stuff

server.js

@@ -635,6 +635,8 @@ let studyUsers = []
 let studyUsersWritePromise = Promise.resolve()
 const studyNotesCache = new Map() // userId -> { [sectionId]: string }
 const studyNotesWriteQueues = new Map() // userId -> Promise
+let studyReminders = { users: {}, updatedAt: new Date().toISOString() }
+let studyRemindersWritePromise = Promise.resolve()
 const studyProgressCache = new Map() // userId -> { byStudy: Record<string, { completedSectionIds: string[] }> }
 const studyProgressWriteQueues = new Map() // userId -> Promise
 let studyCommunityPosts = []
@@ -2244,6 +2246,28 @@ function normalizeStudyUsername(value) {
   return value.trim().toLowerCase()
 }
 
+function getStudyAvatarUrl(subject) {
+  let customAvatar = ''
+  let username = ''
+
+  if (subject && typeof subject === 'object') {
+    customAvatar = typeof subject.avatarUrl === 'string' ? subject.avatarUrl.trim() : ''
+    username = normalizeStudyUsername(subject.username)
+  } else if (typeof subject === 'string') {
+    username = normalizeStudyUsername(subject)
+  }
+
+  if (customAvatar) return customAvatar
+  if (!username) return ''
+  const hash = createHash('md5').update(username).digest('hex')
+  return `https://www.gravatar.com/avatar/${hash}?d=identicon&s=96`
+}
+
+function findStudyUserById(userId) {
+  if (typeof userId !== 'string' || !userId.trim()) return undefined
+  return studyUsers.find(user => user.id === userId)
+}
+
 function normalizeStudySlug(value) {
   if (typeof value !== 'string') return ''
   const trimmed = value.trim().toLowerCase()
@@ -2437,6 +2461,7 @@ function sanitizeStudyUsers(value) {
       : []
     const displayName = typeof item?.displayName === 'string' ? item.displayName.trim().slice(0, 80) : ''
     const subscribeNewsletter = item?.subscribeNewsletter !== false
+    const studyRemindersEnabled = item?.studyRemindersEnabled === true
     const pendingEmailChange = item?.pendingEmailChange && typeof item.pendingEmailChange === 'object' && !Array.isArray(item.pendingEmailChange)
       ? {
         newEmail: isValidStudyUsername(normalizeStudyUsername(item.pendingEmailChange.newEmail))
@@ -2454,13 +2479,11 @@ function sanitizeStudyUsers(value) {
       passwordHash,
       displayName,
       subscribeNewsletter,
-      pendingEmailChange: pendingEmailChange?.newEmail && pendingEmailChange?.tokenHash && pendingEmailChange.expiresAt > Date.now()
-        ? pendingEmailChange
-        : null,
+      studyRemindersEnabled,
       enrolledStudySlugs,
-      createdAt: typeof item?.createdAt === 'string' ? item.createdAt : new Date().toISOString(),
-      updatedAt: typeof item?.updatedAt === 'string' ? item.updatedAt : new Date().toISOString(),
+      avatarUrl: typeof item?.avatarUrl === 'string' ? item.avatarUrl.trim() : '',
       lastLoginAt: typeof item?.lastLoginAt === 'string' ? item.lastLoginAt : null,
+      pendingEmailChange,
     })
   }
 
@@ -2599,8 +2622,21 @@ function sanitizeStudyProgress(value) {
       const completedSectionIds = Array.isArray(studyData?.completedSectionIds)
         ? studyData.completedSectionIds.filter(id => typeof id === 'string' && id.trim()).map(id => id.trim())
         : []
+      const quizAnswers = studyData?.quizAnswers && typeof studyData?.quizAnswers === 'object' && !Array.isArray(studyData.quizAnswers)
+        ? Object.fromEntries(
+            Object.entries(studyData.quizAnswers)
+              .filter(([sectionId]) => typeof sectionId === 'string' && sectionId.trim())
+              .map(([sectionId, answers]) => [
+                sectionId.trim(),
+                Array.isArray(answers)
+                  ? answers.filter(answer => typeof answer === 'string').map(answer => answer.trim())
+                  : [],
+              ])
+          )
+        : {}
       progress.byStudy[studySlug.trim().toLowerCase()] = {
         completedSectionIds: Array.from(new Set(completedSectionIds)),
+        quizAnswers,
       }
     }
   }
@@ -2636,6 +2672,130 @@ function queueUserProgressWrite(userId) {
   studyProgressWriteQueues.set(userId, next)
 }
 
