Skip to content

Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) #518

Closed
#528
Closed
Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries)#518
#528
Assignees
AndresL230
Labels
P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L

Description

@AndresL230
AndresL230
opened on Aug 3, 2026

The pattern

Several code paths decrypt protected source material, generate something from it, and then store the derivative in plaintext. The protection on the source is therefore only partial — the same content survives unencrypted one table over.

routes/flashcards.py:17 and routes/study_guide.py:27 make this explicit: both import decrypt_if_present, decrypt_json and nothing else. They read encrypted documents, feed them to the model, and write the output unprotected.

Derived columnSource (encrypted)Written at
flashcards.front / .backdocuments.*routes/flashcards.py:239-240, 400-401
study_guides.content (JSONB)documents.*routes/study_guide.py:201
room_summaries.summaryroom_messages.textservices/social_cache_service.py:34
course_chunks.chunk_textdocuments.extracted_textservices/rag_service.py:209 — tracked separately in #484

sessions.summary_json is encrypted (routes/learn.py:1036), which proves this call has already been made correctly once. These are the instances that were missed.

Scope of this issue

flashcards, study_guides, and room_summaries. course_chunks stays in #484 — but see the note added there about the embedding, because encrypting chunk_text alone does not close it.

Proposed fix

Encrypt at each write boundary and decrypt at each read boundary, using encrypt_if_present for text and encrypt_json for the JSONB payloads, matching notes_service.py and routes/learn.py:1036.

Check before implementing — these are the things that make it more than a find-and-replace:

  • Does anything filter, sort, or join on flashcards.front/back or study_guides.content in SQL? Encrypted columns cannot be queried by value.
  • room_summaries.member_hash is used as a cache key — confirm the summary itself is never compared, only stored and read.
  • Flashcard import (routes/flashcards.py:383, 524) takes cards from the client; encrypt on that path too, not only the generated path.

Backfill existing rows via db/backfill_encryption.py.

Acceptance

  • flashcards.front/back encrypted at write, decrypted at read, on both the generated and imported paths
  • study_guides.content encrypted via encrypt_json
  • room_summaries.summary encrypted at write in social_cache_service.py
  • No SQL path filters or sorts on any newly-encrypted column
  • Backfill extended and run (staging → prod)
  • Raw-SQL round-trip tests per column, matching tests/integration/test_encryption_roundtrip.py
  • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated

Parent: see the encryption-coverage epic. Related: #484. Verified against origin/main on 2026-08-02.

