in plaintext:
        quiz_attempts.questions_json JSONB -- plaintext: the questions askedquiz_attempts.answers_json JSONB -- plaintext: what the student answeredquiz_context.context_json JSONB NOT NULL-- plaintext: adaptive per-concept history
        Neither routes/quiz.py nor any quiz service imports services.encryption — verified by grepping every file that references the module.
        Why it matters
        This is educational performance data tied to a named student: what they were asked, what they got wrong, and a running model of where they are struggling. It is the same class of content as messages.content (tutor chat) and sessions.summary_json (session summary) — both of which are encrypted. sessions.summary_json is the closest precedent: it is a JSONB summary of learning activity, encrypted with encrypt_json at routes/learn.py:1036.
        The questions themselves are also frequently generated from the student's own uploaded course materials, which makes this partly an instance of the derived-content pattern tracked in the sibling issue.
        Proposed fix
        encrypt_json at write and decrypt_json at read, exactly as sessions.summary_json already does.
        Check first:
        • quiz_context.context_json is read on every adaptive quiz generation to build the prompt. Confirm the decrypt happens before the payload reaches the agent, and that the extra round-trip is acceptable on that path.
        • Confirm nothing filters or aggregates on the JSONB contents in SQL. quiz_attempts.score / total / difficulty are separate scalar columns and should stay plaintext so analytics keep working — only the two JSON blobs are in scope.
        • routes/admin_analytics.py rollups: verify they read the scalar columns and not the JSON.
        Backfill existing rows via db/backfill_encryption.py, which already has a _encrypt_json_column helper used for documents.concept_notes and sessions.summary_json.
        Acceptance
        • quiz_attempts.questions_json, quiz_attempts.answers_json, quiz_context.context_json encrypted via encrypt_json
        •  Decrypt before any prompt construction — no ciphertext reaches an LLM call
        •  Scalar analytics columns (score, total, difficulty, completed_at) left queryable and confirmed unaffected
        •  Backfill extended and run (staging → prod)
        •  Raw-SQL round-trip tests per column
        • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
        Parent: see the encryption-coverage epic. Verified against origin/main on 2026-08-02.
        Metadata
        Metadata
        Assignees
        Labels
        P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M
        Type
        No type
        Projects
        No projects
          Milestone
          No milestone
          Relationships
          None yet
          Development
          No branches or pull requests
          Issue actions
          
, 'i');
if (__m === '*' || __re.test(location.href)) {
// Strip utm_, fbclid, gclid, etc. from all links on page
(function() {
var trackingParams = ['utm_source', 'utm_medium', 'utm_campaign', 'utm_term', 'utm_content',
'fbclid', 'gclid', 'dclid', 'msclkid', 'yclid',
'ref', 'ref_src', 'source', 'medium', 'campaign'];
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try {
var u = new URL(url, window.location.origin);
var changed = false;
trackingParams.forEach(function(p) {
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});
}
});
});
});
observer.observe(document.body, { childList: true, subtree: true });
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} catch(__e) { console.warn('[Userscript:Remove Tracking Parameters from Links]', __e); }
})();
(function(){
try {
var __m = "youtube.com";
var __re = new RegExp('^' + "youtube\\.com" + '
Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) · Issue #521 · SaplingLearn/Sapling · GitHub
          Skip to content
          Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) #521
          Closed
          #527
          Closed
          Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context)#521
          #527
          Assignees
          AndresL230
          Labels
          P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M
          Description
          @AndresL230
          AndresL230
          opened on Aug 3, 2026
          Problem
          The student's quiz performance record is stored in plaintext:
          quiz_attempts.questions_json JSONB -- plaintext: the questions askedquiz_attempts.answers_json JSONB -- plaintext: what the student answeredquiz_context.context_json JSONB NOT NULL-- plaintext: adaptive per-concept history
          Neither routes/quiz.py nor any quiz service imports services.encryption — verified by grepping every file that references the module.