+function sanitizeStudyReminders(value) {
+  const defaultResult = { users: {}, updatedAt: new Date().toISOString() }
+  if (!value || typeof value !== 'object' || Array.isArray(value)) return defaultResult
+
+  const reminders = { users: {}, updatedAt: typeof value.updatedAt === 'string' ? value.updatedAt : new Date().toISOString() }
+  if (value.users && typeof value.users === 'object') {
+    for (const [userId, userData] of Object.entries(value.users)) {
+      if (typeof userId !== 'string' || !userId.trim()) continue
+      const studies = typeof userData === 'object' && userData && !Array.isArray(userData)
+        ? userData
+        : {}
+      const normalizedStudies = {}
+      for (const [studySlug, sectionIds] of Object.entries(studies)) {
+        if (typeof studySlug !== 'string' || !studySlug.trim()) continue
+        const ids = Array.isArray(sectionIds)
+          ? sectionIds.filter(id => typeof id === 'string' && id.trim()).map(id => id.trim())
+          : []
+        if (ids.length > 0) normalizedStudies[studySlug.trim().toLowerCase()] = Array.from(new Set(ids))
+      }
+      reminders.users[userId.trim()] = normalizedStudies
+    }
+  }
+
+  return reminders
+}
+
+async function loadStudyRemindersFromDisk() {
+  try {
+    const raw = await readFile(STUDY_REMINDERS_FILE, 'utf8')
+    studyReminders = sanitizeStudyReminders(JSON.parse(raw))
+  } catch {
+    studyReminders = { users: {}, updatedAt: new Date().toISOString() }
+  }
+}
+
+function queueStudyRemindersWrite() {
+  studyRemindersWritePromise = studyRemindersWritePromise
+    .then(async () => {
+      await mkdir(DATA_DIR, { recursive: true })
+      await writeFile(STUDY_REMINDERS_FILE, JSON.stringify(studyReminders, null, 2), 'utf8')
+    })
+    .catch(err => {
+      console.error('[study-reminders] failed to write reminders:', err)
+    })
+}
+
+async function sendStudyReminderEmail(email, displayName, studyTitle, sectionTitle, sectionReference, sectionUrl) {
+  if (!process.env.RESEND_API_KEY) return
+  try {
+    const resend = new Resend(process.env.RESEND_API_KEY)
+    const namePart = typeof displayName === 'string' && displayName.trim() ? displayName.trim() : 'friend'
+    const bodyHtml = (
+      `<p style="margin:0 0 16px;">Hi <strong style="color:#f0ead8;">${escapeHtml(namePart)}</strong>,</p>` +
+      `<p style="margin:0 0 16px;">A new study lesson is available in ${escapeHtml(studyTitle)}.</p>` +
+      `<p style="margin:0 0 16px;">${escapeHtml(sectionTitle)} (${escapeHtml(sectionReference)}) is now unlocked.</p>`
+    )
+    const footerHtml = `<p style="margin:0;font-family:Georgia,serif;font-size:12px;font-weight:300;color:#7a7060;line-height:1.6;">Grace and peace,<br/>Verse by Verse with Nate</p>`
+    const { error } = await resend.emails.send({
+      from: process.env.RESEND_FROM ?? 'Verse by Verse with Nate <hello@versebyversewithnate.us>',
+      to: [email],
+      subject: process.env.RESEND_REMINDER_SUBJECT ?? `New lesson available: ${sectionTitle}`,
+      text:
+        `Hi ${namePart},\n\n` +
+        `A new lesson is available in ${studyTitle}.\n` +
+        `${sectionTitle} (${sectionReference}) is now unlocked.\n\n` +
+        `Open it here: ${sectionUrl}\n\n` +
+        `Grace and peace,\nVerse by Verse with Nate`,
+      html: buildBrandedEmailHtml({
+        title: 'New Lesson Available',
+        eyebrow: 'Study Reminder',
+        bodyHtml,
+        ctaLabel: 'Open the Lesson',
+        ctaUrl: sectionUrl,
+        footerHtml,
+      }),
+    })
+    if (error) console.error('[study-reminder] send error:', error)
+  } catch (err) {
+    console.error('[study-reminder] send exception:', err)
+  }
+}
+