Metadata

Metadata

Assignees

Labels

P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L

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)) { // Add copy buttons to all 
     blocks
(function() {
function addCopyButtons() {
document.querySelectorAll('pre code').forEach(function(codeBlock) {
if (codeBlock.parentElement.hasAttribute('data-copy-added')) return;
codeBlock.parentElement.setAttribute('data-copy-added', 'true');
var btn = document.createElement('button');
btn.textContent = 'Copy';
btn.style.cssText = 'position:absolute;top:4px;right:4px;padding:2px 8px;font-size:11px;background:#4ecdc4;border:none;border-radius:4px;color:#1a1a2e;cursor:pointer;opacity:0.7;transition:opacity 0.2s;';
btn.onmouseover = function() { this.style.opacity = '1'; };
btn.onmouseout = function() { this.style.opacity = '0.7'; };
btn.onclick = function() {
navigator.clipboard.writeText(codeBlock.textContent).then(function() {
btn.textContent = 'Copied!';
setTimeout(function() { btn.textContent = 'Copy'; }, 1500);
});
};
codeBlock.parentElement.style.position = 'relative';
codeBlock.parentElement.appendChild(btn);
});
}
addCopyButtons();
// Re-run on dynamic content
var observer = new MutationObserver(addCopyButtons);
observer.observe(document.body, { childList: true, subtree: true });
})();
}
} catch(__e) { console.warn('[Userscript:Add Copy Buttons to Code Blocks]', __e); }
})();
(function(){
try {
var __m = "github.com";
var __re = new RegExp('^' + "github\\.com" + '
Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) · Issue #518 · SaplingLearn/Sapling · GitHub
    Skip to content
    Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) #518
    Closed
    #528
    Closed
    Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries)#518
    #528
    Assignees
    AndresL230
    Labels
    P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
    Description
    @AndresL230
    AndresL230
    opened on Aug 3, 2026
    The pattern
    Several code paths decrypt protected source material, generate something from it, and then store the derivative in plaintext. The protection on the source is therefore only partial — the same content survives unencrypted one table over.
    routes/flashcards.py:17 and routes/study_guide.py:27 make this explicit: both import decrypt_if_present, decrypt_json and nothing else. They read encrypted documents, feed them to the model, and write the output unprotected.
    Derived columnSource (encrypted)Written at
    flashcards.front / .backdocuments.*routes/flashcards.py:239-240, 400-401
    study_guides.content (JSONB)documents.*routes/study_guide.py:201
    room_summaries.summaryroom_messages.textservices/social_cache_service.py:34
    course_chunks.chunk_textdocuments.extracted_textservices/rag_service.py:209 — tracked separately in #484
    sessions.summary_json is encrypted (routes/learn.py:1036), which proves this call has already been made correctly once. These are the instances that were missed.
    Scope of this issue
    flashcards, study_guides, and room_summaries. course_chunks stays in #484 — but see the note added there about the embedding, because encrypting chunk_text alone does not close it.
    Proposed fix
    Encrypt at each write boundary and decrypt at each read boundary, using encrypt_if_present for text and encrypt_json for the JSONB payloads, matching notes_service.py and routes/learn.py:1036.
    Check before implementing — these are the things that make it more than a find-and-replace:
    • Does anything filter, sort, or join on flashcards.front/back or study_guides.content in SQL? Encrypted columns cannot be queried by value.
    • room_summaries.member_hash is used as a cache key — confirm the summary itself is never compared, only stored and read.
    • Flashcard import (routes/flashcards.py:383, 524) takes cards from the client; encrypt on that path too, not only the generated path.
    Backfill existing rows via db/backfill_encryption.py.
    Acceptance
    • flashcards.front/back encrypted at write, decrypted at read, on both the generated and imported paths
    • study_guides.content encrypted via encrypt_json
    • room_summaries.summary encrypted at write in social_cache_service.py
    •  No SQL path filters or sorts on any newly-encrypted column
    •  Backfill extended and run (staging → prod)
    •  Raw-SQL round-trip tests per column, matching tests/integration/test_encryption_roundtrip.py
    • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
    Parent: see the encryption-coverage epic. Related: #484. Verified against origin/main on 2026-08-02.
    Metadata
    Metadata
    Assignees
    Labels
    P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
    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)) {
// Force GitHub README to respect dark mode
(function() {
var style = document.createElement('style');
style.textContent = '
.markdown-body {
color-scheme: dark light;
}
.markdown-body pre { background: #161b22 !important; }
.markdown-body code { background: rgba(110, 118, 129, 0.4) !important; }
.markdown-body table th, .markdown-body table td { border-color: #30363d !important; }
.markdown-body img { background: #0d1117; }
.markdown-body blockquote { border-left-color: #8b949e; }
.markdown-body hr { border-color: #30363d; }
';
document.head.appendChild(style);
})();
}
} catch(__e) { console.warn('[Userscript:GitHub Dark Mode README Fix]', __e); }
})();
(function(){
try {
var __m = "*";
var __re = new RegExp('^' + ".*" + '
Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) · Issue #518 · SaplingLearn/Sapling · GitHub
