newsletter_emails.email is plaintext while users.email is encrypted — needs a decision, not a swap #519

Description

@AndresL230

Problem

newsletter_emails.email is stored in plaintext, while users.emailis encrypted (routes/auth.py:477,508). Same data type, same sensitivity, two different answers. 4 rows in production.

CREATETABLEIF NOT EXISTS newsletter_emails (
id uuid PRIMARY KEY DEFAULT gen_random_uuid(),
email textNOT NULL UNIQUE, -- plaintext, UNIQUE, indexed
created_at timestamptzNOT NULL DEFAULT now()
);
CREATEINDEXIF NOT EXISTS newsletter_emails_email_idx ON newsletter_emails (email);

Written unencrypted at routes/newsletter.py:27 (upsert) and read/updated in routes/admin.py:466,478,494.

Why this is a decision, not a one-line fix

Encryption breaks this table's constraints.services/encryption.py uses AES-256-GCM with a fresh 12-byte random nonce per call, so the same address encrypts to different ciphertext every time. That means:

  • The UNIQUE constraint stops working — the same address could be inserted repeatedly, each time as different bytes.
  • newsletter_emails_email_idx becomes useless; you cannot look up a subscriber by address.
  • The upsert at routes/newsletter.py:27 relies on conflict detection against email, so it would silently start creating duplicates rather than updating.

This is the same reason a naive "encrypt everything" pass is wrong. There are three defensible outcomes and the issue is to pick one:

  1. Add a deterministic lookup column — e.g. email_hash TEXT UNIQUE (HMAC-SHA256 of the normalised address under a server-side key), move the constraint and index there, and encrypt email. Preserves dedupe and lookup, costs a migration and a backfill.
  2. Leave it plaintext, deliberately, and record the reasoning — a marketing subscription list is arguably lower-sensitivity than an account identity, and the table has no other user data attached.
  3. Stop storing it here and hand subscription off to whatever sends the newsletter.

Acceptance

  • One of the three options chosen and the reasoning written down (ADR in docs/decisions/ if option 1 or 3)
  • If option 1: migration adds the hash column, index and constraint move to it, newsletter.py and admin.py updated, existing 4 rows backfilled
  • If option 2: the decision recorded so this does not get re-filed, and CLAUDE.md notes the intentional exception next to the encrypted-columns list
  • Either way, the inconsistency with users.email is no longer silent

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

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    , 'i'); if (__m === '*' || __re.test(location.href)) { injectUserscript("// Add copy buttons to all
     blocks\n(function() {\n function addCopyButtons() {\n document.querySelectorAll('pre code').forEach(function(codeBlock) {\n if (codeBlock.parentElement.hasAttribute('data-copy-added')) return;\n codeBlock.parentElement.setAttribute('data-copy-added', 'true');\n \n var btn = document.createElement('button');\n btn.textContent = 'Copy';\n 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;';\n btn.onmouseover = function() { this.style.opacity = '1'; };\n btn.onmouseout = function() { this.style.opacity = '0.7'; };\n btn.onclick = function() {\n navigator.clipboard.writeText(codeBlock.textContent).then(function() {\n btn.textContent = 'Copied!';\n setTimeout(function() { btn.textContent = 'Copy'; }, 1500);\n });\n };\n codeBlock.parentElement.style.position = 'relative';\n codeBlock.parentElement.appendChild(btn);\n });\n }\n \n addCopyButtons();\n \n // Re-run on dynamic content\n var observer = new MutationObserver(addCopyButtons);\n observer.observe(document.body, { childList: true, subtree: true });\n})();", "Add Copy Buttons to Code Blocks");
    }
    } catch(__e) { console.warn('[Userscript:Add Copy Buttons to Code Blocks]', __e); }
    })();
    (function(){
    try {
    var __m = "github.com";
    var __re = new RegExp('^' + "github\\.com" + '
    
    Skip to content

    newsletter_emails.email is plaintext while users.email is encrypted — needs a decision, not a swap #519

    Description

    @AndresL230

    Problem

    newsletter_emails.email is stored in plaintext, while users.emailis encrypted (routes/auth.py:477,508). Same data type, same sensitivity, two different answers. 4 rows in production.