+async function scheduleStudyReminders() {
+  if (!cachedSiteContent) return
+  const now = new Date()
+  const userIds = studyUsers.filter(user => user.studyRemindersEnabled === true).map(user => user.id)
+  if (userIds.length === 0) return
+
+  for (const user of studyUsers) {
+    if (user.studyRemindersEnabled !== true) continue
+    const email = user.username
+    const displayName = user.displayName || email
+    const enrolledStudySlugs = Array.isArray(user.enrolledStudySlugs) ? user.enrolledStudySlugs : []
+    if (enrolledStudySlugs.length === 0) continue
+
+    const userSent = studyReminders.users[user.id] ?? {}
+    for (const studySlug of enrolledStudySlugs) {
+      const study = Array.isArray(cachedSiteContent.studies)
+        ? cachedSiteContent.studies.find(item => normalizeStudySlug(item?.slug) === studySlug)
+        : undefined
+      if (!study) continue
+
+      for (const section of study.sections ?? []) {
+        const sectionId = section.id
+        const releaseDate = getSectionReleaseDate(section)
+        if (!releaseDate) continue
+        if (releaseDate > now) continue
+        const sentForStudy = Array.isArray(userSent[studySlug]) ? userSent[studySlug] : []
+        if (sentForStudy.includes(sectionId)) continue
+
+        const hoursSinceRelease = (now.getTime() - releaseDate.getTime()) / (1000 * 60 * 60)
+        if (hoursSinceRelease > 24) continue
+
+        const sectionUrl = buildAbsoluteUrl(getCanonicalBaseUrl(), `/study/${study.slug}/${section.id}`)
+        await sendStudyReminderEmail(email, displayName, study.title, section.title, section.reference, sectionUrl)
+        userSent[studySlug] = [...sentForStudy, sectionId]
+        studyReminders.users[user.id] = userSent
+      }
+    }
+  }
+  studyReminders.updatedAt = new Date().toISOString()
+  queueStudyRemindersWrite()
+}
+
 async function migrateStudyNotesIfNeeded() {
   try {
     const raw = await readFile(STUDY_NOTES_FILE, 'utf8')
@@ -2779,6 +2939,8 @@ app.get('/api/study-auth/status', (req, res) => {
     username: user?.username ?? '',
     displayName: user?.displayName ?? '',
     subscribeNewsletter: user?.subscribeNewsletter !== false,
+    studyRemindersEnabled: user?.studyRemindersEnabled === true,
+    avatarUrl: user ? getStudyAvatarUrl(user) : '',
     enrolledStudySlugs: Array.isArray(user?.enrolledStudySlugs) ? user.enrolledStudySlugs : [],
   })
 })
@@ -2811,6 +2973,7 @@ app.post('/api/study-auth/signup', studyAuthRateLimiter, (req, res) => {
     passwordHash: hashStudyPassword(password),
     displayName,
     subscribeNewsletter: subscribe,
+    studyRemindersEnabled: false,
     pendingEmailChange: null,
     enrolledStudySlugs: [],
     createdAt: now,
@@ -2838,6 +3001,8 @@ app.post('/api/study-auth/signup', studyAuthRateLimiter, (req, res) => {
     username: user.username,
     displayName: user.displayName,
     subscribeNewsletter: user.subscribeNewsletter,
+    studyRemindersEnabled: user.studyRemindersEnabled === true,
+    avatarUrl: getStudyAvatarUrl(user.username),
     enrolledStudySlugs: user.enrolledStudySlugs,
   })
 })
@@ -2872,6 +3037,8 @@ app.post('/api/study-auth/login', studyAuthRateLimiter, (req, res) => {
     username: user.username,
     displayName: user.displayName ?? '',
     subscribeNewsletter: user.subscribeNewsletter !== false,
+    studyRemindersEnabled: user.studyRemindersEnabled === true,
+    avatarUrl: getStudyAvatarUrl(user.username),
     enrolledStudySlugs: user.enrolledStudySlugs ?? [],
   })
 })
@@ -3041,6 +3208,56 @@ app.post('/api/study-progress/:studySlug/:sectionId', requireStudyAuth, async (r
   res.json({ ok: true, studySlug, completedSectionIds: studyProgress.completedSectionIds })
 })
 