      Skip to content
      Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) #518
      Closed
      #528
      Closed
      Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries)#518
      #528
      Assignees
      AndresL230
      Labels
      P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
      Description
      @AndresL230
      AndresL230
      opened on Aug 3, 2026
      The pattern
      Several code paths decrypt protected source material, generate something from it, and then store the derivative in plaintext. The protection on the source is therefore only partial — the same content survives unencrypted one table over.
      routes/flashcards.py:17 and routes/study_guide.py:27 make this explicit: both import decrypt_if_present, decrypt_json and nothing else. They read encrypted documents, feed them to the model, and write the output unprotected.
      Derived columnSource (encrypted)Written at
      flashcards.front / .backdocuments.*routes/flashcards.py:239-240, 400-401
      study_guides.content (JSONB)documents.*routes/study_guide.py:201
      room_summaries.summaryroom_messages.textservices/social_cache_service.py:34
      course_chunks.chunk_textdocuments.extracted_textservices/rag_service.py:209 — tracked separately in #484
      sessions.summary_json is encrypted (routes/learn.py:1036), which proves this call has already been made correctly once. These are the instances that were missed.
      Scope of this issue
      flashcards, study_guides, and room_summaries. course_chunks stays in #484 — but see the note added there about the embedding, because encrypting chunk_text alone does not close it.
      Proposed fix
      Encrypt at each write boundary and decrypt at each read boundary, using encrypt_if_present for text and encrypt_json for the JSONB payloads, matching notes_service.py and routes/learn.py:1036.
      Check before implementing — these are the things that make it more than a find-and-replace:
      • Does anything filter, sort, or join on flashcards.front/back or study_guides.content in SQL? Encrypted columns cannot be queried by value.
      • room_summaries.member_hash is used as a cache key — confirm the summary itself is never compared, only stored and read.
      • Flashcard import (routes/flashcards.py:383, 524) takes cards from the client; encrypt on that path too, not only the generated path.
      Backfill existing rows via db/backfill_encryption.py.
      Acceptance
      • flashcards.front/back encrypted at write, decrypted at read, on both the generated and imported paths
      • study_guides.content encrypted via encrypt_json
      • room_summaries.summary encrypted at write in social_cache_service.py
      •  No SQL path filters or sorts on any newly-encrypted column
      •  Backfill extended and run (staging → prod)
      •  Raw-SQL round-trip tests per column, matching tests/integration/test_encryption_roundtrip.py
      • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
      Parent: see the encryption-coverage epic. Related: #484. Verified against origin/main on 2026-08-02.
      Metadata
      Metadata
      Assignees
      Labels
      P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
      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)) {
// Highlight search terms from Google/DuckDuckGo/Bing referrer
(function() {
var ref = document.referrer;
var terms = [];
if (ref.includes('google.com') || ref.includes('duckduckgo.com') || ref.includes('bing.com')) {
var url = new URL(ref);
var q = url.searchParams.get('q') || url.searchParams.get('p');
if (q) {
terms = q.split(/\s+/).filter(function(t) { return t.length > 2; });
}
}
if (terms.length === 0) return;
var style = document.createElement('style');
style.textContent = '.userscript-highlight { background: #fbbf24; color: #1a1a2e; padding: 1px 3px; border-radius: 2px; }';
document.head.appendChild(style);
function highlight(node) {
if (node.nodeType === 3) { // text node
var text = node.textContent;
var found = false;
terms.forEach(function(term) {
var regex = new RegExp('(' + term.replace(/[.*+?^${}()|[\]\\]/g, '\\') + ')', 'gi');
if (regex.test(text)) {
found = true;
var frag = document.createDocumentFragment();
var parts = text.split(regex);
parts.forEach(function(part, i) {
if (i % 2 === 0) {
frag.appendChild(document.createTextNode(part));
} else {
var span = document.createElement('span');
span.className = 'userscript-highlight';
span.textContent = part;
frag.appendChild(span);
}
});
node.parentNode.replaceChild(frag, node);
}
});
} else if (node.nodeType === 1 && node.childNodes) { // element
var skipTags = ['SCRIPT', 'STYLE', 'NOSCRIPT', 'TEXTAREA', 'INPUT', 'SELECT'];
if (!skipTags.includes(node.tagName)) {
Array.from(node.childNodes).forEach(highlight);
}
}
}
highlight(document.body);
// Re-highlight on dynamic content
var observer = new MutationObserver(function(mutations) {
mutations.forEach(function(m) {
m.addedNodes.forEach(function(node) {
if (node.nodeType === 1 || node.nodeType === 3) highlight(node);
});
});
});
observer.observe(document.body, { childList: true, subtree: true });
})();
}
} catch(__e) { console.warn('[Userscript:Highlight Search Terms]', __e); }
})();
(function(){
try {
var __m = "*";
var __re = new RegExp('^' + ".*" + '
Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) · Issue #518 · SaplingLearn/Sapling · GitHub
        Skip to content
        Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) #518
        Closed
        #528
        Closed
        Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries)#518