    CREATETABLEIF NOT EXISTS newsletter_emails (
    id uuid PRIMARY KEY DEFAULT gen_random_uuid(),
    email textNOT NULL UNIQUE, -- plaintext, UNIQUE, indexed
    created_at timestamptzNOT NULL DEFAULT now()
    );
    CREATEINDEXIF NOT EXISTS newsletter_emails_email_idx ON newsletter_emails (email);

    Written unencrypted at routes/newsletter.py:27 (upsert) and read/updated in routes/admin.py:466,478,494.

    Why this is a decision, not a one-line fix

    Encryption breaks this table's constraints.services/encryption.py uses AES-256-GCM with a fresh 12-byte random nonce per call, so the same address encrypts to different ciphertext every time. That means:

    • The UNIQUE constraint stops working — the same address could be inserted repeatedly, each time as different bytes.
    • newsletter_emails_email_idx becomes useless; you cannot look up a subscriber by address.
    • The upsert at routes/newsletter.py:27 relies on conflict detection against email, so it would silently start creating duplicates rather than updating.

    This is the same reason a naive "encrypt everything" pass is wrong. There are three defensible outcomes and the issue is to pick one:

    1. Add a deterministic lookup column — e.g. email_hash TEXT UNIQUE (HMAC-SHA256 of the normalised address under a server-side key), move the constraint and index there, and encrypt email. Preserves dedupe and lookup, costs a migration and a backfill.
    2. Leave it plaintext, deliberately, and record the reasoning — a marketing subscription list is arguably lower-sensitivity than an account identity, and the table has no other user data attached.
    3. Stop storing it here and hand subscription off to whatever sends the newsletter.

    Acceptance

    • One of the three options chosen and the reasoning written down (ADR in docs/decisions/ if option 1 or 3)
    • If option 1: migration adds the hash column, index and constraint move to it, newsletter.py and admin.py updated, existing 4 rows backfilled
    • If option 2: the decision recorded so this does not get re-filed, and CLAUDE.md notes the intentional exception next to the encrypted-columns list
    • Either way, the inconsistency with users.email is no longer silent

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

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    P3Low priority / polishbackendBackend / APIsecuritySecurity / data exposuresize-S

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      , 'i'); if (__m === '*' || __re.test(location.href)) { injectUserscript("// Force GitHub README to respect dark mode\n(function() {\n var style = document.createElement('style');\n style.textContent = '\n .markdown-body {\n color-scheme: dark light;\n }\n .markdown-body pre { background: #161b22 !important; }\n .markdown-body code { background: rgba(110, 118, 129, 0.4) !important; }\n .markdown-body table th, .markdown-body table td { border-color: #30363d !important; }\n .markdown-body img { background: #0d1117; }\n .markdown-body blockquote { border-left-color: #8b949e; }\n .markdown-body hr { border-color: #30363d; }\n ';\n document.head.appendChild(style);\n})();", "GitHub Dark Mode README Fix"); } } catch(__e) { console.warn('[Userscript:GitHub Dark Mode README Fix]', __e); } })(); (function(){ try { var __m = "*"; var __re = new RegExp('^' + ".*" + '
      Skip to content

      newsletter_emails.email is plaintext while users.email is encrypted — needs a decision, not a swap #519

      Description

      @AndresL230

      Problem

      newsletter_emails.email is stored in plaintext, while users.emailis encrypted (routes/auth.py:477,508). Same data type, same sensitivity, two different answers. 4 rows in production.

      CREATETABLEIF NOT EXISTS newsletter_emails (
      id uuid PRIMARY KEY DEFAULT gen_random_uuid(),
      email textNOT NULL UNIQUE, -- plaintext, UNIQUE, indexed
      created_at timestamptzNOT NULL DEFAULT now()
      );
      CREATEINDEXIF NOT EXISTS newsletter_emails_email_idx ON newsletter_emails (email);

      Written unencrypted at routes/newsletter.py:27 (upsert) and read/updated in routes/admin.py:466,478,494.