+app.get('/api/study-quiz/:studySlug/:sectionId', requireStudyAuth, async (req, res) => {
+  const user = req.studyUser
+  const studySlug = normalizeStudySlug(req.params.studySlug)
+  const sectionId = normalizeLessonSectionId(req.params.sectionId)
+  if (!studySlug || !sectionId) {
+    res.status(400).json({ message: 'Invalid study slug or section id.' })
+    return
+  }
+
+  if (!isStudyUserEnrolled(user, studySlug)) {
+    res.status(403).json({ message: 'Please enroll in this study to view quiz answers.' })
+    return
+  }
+
+  const progress = await loadUserProgress(user.id)
+  const quizAnswers = progress.byStudy[studySlug]?.quizAnswers?.[sectionId] ?? []
+  res.json({ studySlug, sectionId, answers: quizAnswers })
+})
+
+app.post('/api/study-quiz/:studySlug/:sectionId', requireStudyAuth, async (req, res) => {
+  const user = req.studyUser
+  const studySlug = normalizeStudySlug(req.params.studySlug)
+  const sectionId = normalizeLessonSectionId(req.params.sectionId)
+  if (!studySlug || !sectionId) {
+    res.status(400).json({ message: 'Invalid study slug or section id.' })
+    return
+  }
+
+  if (!isStudyUserEnrolled(user, studySlug)) {
+    res.status(403).json({ message: 'Please enroll in this study to save quiz answers.' })
+    return
+  }
+
+  const rawAnswers = req.body?.answers
+  const answers = Array.isArray(rawAnswers)
+    ? rawAnswers.map(answer => typeof answer === 'string' ? answer.trim() : '').filter(Boolean)
+    : []
+
+  const progress = await loadUserProgress(user.id)
+  const studyProgress = progress.byStudy[studySlug] ?? { completedSectionIds: [] }
+  studyProgress.quizAnswers = studyProgress.quizAnswers || {}
+  studyProgress.quizAnswers[sectionId] = answers
+  progress.byStudy[studySlug] = studyProgress
+  progress.updatedAt = new Date().toISOString()
+  studyProgressCache.set(user.id, progress)
+  queueUserProgressWrite(user.id)
+
+  res.json({ ok: true, studySlug, sectionId, answers })
+})
+
 app.delete('/api/study-progress/:studySlug/:sectionId', requireStudyAuth, async (req, res) => {
   const user = req.studyUser
   const studySlug = normalizeStudySlug(req.params.studySlug)
@@ -3084,6 +3301,23 @@ app.get('/api/study-community', requireStudyAuth, async (req, res) => {
     .filter(post => post.studySlug === studySlug)
     .sort((a, b) => new Date(b.createdAt).getTime() - new Date(a.createdAt).getTime())
     .slice(0, 50)
+    .map(post => {
+      const author = findStudyUserById(post.authorUserId)
+      const enrichedPost = {
+        ...post,
+        authorAvatarUrl: getStudyAvatarUrl(author || post.authorName || ''),
+        replies: Array.isArray(post.replies)
+          ? post.replies.map(reply => {
+            const replyAuthor = findStudyUserById(reply.authorUserId)
+            return {
+              ...reply,
+              authorAvatarUrl: getStudyAvatarUrl(replyAuthor || reply.authorName || ''),
+            }
+          })
+          : [],
+      }
+      return enrichedPost
+    })
 