        #528
        Assignees
        AndresL230
        Labels
        P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
        Description
        @AndresL230
        AndresL230
        opened on Aug 3, 2026
        The pattern
        Several code paths decrypt protected source material, generate something from it, and then store the derivative in plaintext. The protection on the source is therefore only partial — the same content survives unencrypted one table over.
        routes/flashcards.py:17 and routes/study_guide.py:27 make this explicit: both import decrypt_if_present, decrypt_json and nothing else. They read encrypted documents, feed them to the model, and write the output unprotected.
        Derived columnSource (encrypted)Written at
        flashcards.front / .backdocuments.*routes/flashcards.py:239-240, 400-401
        study_guides.content (JSONB)documents.*routes/study_guide.py:201
        room_summaries.summaryroom_messages.textservices/social_cache_service.py:34
        course_chunks.chunk_textdocuments.extracted_textservices/rag_service.py:209 — tracked separately in #484
        sessions.summary_json is encrypted (routes/learn.py:1036), which proves this call has already been made correctly once. These are the instances that were missed.
        Scope of this issue
        flashcards, study_guides, and room_summaries. course_chunks stays in #484 — but see the note added there about the embedding, because encrypting chunk_text alone does not close it.
        Proposed fix
        Encrypt at each write boundary and decrypt at each read boundary, using encrypt_if_present for text and encrypt_json for the JSONB payloads, matching notes_service.py and routes/learn.py:1036.
        Check before implementing — these are the things that make it more than a find-and-replace:
        • Does anything filter, sort, or join on flashcards.front/back or study_guides.content in SQL? Encrypted columns cannot be queried by value.
        • room_summaries.member_hash is used as a cache key — confirm the summary itself is never compared, only stored and read.
        • Flashcard import (routes/flashcards.py:383, 524) takes cards from the client; encrypt on that path too, not only the generated path.
        Backfill existing rows via db/backfill_encryption.py.
        Acceptance
        • flashcards.front/back encrypted at write, decrypted at read, on both the generated and imported paths
        • study_guides.content encrypted via encrypt_json
        • room_summaries.summary encrypted at write in social_cache_service.py
        •  No SQL path filters or sorts on any newly-encrypted column
        •  Backfill extended and run (staging → prod)
        •  Raw-SQL round-trip tests per column, matching tests/integration/test_encryption_roundtrip.py
        • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
        Parent: see the encryption-coverage epic. Related: #484. Verified against origin/main on 2026-08-02.
        Metadata
        Metadata
        Assignees
        Labels
        P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
        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'];
function cleanUrl(url) {
try {
var u = new URL(url, window.location.origin);
var changed = false;
trackingParams.forEach(function(p) {
if (u.searchParams.has(p)) {
u.searchParams.delete(p);
changed = true;
}
});
return changed ? u.toString() : url;
} catch (e) {
return url;
}
}
function cleanLinks() {
document.querySelectorAll('a[href]').forEach(function(a) {
var clean = cleanUrl(a.href);
if (clean !== a.href) a.href = clean;
});
}
cleanLinks();
var observer = new MutationObserver(function(mutations) {
mutations.forEach(function(m) {
m.addedNodes.forEach(function(node) {
if (node.nodeType === 1) {
if (node.tagName === 'A') cleanLinks();
node.querySelectorAll('a[href]').forEach(function(a) {
var clean = cleanUrl(a.href);
if (clean !== a.href) a.href = clean;
});
}
});
});
});
observer.observe(document.body, { childList: true, subtree: true });
})();
}
} catch(__e) { console.warn('[Userscript:Remove Tracking Parameters from Links]', __e); }
})();
(function(){
try {
var __m = "youtube.com";
var __re = new RegExp('^' + "youtube\\.com" + '
Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) · Issue #518 · SaplingLearn/Sapling · GitHub
          Skip to content
          Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) #518
          Closed
          #528
          Closed
          Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries)#518
          #528
          Assignees
          AndresL230
          Labels
          P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
          Description
          @AndresL230
          AndresL230
          opened on Aug 3, 2026
          The pattern
          Several code paths decrypt protected source material, generate something from it, and then store the derivative in plaintext. The protection on the source is therefore only partial — the same content survives unencrypted one table over.
          routes/flashcards.py:17 and routes/study_guide.py:27 make this explicit: both import decrypt_if_present, decrypt_json and nothing else. They read encrypted documents, feed them to the model, and write the output unprotected.
          Derived columnSource (encrypted)Written at
          flashcards.front / .backdocuments.*routes/flashcards.py:239-240, 400-401
          study_guides.content (JSONB)documents.*routes/study_guide.py:201
          room_summaries.summaryroom_messages.textservices/social_cache_service.py:34