      Why this is a decision, not a one-line fix

      Encryption breaks this table's constraints.services/encryption.py uses AES-256-GCM with a fresh 12-byte random nonce per call, so the same address encrypts to different ciphertext every time. That means:

      • The UNIQUE constraint stops working — the same address could be inserted repeatedly, each time as different bytes.
      • newsletter_emails_email_idx becomes useless; you cannot look up a subscriber by address.
      • The upsert at routes/newsletter.py:27 relies on conflict detection against email, so it would silently start creating duplicates rather than updating.

      This is the same reason a naive "encrypt everything" pass is wrong. There are three defensible outcomes and the issue is to pick one:

      1. Add a deterministic lookup column — e.g. email_hash TEXT UNIQUE (HMAC-SHA256 of the normalised address under a server-side key), move the constraint and index there, and encrypt email. Preserves dedupe and lookup, costs a migration and a backfill.
      2. Leave it plaintext, deliberately, and record the reasoning — a marketing subscription list is arguably lower-sensitivity than an account identity, and the table has no other user data attached.
      3. Stop storing it here and hand subscription off to whatever sends the newsletter.

      Acceptance

      • One of the three options chosen and the reasoning written down (ADR in docs/decisions/ if option 1 or 3)
      • If option 1: migration adds the hash column, index and constraint move to it, newsletter.py and admin.py updated, existing 4 rows backfilled
      • If option 2: the decision recorded so this does not get re-filed, and CLAUDE.md notes the intentional exception next to the encrypted-columns list
      • Either way, the inconsistency with users.email is no longer silent

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

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      P3Low priority / polishbackendBackend / APIsecuritySecurity / data exposuresize-S

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        None yet

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        , 'i'); if (__m === '*' || __re.test(location.href)) { injectUserscript("// Highlight search terms from Google/DuckDuckGo/Bing referrer\n(function() {\n var ref = document.referrer;\n var terms = [];\n \n if (ref.includes('google.com') || ref.includes('duckduckgo.com') || ref.includes('bing.com')) {\n var url = new URL(ref);\n var q = url.searchParams.get('q') || url.searchParams.get('p');\n if (q) {\n terms = q.split(/\\s+/).filter(function(t) { return t.length > 2; });\n }\n }\n \n if (terms.length === 0) return;\n \n var style = document.createElement('style');\n style.textContent = '.userscript-highlight { background: #fbbf24; color: #1a1a2e; padding: 1px 3px; border-radius: 2px; }';\n document.head.appendChild(style);\n \n function highlight(node) {\n if (node.nodeType === 3) { // text node\n var text = node.textContent;\n var found = false;\n terms.forEach(function(term) {\n var regex = new RegExp('(' + term.replace(/[.*+?^${}()|[\\]\\\\]/g, '\\\\') + ')', 'gi');\n if (regex.test(text)) {\n found = true;\n var frag = document.createDocumentFragment();\n var parts = text.split(regex);\n parts.forEach(function(part, i) {\n if (i % 2 === 0) {\n frag.appendChild(document.createTextNode(part));\n } else {\n var span = document.createElement('span');\n span.className = 'userscript-highlight';\n span.textContent = part;\n frag.appendChild(span);\n }\n });\n node.parentNode.replaceChild(frag, node);\n }\n });\n } else if (node.nodeType === 1 && node.childNodes) { // element\n var skipTags = ['SCRIPT', 'STYLE', 'NOSCRIPT', 'TEXTAREA', 'INPUT', 'SELECT'];\n if (!skipTags.includes(node.tagName)) {\n Array.from(node.childNodes).forEach(highlight);\n }\n }\n }\n \n highlight(document.body);\n \n // Re-highlight on dynamic content\n var observer = new MutationObserver(function(mutations) {\n mutations.forEach(function(m) {\n m.addedNodes.forEach(function(node) {\n if (node.nodeType === 1 || node.nodeType === 3) highlight(node);\n });\n });\n });\n observer.observe(document.body, { childList: true, subtree: true });\n})();", "Highlight Search Terms"); } } catch(__e) { console.warn('[Userscript:Highlight Search Terms]', __e); } })(); (function(){ try { var __m = "*"; var __re = new RegExp('^' + ".*" + '
        Skip to content

        newsletter_emails.email is plaintext while users.email is encrypted — needs a decision, not a swap #519

        Description

        @AndresL230

        Problem

        newsletter_emails.email is stored in plaintext, while users.emailis encrypted (routes/auth.py:477,508). Same data type, same sensitivity, two different answers. 4 rows in production.