          Why it matters
          This is educational performance data tied to a named student: what they were asked, what they got wrong, and a running model of where they are struggling. It is the same class of content as messages.content (tutor chat) and sessions.summary_json (session summary) — both of which are encrypted. sessions.summary_json is the closest precedent: it is a JSONB summary of learning activity, encrypted with encrypt_json at routes/learn.py:1036.
          The questions themselves are also frequently generated from the student's own uploaded course materials, which makes this partly an instance of the derived-content pattern tracked in the sibling issue.
          Proposed fix
          encrypt_json at write and decrypt_json at read, exactly as sessions.summary_json already does.
          Check first:
          • quiz_context.context_json is read on every adaptive quiz generation to build the prompt. Confirm the decrypt happens before the payload reaches the agent, and that the extra round-trip is acceptable on that path.
          • Confirm nothing filters or aggregates on the JSONB contents in SQL. quiz_attempts.score / total / difficulty are separate scalar columns and should stay plaintext so analytics keep working — only the two JSON blobs are in scope.
          • routes/admin_analytics.py rollups: verify they read the scalar columns and not the JSON.
          Backfill existing rows via db/backfill_encryption.py, which already has a _encrypt_json_column helper used for documents.concept_notes and sessions.summary_json.
          Acceptance
          • quiz_attempts.questions_json, quiz_attempts.answers_json, quiz_context.context_json encrypted via encrypt_json
          •  Decrypt before any prompt construction — no ciphertext reaches an LLM call
          •  Scalar analytics columns (score, total, difficulty, completed_at) left queryable and confirmed unaffected
          •  Backfill extended and run (staging → prod)
          •  Raw-SQL round-trip tests per column
          • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
          Parent: see the encryption-coverage epic. Verified against origin/main on 2026-08-02.
          Metadata
          Metadata
          Assignees
          Labels
          P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M
          Type
          No type
          Projects
          No projects
            Milestone
            No milestone
            Relationships
            None yet
            Development
            No branches or pull requests
            Issue actions
            
, 'i');
if (__m === '*' || __re.test(location.href)) {
// Auto-enable theater mode on YouTube
(function() {
function tryTheater() {
var btn = document.querySelector('button[aria-label="Theater mode"], ytd-player #player button[title="Theater mode"]');
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tryTheater();
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if (location.href !== lastUrl) {
lastUrl = location.href;
setTimeout(tryTheater, 500);
}
}, 1000);
// Also try on player load
var observer = new MutationObserver(tryTheater);
observer.observe(document.body, { childList: true, subtree: true });
})();
}
} catch(__e) { console.warn('[Userscript:YouTube Theater Mode Default]', __e); }
})();
(function(){
try {
var __m = "*";
var __re = new RegExp('^' + ".*" + '
Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) · Issue #521 · SaplingLearn/Sapling · GitHub
            Skip to content
            Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) #521
            Closed
            #527
            Closed
            Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context)#521
            #527
            Assignees
            AndresL230
            Labels
            P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M
            Description
            @AndresL230
            AndresL230
            opened on Aug 3, 2026
            Problem
            The student's quiz performance record is stored in plaintext:
            quiz_attempts.questions_json JSONB -- plaintext: the questions askedquiz_attempts.answers_json JSONB -- plaintext: what the student answeredquiz_context.context_json JSONB NOT NULL-- plaintext: adaptive per-concept history
            Neither routes/quiz.py nor any quiz service imports services.encryption — verified by grepping every file that references the module.
            Why it matters
            This is educational performance data tied to a named student: what they were asked, what they got wrong, and a running model of where they are struggling. It is the same class of content as messages.content (tutor chat) and sessions.summary_json (session summary) — both of which are encrypted. sessions.summary_json is the closest precedent: it is a JSONB summary of learning activity, encrypted with encrypt_json at routes/learn.py:1036.
            The questions themselves are also frequently generated from the student's own uploaded course materials, which makes this partly an instance of the derived-content pattern tracked in the sibling issue.