   res.json({
     studySlug,
@@ -3115,6 +3349,7 @@ app.post('/api/study-community/posts', requireStudyAuth, async (req, res) => {
     sectionId,
     authorUserId: user.id,
     authorName,
+    authorAvatarUrl: getStudyAvatarUrl(user.username),
     message,
     createdAt: now,
     replies: [],
@@ -3152,6 +3387,7 @@ app.post('/api/study-community/posts/:postId/replies', requireStudyAuth, async (
     id: randomUUID(),
     authorUserId: user.id,
     authorName: user.displayName?.trim() || user.username,
+    authorAvatarUrl: getStudyAvatarUrl(user.username),
     message,
     createdAt: new Date().toISOString(),
   }
@@ -3167,86 +3403,151 @@ app.post('/api/study-community/posts/:postId/replies', requireStudyAuth, async (
 app.get('/api/study-account/export-notes', requireStudyAuth, async (req, res) => {
   const user = req.studyUser
   const notes = await loadUserNotes(user.id)
+  const progress = await loadUserProgress(user.id)
 
-  // Build a lookup of sectionId -> { title, reference, studyTitle } from cached content
+  // Build a lookup of sectionId -> { title, reference, studyTitle, description } from cached content
   const sectionMeta = {}
   const content = cachedSiteContent
-  if (content) {
-    const studies = Array.isArray(content.studies) && content.studies.length > 0
-      ? content.studies
-      : [{ slug: 'colossians', title: 'Colossians: Rooted in Christ', sections: content.colossiansStudySections ?? [] }]
-    for (const study of studies) {
-      for (const section of (study.sections ?? [])) {
-        sectionMeta[`${study.slug}--${section.id}`] = {
-          studyTitle: study.title,
-          title: section.title,
-          reference: section.reference,
-        }
+  const studies = content && Array.isArray(content.studies) && content.studies.length > 0
+    ? content.studies
+    : [{ slug: 'colossians', title: 'Colossians: Rooted in Christ', description: '', sections: content?.colossiansStudySections ?? [] }]
+
+  for (const study of studies) {
+    for (const section of (study.sections ?? [])) {
+      sectionMeta[`${study.slug}--${section.id}`] = {
+        studyTitle: study.title,
+        studyDescription: typeof study.description === 'string' ? study.description : '',
+        title: section.title,
+        reference: section.reference,
+        studyQuestions: Array.isArray(section.studyQuestions) ? section.studyQuestions : [],
       }
     }
   }
 
-  // Group notes by study
-  const byStudy = {}
+  const studyEntries = {}
+
   for (const [noteKey, noteText] of Object.entries(notes)) {
     if (!noteText?.trim()) continue
     const dashIndex = noteKey.indexOf('--')
     const studySlug = dashIndex >= 0 ? noteKey.slice(0, dashIndex) : 'unknown'
-    if (!byStudy[studySlug]) byStudy[studySlug] = []
-    byStudy[studySlug].push({ noteKey, noteText })
+    const sectionId = dashIndex >= 0 ? noteKey.slice(dashIndex + 2) : noteKey
+    if (!studyEntries[studySlug]) studyEntries[studySlug] = {}
+    studyEntries[studySlug][sectionId] = studyEntries[studySlug][sectionId] || {}
+    studyEntries[studySlug][sectionId].noteText = noteText.trim()
   }
 
+  for (const [studySlug, studyProgress] of Object.entries(progress.byStudy)) {
+    const quizAnswersBySection = studyProgress.quizAnswers || {}
+    for (const [sectionId, answers] of Object.entries(quizAnswersBySection)) {
+      if (!Array.isArray(answers) || answers.length === 0) continue
+      if (!studyEntries[studySlug]) studyEntries[studySlug] = {}
+      studyEntries[studySlug][sectionId] = studyEntries[studySlug][sectionId] || {}
+      studyEntries[studySlug][sectionId].quizAnswers = answers.filter(answer => typeof answer === 'string' && answer.trim()).map(answer => answer.trim())
+    }
+  }
+
+  const studySlugs = Array.from(new Set([
+    ...Object.keys(studyEntries),
+    ...Object.values(studies).map(study => study.slug),
+  ]))
+
   const docChildren = [
-    new Paragraph({
-      text: 'My Study Notes',
-      heading: HeadingLevel.TITLE,
-    }),
-    new Paragraph({
-      children: [new TextRun({ text: `Exported ${new Date().toLocaleDateString('en-US', { month: 'long', day: 'numeric', year: 'numeric' })}`, italics: true })],
-      spacing: { after: 400 },
-    }),
+    new Paragraph({ text: 'Verse by Verse with Nate', heading: HeadingLevel.TITLE }),
+    new Paragraph({ text: 'My Study Export', heading: HeadingLevel.HEADING_1, spacing: { after: 240 } }),
+    new Paragraph({ text: `Student: ${user.displayName || user.username}`, spacing: { after: 120 } }),
+    new Paragraph({ text: `Exported ${new Date().toLocaleDateString('en-US', { month: 'long', day: 'numeric', year: 'numeric' })}`, italics: true, spacing: { after: 400 } }),
   ]
 