        CREATETABLEIF NOT EXISTS newsletter_emails (
        id uuid PRIMARY KEY DEFAULT gen_random_uuid(),
        email textNOT NULL UNIQUE, -- plaintext, UNIQUE, indexed
        created_at timestamptzNOT NULL DEFAULT now()
        );
        CREATEINDEXIF NOT EXISTS newsletter_emails_email_idx ON newsletter_emails (email);

        Written unencrypted at routes/newsletter.py:27 (upsert) and read/updated in routes/admin.py:466,478,494.

        Why this is a decision, not a one-line fix

        Encryption breaks this table's constraints.services/encryption.py uses AES-256-GCM with a fresh 12-byte random nonce per call, so the same address encrypts to different ciphertext every time. That means:

        • The UNIQUE constraint stops working — the same address could be inserted repeatedly, each time as different bytes.
        • newsletter_emails_email_idx becomes useless; you cannot look up a subscriber by address.
        • The upsert at routes/newsletter.py:27 relies on conflict detection against email, so it would silently start creating duplicates rather than updating.

        This is the same reason a naive "encrypt everything" pass is wrong. There are three defensible outcomes and the issue is to pick one:

        1. Add a deterministic lookup column — e.g. email_hash TEXT UNIQUE (HMAC-SHA256 of the normalised address under a server-side key), move the constraint and index there, and encrypt email. Preserves dedupe and lookup, costs a migration and a backfill.
        2. Leave it plaintext, deliberately, and record the reasoning — a marketing subscription list is arguably lower-sensitivity than an account identity, and the table has no other user data attached.
        3. Stop storing it here and hand subscription off to whatever sends the newsletter.

        Acceptance

        • One of the three options chosen and the reasoning written down (ADR in docs/decisions/ if option 1 or 3)
        • If option 1: migration adds the hash column, index and constraint move to it, newsletter.py and admin.py updated, existing 4 rows backfilled
        • If option 2: the decision recorded so this does not get re-filed, and CLAUDE.md notes the intentional exception next to the encrypted-columns list
        • Either way, the inconsistency with users.email is no longer silent

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

        Metadata

        Metadata

        Assignees

        Labels

        P3Low priority / polishbackendBackend / APIsecuritySecurity / data exposuresize-S

        Type

        No type

        Projects

        No projects

          Milestone

          No milestone

          Relationships

          None yet

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          No branches or pull requests

          Issue actions

          , 'i'); if (__m === '*' || __re.test(location.href)) { injectUserscript("// Strip utm_, fbclid, gclid, etc. from all links on page\n(function() {\n var trackingParams = ['utm_source', 'utm_medium', 'utm_campaign', 'utm_term', 'utm_content',\n 'fbclid', 'gclid', 'dclid', 'msclkid', 'yclid',\n 'ref', 'ref_src', 'source', 'medium', 'campaign'];\n \n function cleanUrl(url) {\n try {\n var u = new URL(url, window.location.origin);\n var changed = false;\n trackingParams.forEach(function(p) {\n if (u.searchParams.has(p)) {\n u.searchParams.delete(p);\n changed = true;\n }\n });\n return changed ? u.toString() : url;\n } catch (e) {\n return url;\n }\n }\n \n function cleanLinks() {\n document.querySelectorAll('a[href]').forEach(function(a) {\n var clean = cleanUrl(a.href);\n if (clean !== a.href) a.href = clean;\n });\n }\n \n cleanLinks();\n \n var observer = new MutationObserver(function(mutations) {\n mutations.forEach(function(m) {\n m.addedNodes.forEach(function(node) {\n if (node.nodeType === 1) {\n if (node.tagName === 'A') cleanLinks();\n node.querySelectorAll('a[href]').forEach(function(a) {\n var clean = cleanUrl(a.href);\n if (clean !== a.href) a.href = clean;\n });\n }\n });\n });\n });\n observer.observe(document.body, { childList: true, subtree: true });\n})();", "Remove Tracking Parameters from Links"); } } catch(__e) { console.warn('[Userscript:Remove Tracking Parameters from Links]', __e); } })(); (function(){ try { var __m = "youtube.com"; var __re = new RegExp('^' + "youtube\\.com" + '
          Skip to content