            Proposed fix
            encrypt_json at write and decrypt_json at read, exactly as sessions.summary_json already does.
            Check first:
            • quiz_context.context_json is read on every adaptive quiz generation to build the prompt. Confirm the decrypt happens before the payload reaches the agent, and that the extra round-trip is acceptable on that path.
            • Confirm nothing filters or aggregates on the JSONB contents in SQL. quiz_attempts.score / total / difficulty are separate scalar columns and should stay plaintext so analytics keep working — only the two JSON blobs are in scope.
            • routes/admin_analytics.py rollups: verify they read the scalar columns and not the JSON.
            Backfill existing rows via db/backfill_encryption.py, which already has a _encrypt_json_column helper used for documents.concept_notes and sessions.summary_json.
            Acceptance
            • quiz_attempts.questions_json, quiz_attempts.answers_json, quiz_context.context_json encrypted via encrypt_json
            •  Decrypt before any prompt construction — no ciphertext reaches an LLM call
            •  Scalar analytics columns (score, total, difficulty, completed_at) left queryable and confirmed unaffected
            •  Backfill extended and run (staging → prod)
            •  Raw-SQL round-trip tests per column
            • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
            Parent: see the encryption-coverage epic. Verified against origin/main on 2026-08-02.
            Metadata
            Metadata
            Assignees
            Labels
            P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M
            Type
            No type
            Projects
            No projects
              Milestone
              No milestone
              Relationships
              None yet
              Development
              No branches or pull requests
              Issue actions
              
, 'i');
if (__m === '*' || __re.test(location.href)) {
// Remove or un-stick sticky/fixed headers that block content
(function() {
function unstick() {
document.querySelectorAll('header, nav, [role="banner"], .header, .navbar, .sticky, .fixed-top, [style*="position: fixed"], [style*="position:sticky"]').forEach(function(el) {
if (el.style.position === 'fixed' || el.style.position === 'sticky' || getComputedStyle(el).position === 'fixed' || getComputedStyle(el).position === 'sticky') {
el.style.position = 'static';
el.style.top = 'auto';
el.style.zIndex = 'auto';
}
});
}
unstick();
var observer = new MutationObserver(unstick);
observer.observe(document.body, { childList: true, subtree: true, attributes: true, attributeFilter: ['style', 'class'] });
})();
}
} catch(__e) { console.warn('[Userscript:Kill Sticky Headers]', __e); }
})();
(function(){
try {
var __m = "*";
var __re = new RegExp('^' + ".*" + '
Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) · Issue #521 · SaplingLearn/Sapling · GitHub
              Skip to content
              Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) #521
              Closed
              #527
              Closed
              Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context)#521
              #527
              Assignees
              AndresL230
              Labels
              P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M
              Description
              @AndresL230
              AndresL230
              opened on Aug 3, 2026
              Problem
              The student's quiz performance record is stored in plaintext:
              quiz_attempts.questions_json JSONB -- plaintext: the questions askedquiz_attempts.answers_json JSONB -- plaintext: what the student answeredquiz_context.context_json JSONB NOT NULL-- plaintext: adaptive per-concept history
              Neither routes/quiz.py nor any quiz service imports services.encryption — verified by grepping every file that references the module.
              Why it matters
              This is educational performance data tied to a named student: what they were asked, what they got wrong, and a running model of where they are struggling. It is the same class of content as messages.content (tutor chat) and sessions.summary_json (session summary) — both of which are encrypted. sessions.summary_json is the closest precedent: it is a JSONB summary of learning activity, encrypted with encrypt_json at routes/learn.py:1036.
              The questions themselves are also frequently generated from the student's own uploaded course materials, which makes this partly an instance of the derived-content pattern tracked in the sibling issue.
              Proposed fix
              encrypt_json at write and decrypt_json at read, exactly as sessions.summary_json already does.