          course_chunks.chunk_textdocuments.extracted_textservices/rag_service.py:209 — tracked separately in #484
          sessions.summary_json is encrypted (routes/learn.py:1036), which proves this call has already been made correctly once. These are the instances that were missed.
          Scope of this issue
          flashcards, study_guides, and room_summaries. course_chunks stays in #484 — but see the note added there about the embedding, because encrypting chunk_text alone does not close it.
          Proposed fix
          Encrypt at each write boundary and decrypt at each read boundary, using encrypt_if_present for text and encrypt_json for the JSONB payloads, matching notes_service.py and routes/learn.py:1036.
          Check before implementing — these are the things that make it more than a find-and-replace:
          • Does anything filter, sort, or join on flashcards.front/back or study_guides.content in SQL? Encrypted columns cannot be queried by value.
          • room_summaries.member_hash is used as a cache key — confirm the summary itself is never compared, only stored and read.
          • Flashcard import (routes/flashcards.py:383, 524) takes cards from the client; encrypt on that path too, not only the generated path.
          Backfill existing rows via db/backfill_encryption.py.
          Acceptance
          • flashcards.front/back encrypted at write, decrypted at read, on both the generated and imported paths
          • study_guides.content encrypted via encrypt_json
          • room_summaries.summary encrypted at write in social_cache_service.py
          •  No SQL path filters or sorts on any newly-encrypted column
          •  Backfill extended and run (staging → prod)
          •  Raw-SQL round-trip tests per column, matching tests/integration/test_encryption_roundtrip.py
          • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
          Parent: see the encryption-coverage epic. Related: #484. Verified against origin/main on 2026-08-02.
          Metadata
          Metadata
          Assignees
          Labels
          P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
          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"]');
if (btn && !btn.classList.contains('activated')) {
btn.click();
}
}
// Try immediately
tryTheater();
// Try after navigation (SPA)
var lastUrl = location.href;
setInterval(function() {
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('^' + ".*" + '
Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) · Issue #518 · SaplingLearn/Sapling · GitHub
            Skip to content
            Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) #518
            Closed
            #528
            Closed
            Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries)#518
            #528
            Assignees
            AndresL230
            Labels
            P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
            Description
            @AndresL230
            AndresL230
            opened on Aug 3, 2026
            The pattern
            Several code paths decrypt protected source material, generate something from it, and then store the derivative in plaintext. The protection on the source is therefore only partial — the same content survives unencrypted one table over.
            routes/flashcards.py:17 and routes/study_guide.py:27 make this explicit: both import decrypt_if_present, decrypt_json and nothing else. They read encrypted documents, feed them to the model, and write the output unprotected.
            Derived columnSource (encrypted)Written at
            flashcards.front / .backdocuments.*routes/flashcards.py:239-240, 400-401
            study_guides.content (JSONB)documents.*routes/study_guide.py:201
            room_summaries.summaryroom_messages.textservices/social_cache_service.py:34
            course_chunks.chunk_textdocuments.extracted_textservices/rag_service.py:209 — tracked separately in #484
            sessions.summary_json is encrypted (routes/learn.py:1036), which proves this call has already been made correctly once. These are the instances that were missed.
            Scope of this issue
            flashcards, study_guides, and room_summaries. course_chunks stays in #484 — but see the note added there about the embedding, because encrypting chunk_text alone does not close it.
            Proposed fix
            Encrypt at each write boundary and decrypt at each read boundary, using encrypt_if_present for text and encrypt_json for the JSONB payloads, matching notes_service.py and routes/learn.py:1036.
            Check before implementing — these are the things that make it more than a find-and-replace:
            • Does anything filter, sort, or join on flashcards.front/back or study_guides.content in SQL? Encrypted columns cannot be queried by value.
            • room_summaries.member_hash is used as a cache key — confirm the summary itself is never compared, only stored and read.
            • Flashcard import (routes/flashcards.py:383, 524) takes cards from the client; encrypt on that path too, not only the generated path.
            Backfill existing rows via db/backfill_encryption.py.
            Acceptance
            • flashcards.front/back encrypted at write, decrypted at read, on both the generated and imported paths
            • study_guides.content encrypted via encrypt_json
            • room_summaries.summary encrypted at write in social_cache_service.py
            •  No SQL path filters or sorts on any newly-encrypted column