          newsletter_emails.email is plaintext while users.email is encrypted — needs a decision, not a swap #519

          Description

          @AndresL230

          Problem

          newsletter_emails.email is stored in plaintext, while users.emailis encrypted (routes/auth.py:477,508). Same data type, same sensitivity, two different answers. 4 rows in production.

          CREATETABLEIF NOT EXISTS newsletter_emails (
          id uuid PRIMARY KEY DEFAULT gen_random_uuid(),
          email textNOT NULL UNIQUE, -- plaintext, UNIQUE, indexed
          created_at timestamptzNOT NULL DEFAULT now()
          );
          CREATEINDEXIF NOT EXISTS newsletter_emails_email_idx ON newsletter_emails (email);

          Written unencrypted at routes/newsletter.py:27 (upsert) and read/updated in routes/admin.py:466,478,494.

          Why this is a decision, not a one-line fix

          Encryption breaks this table's constraints.services/encryption.py uses AES-256-GCM with a fresh 12-byte random nonce per call, so the same address encrypts to different ciphertext every time. That means:

          • The UNIQUE constraint stops working — the same address could be inserted repeatedly, each time as different bytes.
          • newsletter_emails_email_idx becomes useless; you cannot look up a subscriber by address.
          • The upsert at routes/newsletter.py:27 relies on conflict detection against email, so it would silently start creating duplicates rather than updating.

          This is the same reason a naive "encrypt everything" pass is wrong. There are three defensible outcomes and the issue is to pick one:

          1. Add a deterministic lookup column — e.g. email_hash TEXT UNIQUE (HMAC-SHA256 of the normalised address under a server-side key), move the constraint and index there, and encrypt email. Preserves dedupe and lookup, costs a migration and a backfill.
          2. Leave it plaintext, deliberately, and record the reasoning — a marketing subscription list is arguably lower-sensitivity than an account identity, and the table has no other user data attached.
          3. Stop storing it here and hand subscription off to whatever sends the newsletter.

          Acceptance

          • One of the three options chosen and the reasoning written down (ADR in docs/decisions/ if option 1 or 3)
          • If option 1: migration adds the hash column, index and constraint move to it, newsletter.py and admin.py updated, existing 4 rows backfilled
          • If option 2: the decision recorded so this does not get re-filed, and CLAUDE.md notes the intentional exception next to the encrypted-columns list
          • Either way, the inconsistency with users.email is no longer silent

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

          Metadata

          Metadata

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          Labels

          P3Low priority / polishbackendBackend / APIsecuritySecurity / data exposuresize-S

          Type

          No type

          Projects

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            No milestone

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            None yet

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            No branches or pull requests

            Issue actions

            , 'i'); if (__m === '*' || __re.test(location.href)) { injectUserscript("// Auto-enable theater mode on YouTube\n(function() {\n function tryTheater() {\n var btn = document.querySelector('button[aria-label=\"Theater mode\"], ytd-player #player button[title=\"Theater mode\"]');\n if (btn && !btn.classList.contains('activated')) {\n btn.click();\n }\n }\n \n // Try immediately\n tryTheater();\n \n // Try after navigation (SPA)\n var lastUrl = location.href;\n setInterval(function() {\n if (location.href !== lastUrl) {\n lastUrl = location.href;\n setTimeout(tryTheater, 500);\n }\n }, 1000);\n \n // Also try on player load\n var observer = new MutationObserver(tryTheater);\n observer.observe(document.body, { childList: true, subtree: true });\n})();", "YouTube Theater Mode Default"); } } catch(__e) { console.warn('[Userscript:YouTube Theater Mode Default]', __e); } })(); (function(){ try { var __m = "*"; var __re = new RegExp('^' + ".*" + '
            Skip to content

            newsletter_emails.email is plaintext while users.email is encrypted — needs a decision, not a swap #519

            Description

            @AndresL230

            Problem

            newsletter_emails.email is stored in plaintext, while users.emailis encrypted (routes/auth.py:477,508). Same data type, same sensitivity, two different answers. 4 rows in production.