-  for (const [studySlug, entries] of Object.entries(byStudy)) {
-    const studyTitle = entries[0] ? (sectionMeta[entries[0].noteKey]?.studyTitle ?? studySlug) : studySlug
+  for (const studySlug of studySlugs) {
+    const study = studies.find(item => normalizeStudySlug(item?.slug) === studySlug)
+    const studyTitle = study?.title || studySlug
+    const studyDescription = typeof study?.description === 'string' ? study.description : ''
+    const sectionIds = studyEntries[studySlug] ? Object.keys(studyEntries[studySlug]) : []
+
+    if (sectionIds.length === 0) continue
+
     docChildren.push(
       new Paragraph({ text: studyTitle, heading: HeadingLevel.HEADING_1, spacing: { before: 400 } }),
     )
-    for (const { noteKey, noteText } of entries) {
-      const meta = sectionMeta[noteKey]
-      const lessonTitle = meta?.title ?? noteKey
-      const reference = meta?.reference ?? ''
+    if (studyDescription) {
       docChildren.push(
-        new Paragraph({ text: lessonTitle, heading: HeadingLevel.HEADING_2, spacing: { before: 240 } }),
+        new Paragraph({ text: studyDescription, spacing: { after: 240 } }),
       )
-      if (reference) {
+    }
+    const noteCount = sectionIds.filter(sectionId => studyEntries[studySlug][sectionId].noteText).length
+    const quizCount = sectionIds.filter(sectionId => Array.isArray(studyEntries[studySlug][sectionId].quizAnswers) && studyEntries[studySlug][sectionId].quizAnswers.length > 0).length
+    docChildren.push(
+      new Paragraph({ text: `Notes: ${noteCount} | Quiz sections: ${quizCount}`, italics: true, spacing: { after: 240 } }),
+    )
+
+    const orderedSectionIds = study?.sections?.map(section => section.id).filter(id => sectionIds.includes(id)) ?? sectionIds
+    for (const sectionId of orderedSectionIds) {
+      const entry = studyEntries[studySlug][sectionId]
+      if (!entry) continue
+      const meta = sectionMeta[`${studySlug}--${sectionId}`] || { title: sectionId, reference: '' }
+      docChildren.push(
+        new Paragraph({ text: meta.title, heading: HeadingLevel.HEADING_2, spacing: { before: 240 } }),
+      )
+      if (meta.reference) {
         docChildren.push(
-          new Paragraph({
-            children: [new TextRun({ text: reference, italics: true, color: '555555' })],
-            spacing: { after: 120 },
-          }),
+          new Paragraph({ children: [new TextRun({ text: meta.reference, italics: true, color: '555555' })], spacing: { after: 120 } }),
         )
       }
-      for (const line of noteText.split('\n')) {
+      if (entry.noteText) {
         docChildren.push(
-          new Paragraph({ text: line.trim(), spacing: { after: 80 } }),
+          new Paragraph({ text: 'Notes', heading: HeadingLevel.HEADING_3, spacing: { before: 120 } }),
         )
+        for (const line of entry.noteText.split('\n')) {
+          docChildren.push(new Paragraph({ text: line.trim(), spacing: { after: 80 } }))
+        }
+      }
+      if (Array.isArray(meta.studyQuestions) && meta.studyQuestions.length > 0) {
+        docChildren.push(
+          new Paragraph({ text: 'Quiz Questions', heading: HeadingLevel.HEADING_3, spacing: { before: 160 } }),
+        )
+        meta.studyQuestions.forEach((question, index) => {
+          docChildren.push(
+            new Paragraph({
+              children: [
+                new TextRun({ text: `${index + 1}. `, bold: true }),
+                new TextRun({ text: question }),
+              ],
+              spacing: { after: 80 },
+            }),
+          )
+        })
+      }
+      if (Array.isArray(entry.quizAnswers) && entry.quizAnswers.length > 0) {
+        docChildren.push(
+          new Paragraph({ text: 'Quiz Answers', heading: HeadingLevel.HEADING_3, spacing: { before: 160 } }),
+        )
+        entry.quizAnswers.forEach((answer, index) => {
+          docChildren.push(
+            new Paragraph({
+              children: [
+                new TextRun({ text: `Answer ${index + 1}: `, bold: true }),
+                new TextRun({ text: answer }),
+              ],
+              spacing: { after: 80 },
+            }),
+          )
+        })
       }
     }
   }
 