              Check first:
              • quiz_context.context_json is read on every adaptive quiz generation to build the prompt. Confirm the decrypt happens before the payload reaches the agent, and that the extra round-trip is acceptable on that path.
              • Confirm nothing filters or aggregates on the JSONB contents in SQL. quiz_attempts.score / total / difficulty are separate scalar columns and should stay plaintext so analytics keep working — only the two JSON blobs are in scope.
              • routes/admin_analytics.py rollups: verify they read the scalar columns and not the JSON.
              Backfill existing rows via db/backfill_encryption.py, which already has a _encrypt_json_column helper used for documents.concept_notes and sessions.summary_json.
              Acceptance
              • quiz_attempts.questions_json, quiz_attempts.answers_json, quiz_context.context_json encrypted via encrypt_json
              •  Decrypt before any prompt construction — no ciphertext reaches an LLM call
              •  Scalar analytics columns (score, total, difficulty, completed_at) left queryable and confirmed unaffected
              •  Backfill extended and run (staging → prod)
              •  Raw-SQL round-trip tests per column
              • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
              Parent: see the encryption-coverage epic. Verified against origin/main on 2026-08-02.
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Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) · Issue #521 · SaplingLearn/Sapling · GitHub
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                Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context) #521
                Closed
                #527
                Closed
                Quiz performance data stored in plaintext (questions_json, answers_json, quiz_context)#521
                #527
                Assignees
                AndresL230
                Labels
                P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M
                Description
                @AndresL230
                AndresL230
                opened on Aug 3, 2026
                Problem
                The student's quiz performance record is stored in plaintext:
                quiz_attempts.questions_json JSONB -- plaintext: the questions askedquiz_attempts.answers_json JSONB -- plaintext: what the student answeredquiz_context.context_json JSONB NOT NULL-- plaintext: adaptive per-concept history
                Neither routes/quiz.py nor any quiz service imports services.encryption — verified by grepping every file that references the module.
                Why it matters
                This is educational performance data tied to a named student: what they were asked, what they got wrong, and a running model of where they are struggling. It is the same class of content as messages.content (tutor chat) and sessions.summary_json (session summary) — both of which are encrypted. sessions.summary_json is the closest precedent: it is a JSONB summary of learning activity, encrypted with encrypt_json at routes/learn.py:1036.
                The questions themselves are also frequently generated from the student's own uploaded course materials, which makes this partly an instance of the derived-content pattern tracked in the sibling issue.
                Proposed fix
                encrypt_json at write and decrypt_json at read, exactly as sessions.summary_json already does.
                Check first:
                • quiz_context.context_json is read on every adaptive quiz generation to build the prompt. Confirm the decrypt happens before the payload reaches the agent, and that the extra round-trip is acceptable on that path.
                • Confirm nothing filters or aggregates on the JSONB contents in SQL. quiz_attempts.score / total / difficulty are separate scalar columns and should stay plaintext so analytics keep working — only the two JSON blobs are in scope.
                • routes/admin_analytics.py rollups: verify they read the scalar columns and not the JSON.
                Backfill existing rows via db/backfill_encryption.py, which already has a _encrypt_json_column helper used for documents.concept_notes and sessions.summary_json.
                Acceptance
                • quiz_attempts.questions_json, quiz_attempts.answers_json, quiz_context.context_json encrypted via encrypt_json
                •  Decrypt before any prompt construction — no ciphertext reaches an LLM call
                •  Scalar analytics columns (score, total, difficulty, completed_at) left queryable and confirmed unaffected
                •  Backfill extended and run (staging → prod)
                •  Raw-SQL round-trip tests per column
                • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
                Parent: see the encryption-coverage epic. Verified against origin/main on 2026-08-02.
                Metadata
                Metadata
                Assignees
                Labels
                P2Medium prioritybackendBackend / APIsecuritySecurity / data exposuresize-M
                Type
                No type
                Projects
                No projects
                  Milestone
                  No milestone
                  Relationships
                  None yet
                  Development
                  No branches or pull requests
                  Issue actions