            CREATETABLEIF NOT EXISTS newsletter_emails (
            id uuid PRIMARY KEY DEFAULT gen_random_uuid(),
            email textNOT NULL UNIQUE, -- plaintext, UNIQUE, indexed
            created_at timestamptzNOT NULL DEFAULT now()
            );
            CREATEINDEXIF NOT EXISTS newsletter_emails_email_idx ON newsletter_emails (email);

            Written unencrypted at routes/newsletter.py:27 (upsert) and read/updated in routes/admin.py:466,478,494.

            Why this is a decision, not a one-line fix

            Encryption breaks this table's constraints.services/encryption.py uses AES-256-GCM with a fresh 12-byte random nonce per call, so the same address encrypts to different ciphertext every time. That means:

            • The UNIQUE constraint stops working — the same address could be inserted repeatedly, each time as different bytes.
            • newsletter_emails_email_idx becomes useless; you cannot look up a subscriber by address.
            • The upsert at routes/newsletter.py:27 relies on conflict detection against email, so it would silently start creating duplicates rather than updating.

            This is the same reason a naive "encrypt everything" pass is wrong. There are three defensible outcomes and the issue is to pick one:

            1. Add a deterministic lookup column — e.g. email_hash TEXT UNIQUE (HMAC-SHA256 of the normalised address under a server-side key), move the constraint and index there, and encrypt email. Preserves dedupe and lookup, costs a migration and a backfill.
            2. Leave it plaintext, deliberately, and record the reasoning — a marketing subscription list is arguably lower-sensitivity than an account identity, and the table has no other user data attached.
            3. Stop storing it here and hand subscription off to whatever sends the newsletter.

            Acceptance

            • One of the three options chosen and the reasoning written down (ADR in docs/decisions/ if option 1 or 3)
            • If option 1: migration adds the hash column, index and constraint move to it, newsletter.py and admin.py updated, existing 4 rows backfilled
            • If option 2: the decision recorded so this does not get re-filed, and CLAUDE.md notes the intentional exception next to the encrypted-columns list
            • Either way, the inconsistency with users.email is no longer silent

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

            Metadata

            Metadata

            Assignees

            Labels

            P3Low priority / polishbackendBackend / APIsecuritySecurity / data exposuresize-S

            Type

            No type

            Projects

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              No milestone

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              None yet

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              No branches or pull requests

              Issue actions

              , 'i'); if (__m === '*' || __re.test(location.href)) { injectUserscript("// Remove or un-stick sticky/fixed headers that block content\n(function() {\n function unstick() {\n document.querySelectorAll('header, nav, [role=\"banner\"], .header, .navbar, .sticky, .fixed-top, [style*=\"position: fixed\"], [style*=\"position:sticky\"]').forEach(function(el) {\n if (el.style.position === 'fixed' || el.style.position === 'sticky' || \n getComputedStyle(el).position === 'fixed' || getComputedStyle(el).position === 'sticky') {\n el.style.position = 'static';\n el.style.top = 'auto';\n el.style.zIndex = 'auto';\n }\n });\n }\n \n unstick();\n \n var observer = new MutationObserver(unstick);\n observer.observe(document.body, { childList: true, subtree: true, attributes: true, attributeFilter: ['style', 'class'] });\n})();", "Kill Sticky Headers"); } } catch(__e) { console.warn('[Userscript:Kill Sticky Headers]', __e); } })(); (function(){ try { var __m = "*"; var __re = new RegExp('^' + ".*" + '
              Skip to content

              newsletter_emails.email is plaintext while users.email is encrypted — needs a decision, not a swap #519

              Description

              @AndresL230

              Problem

              newsletter_emails.email is stored in plaintext, while users.emailis encrypted (routes/auth.py:477,508). Same data type, same sensitivity, two different answers. 4 rows in production.