            •  Backfill extended and run (staging → prod)
            •  Raw-SQL round-trip tests per column, matching tests/integration/test_encryption_roundtrip.py
            • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
            Parent: see the encryption-coverage epic. Related: #484. Verified against origin/main on 2026-08-02.
            Metadata
            Metadata
            Assignees
            Labels
            P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
            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('^' + ".*" + '
Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) · Issue #518 · SaplingLearn/Sapling · GitHub
              Skip to content
              Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) #518
              Closed
              #528
              Closed
              Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries)#518
              #528
              Assignees
              AndresL230
              Labels
              P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
              Description
              @AndresL230
              AndresL230
              opened on Aug 3, 2026
              The pattern
              Several code paths decrypt protected source material, generate something from it, and then store the derivative in plaintext. The protection on the source is therefore only partial — the same content survives unencrypted one table over.
              routes/flashcards.py:17 and routes/study_guide.py:27 make this explicit: both import decrypt_if_present, decrypt_json and nothing else. They read encrypted documents, feed them to the model, and write the output unprotected.
              Derived columnSource (encrypted)Written at
              flashcards.front / .backdocuments.*routes/flashcards.py:239-240, 400-401
              study_guides.content (JSONB)documents.*routes/study_guide.py:201
              room_summaries.summaryroom_messages.textservices/social_cache_service.py:34
              course_chunks.chunk_textdocuments.extracted_textservices/rag_service.py:209 — tracked separately in #484
              sessions.summary_json is encrypted (routes/learn.py:1036), which proves this call has already been made correctly once. These are the instances that were missed.
              Scope of this issue
              flashcards, study_guides, and room_summaries. course_chunks stays in #484 — but see the note added there about the embedding, because encrypting chunk_text alone does not close it.
              Proposed fix
              Encrypt at each write boundary and decrypt at each read boundary, using encrypt_if_present for text and encrypt_json for the JSONB payloads, matching notes_service.py and routes/learn.py:1036.
              Check before implementing — these are the things that make it more than a find-and-replace:
              • Does anything filter, sort, or join on flashcards.front/back or study_guides.content in SQL? Encrypted columns cannot be queried by value.
              • room_summaries.member_hash is used as a cache key — confirm the summary itself is never compared, only stored and read.
              • Flashcard import (routes/flashcards.py:383, 524) takes cards from the client; encrypt on that path too, not only the generated path.
              Backfill existing rows via db/backfill_encryption.py.
              Acceptance
              • flashcards.front/back encrypted at write, decrypted at read, on both the generated and imported paths
              • study_guides.content encrypted via encrypt_json
              • room_summaries.summary encrypted at write in social_cache_service.py
              •  No SQL path filters or sorts on any newly-encrypted column
              •  Backfill extended and run (staging → prod)
              •  Raw-SQL round-trip tests per column, matching tests/integration/test_encryption_roundtrip.py
              • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
              Parent: see the encryption-coverage epic. Related: #484. Verified against origin/main on 2026-08-02.
              Metadata
              Metadata
              Assignees
              Labels
              P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
              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)) {
// Universal Dark Mode - works on any site
(function() {
var enabled = true;
function applyDarkMode() {
if (!enabled) return;
// Create style element if it doesn't exist
var style = document.getElementById('universal-dark-mode-style');
if (!style) {
style = document.createElement('style');
style.id = 'universal-dark-mode-style';
document.head.appendChild(style);
}
// Dark mode CSS - inverts colors but preserves images/video
style.textContent = '
/* Invert everything except media */
html {
filter: invert(1) hue-rotate(180deg) !important;
background: #1a1a2e !important;
}
/* Restore images, videos, iframes, canvas */
img, video, iframe, canvas, svg, picture, [style*="background-image"] {
filter: invert(1) hue-rotate(180deg) !important;
}
/* Preserve specific elements that should not be inverted */
.no-dark-mode, .no-dark-mode *,
[data-theme="light"], [data-theme="light"],
.ace_editor, .ace_editor *,
.CodeMirror, .CodeMirror *,
.monaco-editor, .monaco-editor *,
.markdown-body pre, .markdown-body pre *,
.highlight, .highlight *,
pre code, pre code * {
filter: none !important;
}
/* Fix common UI elements */
.modal, .popup, .dropdown-menu, .tooltip, .popover {
filter: invert(1) hue-rotate(180deg) !important;