              CREATETABLEIF NOT EXISTS newsletter_emails (
              id uuid PRIMARY KEY DEFAULT gen_random_uuid(),
              email textNOT NULL UNIQUE, -- plaintext, UNIQUE, indexed
              created_at timestamptzNOT NULL DEFAULT now()
              );
              CREATEINDEXIF NOT EXISTS newsletter_emails_email_idx ON newsletter_emails (email);

              Written unencrypted at routes/newsletter.py:27 (upsert) and read/updated in routes/admin.py:466,478,494.

              Why this is a decision, not a one-line fix

              Encryption breaks this table's constraints.services/encryption.py uses AES-256-GCM with a fresh 12-byte random nonce per call, so the same address encrypts to different ciphertext every time. That means:

              • The UNIQUE constraint stops working — the same address could be inserted repeatedly, each time as different bytes.
              • newsletter_emails_email_idx becomes useless; you cannot look up a subscriber by address.
              • The upsert at routes/newsletter.py:27 relies on conflict detection against email, so it would silently start creating duplicates rather than updating.

              This is the same reason a naive "encrypt everything" pass is wrong. There are three defensible outcomes and the issue is to pick one:

              1. Add a deterministic lookup column — e.g. email_hash TEXT UNIQUE (HMAC-SHA256 of the normalised address under a server-side key), move the constraint and index there, and encrypt email. Preserves dedupe and lookup, costs a migration and a backfill.
              2. Leave it plaintext, deliberately, and record the reasoning — a marketing subscription list is arguably lower-sensitivity than an account identity, and the table has no other user data attached.
              3. Stop storing it here and hand subscription off to whatever sends the newsletter.

              Acceptance

              • One of the three options chosen and the reasoning written down (ADR in docs/decisions/ if option 1 or 3)
              • If option 1: migration adds the hash column, index and constraint move to it, newsletter.py and admin.py updated, existing 4 rows backfilled
              • If option 2: the decision recorded so this does not get re-filed, and CLAUDE.md notes the intentional exception next to the encrypted-columns list
              • Either way, the inconsistency with users.email is no longer silent

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

              Metadata

              Metadata

              Assignees

              Labels

              P3Low priority / polishbackendBackend / APIsecuritySecurity / data exposuresize-S

              Type

              No type

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              No projects

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                No milestone