background: #2d2d44 !important;
border-color: #444 !important;
}
/* Scrollbars */
::-webkit-scrollbar { background: #1a1a2e !important; }
::-webkit-scrollbar-thumb { background: #444 !important; }
::-webkit-scrollbar-thumb:hover { background: #555 !important; }
/* Selection */
::selection { background: #4ecdc4 !important; color: #1a1a2e !important; }
::-moz-selection { background: #4ecdc4 !important; color: #1a1a2e !important; }
';
}
function removeDarkMode() {
var style = document.getElementById('universal-dark-mode-style');
if (style) style.remove();
}
// Toggle with Alt+Shift+D
document.addEventListener('keydown', function(e) {
if (e.altKey && e.shiftKey && e.key === 'D') {
e.preventDefault();
enabled = !enabled;
if (enabled) {
applyDarkMode();
console.log('[Universal Dark Mode] Enabled');
} else {
removeDarkMode();
console.log('[Universal Dark Mode] Disabled');
}
}
});
// Apply on load
applyDarkMode();
// Re-apply on dynamic content
var observer = new MutationObserver(function(mutations) {
if (enabled && !document.getElementById('universal-dark-mode-style')) {
applyDarkMode();
}
});
observer.observe(document.head, { childList: true });
console.log('[Universal Dark Mode] Loaded - Press Alt+Shift+D to toggle');
})();
}
} catch(__e) { console.warn('[Userscript:Universal Dark Mode]', __e); }
})();
})();
Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) · Issue #518 · SaplingLearn/Sapling · GitHub
                Skip to content
                Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries) #518
                Closed
                #528
                Closed
                Derived content is stored in plaintext while its encrypted source is protected (flashcards, study guides, room summaries)#518
                #528
                Assignees
                AndresL230
                Labels
                P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
                Description
                @AndresL230
                AndresL230
                opened on Aug 3, 2026
                The pattern
                Several code paths decrypt protected source material, generate something from it, and then store the derivative in plaintext. The protection on the source is therefore only partial — the same content survives unencrypted one table over.
                routes/flashcards.py:17 and routes/study_guide.py:27 make this explicit: both import decrypt_if_present, decrypt_json and nothing else. They read encrypted documents, feed them to the model, and write the output unprotected.
                Derived columnSource (encrypted)Written at
                flashcards.front / .backdocuments.*routes/flashcards.py:239-240, 400-401
                study_guides.content (JSONB)documents.*routes/study_guide.py:201
                room_summaries.summaryroom_messages.textservices/social_cache_service.py:34
                course_chunks.chunk_textdocuments.extracted_textservices/rag_service.py:209 — tracked separately in #484
                sessions.summary_json is encrypted (routes/learn.py:1036), which proves this call has already been made correctly once. These are the instances that were missed.
                Scope of this issue
                flashcards, study_guides, and room_summaries. course_chunks stays in #484 — but see the note added there about the embedding, because encrypting chunk_text alone does not close it.
                Proposed fix
                Encrypt at each write boundary and decrypt at each read boundary, using encrypt_if_present for text and encrypt_json for the JSONB payloads, matching notes_service.py and routes/learn.py:1036.
                Check before implementing — these are the things that make it more than a find-and-replace:
                • Does anything filter, sort, or join on flashcards.front/back or study_guides.content in SQL? Encrypted columns cannot be queried by value.
                • room_summaries.member_hash is used as a cache key — confirm the summary itself is never compared, only stored and read.
                • Flashcard import (routes/flashcards.py:383, 524) takes cards from the client; encrypt on that path too, not only the generated path.
                Backfill existing rows via db/backfill_encryption.py.
                Acceptance
                • flashcards.front/back encrypted at write, decrypted at read, on both the generated and imported paths
                • study_guides.content encrypted via encrypt_json
                • room_summaries.summary encrypted at write in social_cache_service.py
                •  No SQL path filters or sorts on any newly-encrypted column
                •  Backfill extended and run (staging → prod)
                •  Raw-SQL round-trip tests per column, matching tests/integration/test_encryption_roundtrip.py
                • CLAUDE.md + Canopy sapling-infrastructure encrypted-columns table updated
                Parent: see the encryption-coverage epic. Related: #484. Verified against origin/main on 2026-08-02.
                Metadata
                Metadata
                Assignees
                Labels
                P2Medium prioritybackendBackend / APIdata-integrityCorrectness of stored/served datasecuritySecurity / data exposuresize-L
                Type
                No type
                Projects
                No projects
                  Milestone
                  No milestone
                  Relationships
                  None yet
                  Development
                  No branches or pull requests
                  Issue actions