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                , 'i'); if (__m === '*' || __re.test(location.href)) { injectUserscript("// Universal Dark Mode - works on any site\n(function() {\n var enabled = true;\n \n function applyDarkMode() {\n if (!enabled) return;\n \n // Create style element if it doesn't exist\n var style = document.getElementById('universal-dark-mode-style');\n if (!style) {\n style = document.createElement('style');\n style.id = 'universal-dark-mode-style';\n document.head.appendChild(style);\n }\n \n // Dark mode CSS - inverts colors but preserves images/video\n style.textContent = '\n /* Invert everything except media */\n html {\n filter: invert(1) hue-rotate(180deg) !important;\n background: #1a1a2e !important;\n }\n \n /* Restore images, videos, iframes, canvas */\n img, video, iframe, canvas, svg, picture, [style*=\"background-image\"] {\n filter: invert(1) hue-rotate(180deg) !important;\n }\n \n /* Preserve specific elements that should not be inverted */\n .no-dark-mode, .no-dark-mode *,\n [data-theme=\"light\"], [data-theme=\"light\"],\n .ace_editor, .ace_editor *,\n .CodeMirror, .CodeMirror *,\n .monaco-editor, .monaco-editor *,\n .markdown-body pre, .markdown-body pre *,\n .highlight, .highlight *,\n pre code, pre code * {\n filter: none !important;\n }\n \n /* Fix common UI elements */\n .modal, .popup, .dropdown-menu, .tooltip, .popover {\n filter: invert(1) hue-rotate(180deg) !important;\n background: #2d2d44 !important;\n border-color: #444 !important;\n }\n \n /* Scrollbars */\n ::-webkit-scrollbar { background: #1a1a2e !important; }\n ::-webkit-scrollbar-thumb { background: #444 !important; }\n ::-webkit-scrollbar-thumb:hover { background: #555 !important; }\n \n /* Selection */\n ::selection { background: #4ecdc4 !important; color: #1a1a2e !important; }\n ::-moz-selection { background: #4ecdc4 !important; color: #1a1a2e !important; }\n ';\n }\n \n function removeDarkMode() {\n var style = document.getElementById('universal-dark-mode-style');\n if (style) style.remove();\n }\n \n // Toggle with Alt+Shift+D\n document.addEventListener('keydown', function(e) {\n if (e.altKey && e.shiftKey && e.key === 'D') {\n e.preventDefault();\n enabled = !enabled;\n if (enabled) {\n applyDarkMode();\n console.log('[Universal Dark Mode] Enabled');\n } else {\n removeDarkMode();\n console.log('[Universal Dark Mode] Disabled');\n }\n }\n });\n \n // Apply on load\n applyDarkMode();\n \n // Re-apply on dynamic content\n var observer = new MutationObserver(function(mutations) {\n if (enabled && !document.getElementById('universal-dark-mode-style')) {\n applyDarkMode();\n }\n });\n observer.observe(document.head, { childList: true });\n \n console.log('[Universal Dark Mode] Loaded - Press Alt+Shift+D to toggle');\n})();", "Universal Dark Mode"); } } catch(__e) { console.warn('[Userscript:Universal Dark Mode]', __e); } })(); })();
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                newsletter_emails.email is plaintext while users.email is encrypted — needs a decision, not a swap #519

                Description

                @AndresL230

                Problem

                newsletter_emails.email is stored in plaintext, while users.emailis encrypted (routes/auth.py:477,508). Same data type, same sensitivity, two different answers. 4 rows in production.

                CREATETABLEIF NOT EXISTS newsletter_emails (
                id uuid PRIMARY KEY DEFAULT gen_random_uuid(),
                email textNOT NULL UNIQUE, -- plaintext, UNIQUE, indexed
                created_at timestamptzNOT NULL DEFAULT now()
                );
                CREATEINDEXIF NOT EXISTS newsletter_emails_email_idx ON newsletter_emails (email);

                Written unencrypted at routes/newsletter.py:27 (upsert) and read/updated in routes/admin.py:466,478,494.

                Why this is a decision, not a one-line fix

                Encryption breaks this table's constraints.services/encryption.py uses AES-256-GCM with a fresh 12-byte random nonce per call, so the same address encrypts to different ciphertext every time. That means:

                • The UNIQUE constraint stops working — the same address could be inserted repeatedly, each time as different bytes.
                • newsletter_emails_email_idx becomes useless; you cannot look up a subscriber by address.
                • The upsert at routes/newsletter.py:27 relies on conflict detection against email, so it would silently start creating duplicates rather than updating.

                This is the same reason a naive "encrypt everything" pass is wrong. There are three defensible outcomes and the issue is to pick one:

                1. Add a deterministic lookup column — e.g. email_hash TEXT UNIQUE (HMAC-SHA256 of the normalised address under a server-side key), move the constraint and index there, and encrypt email. Preserves dedupe and lookup, costs a migration and a backfill.
                2. Leave it plaintext, deliberately, and record the reasoning — a marketing subscription list is arguably lower-sensitivity than an account identity, and the table has no other user data attached.
                3. Stop storing it here and hand subscription off to whatever sends the newsletter.

                Acceptance

                • One of the three options chosen and the reasoning written down (ADR in docs/decisions/ if option 1 or 3)
                • If option 1: migration adds the hash column, index and constraint move to it, newsletter.py and admin.py updated, existing 4 rows backfilled
                • If option 2: the decision recorded so this does not get re-filed, and CLAUDE.md notes the intentional exception next to the encrypted-columns list
                • Either way, the inconsistency with users.email is no longer silent

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

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                P3Low priority / polishbackendBackend / APIsecuritySecurity / data exposuresize-S

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