-  if (docChildren.length <= 2) {
-    docChildren.push(new Paragraph({ text: 'No notes saved yet.', spacing: { before: 200 } }))
+  if (docChildren.length <= 4) {
+    docChildren.push(new Paragraph({ text: 'No notes or quiz answers saved yet.', spacing: { before: 200 } }))
   }
 
   const doc = new Document({
     creator: 'Verse by Verse with Nate',
-    title: 'My Study Notes',
+    title: 'My Study Export',
     sections: [{ children: docChildren }],
   })
 
   const buffer = await Packer.toBuffer(doc)
-  const filename = `my-study-notes-${new Date().toISOString().slice(0, 10)}.docx`
+  const filename = `my-study-export-${new Date().toISOString().slice(0, 10)}.docx`
   res.setHeader('Content-Disposition', `attachment; filename="${filename}"`)
   res.setHeader('Content-Type', 'application/vnd.openxmlformats-officedocument.wordprocessingml.document')
   res.send(buffer)
@@ -3304,6 +3605,8 @@ app.get('/api/study-account/overview', requireStudyAuth, async (req, res) => {
       username: user.username,
       displayName: user.displayName ?? '',
       subscribeNewsletter: user.subscribeNewsletter !== false,
+      studyRemindersEnabled: user.studyRemindersEnabled === true,
+      avatarUrl: getStudyAvatarUrl(user),
     },
     stats: {
       noteCount: Object.keys(notes).length,
@@ -3317,16 +3620,59 @@ app.get('/api/study-account/overview', requireStudyAuth, async (req, res) => {
 app.post('/api/study-account/profile', requireStudyAuth, (req, res) => {
   const user = req.studyUser
   const displayName = typeof req.body?.displayName === 'string' ? req.body.displayName.trim().slice(0, 80) : ''
+  const avatarUrl = typeof req.body?.avatarUrl === 'string' ? req.body.avatarUrl.trim() : ''
+  if (avatarUrl && !/^https?:\/\//i.test(avatarUrl) && !avatarUrl.startsWith('/uploads/') && !avatarUrl.startsWith('data:image/')) {
+    res.status(400).json({ message: 'Avatar must be a valid uploaded image, data URI, or https URL.' })
+    return
+  }
+
   user.displayName = displayName
+  user.avatarUrl = avatarUrl
   user.updatedAt = new Date().toISOString()
   queueStudyUsersWrite()
-  res.json({ ok: true, displayName: user.displayName })
+  res.json({ ok: true, displayName: user.displayName, avatarUrl: user.avatarUrl || getStudyAvatarUrl(user) })
+})
+
+app.post('/api/study-account/avatar-upload', requireStudyAuth, async (req, res) => {
+  try {
+    const filename = typeof req.body?.filename === 'string' ? req.body.filename : ''
+    const dataUrl = typeof req.body?.dataUrl === 'string' ? req.body.dataUrl : ''
+    const ext = inferImageExtensionFromDataUrl(dataUrl)
+
+    if (!ext) {
+      res.status(400).json({ message: 'Upload must be a PNG, JPG, WEBP, or GIF data URL.' })
+      return
+    }
+
+    const base64 = dataUrl.split(',')[1] ?? ''
+    const buffer = Buffer.from(base64, 'base64')
+    if (buffer.length === 0 || buffer.length > (4 * 1024 * 1024)) {
+      res.status(400).json({ message: 'Upload must be between 1 byte and 4MB.' })
+      return
+    }
+
+    const baseName = normalizeAssetBaseName(filename.replace(/\.[a-z0-9]+$/i, ''))
+    const finalName = `${baseName || 'avatar'}-${Date.now()}${ext}`
+
+    await mkdir(UPLOADS_DIR, { recursive: true })
+    await writeFile(path.join(UPLOADS_DIR, finalName), buffer)
+    const metadata = await readUploadsMetadata()
+    metadata[finalName] = []
+    await writeUploadsMetadata(metadata)
+
+    res.json({ ok: true, url: `/uploads/${finalName}` })
+  } catch (err) {
+    console.error('[study-account-avatar-upload] upload error:', err)
+    res.status(500).json({ message: 'Avatar upload failed.' })
+  }
 })
 
 app.patch('/api/study-account/preferences', requireStudyAuth, (req, res) => {
   const user = req.studyUser
   const subscribeNewsletter = req.body?.subscribeNewsletter === true
+  const studyRemindersEnabled = req.body?.studyRemindersEnabled === true
   user.subscribeNewsletter = subscribeNewsletter
+  user.studyRemindersEnabled = studyRemindersEnabled
   user.updatedAt = new Date().toISOString()
   queueStudyUsersWrite()
 
@@ -3334,7 +3680,7 @@ app.patch('/api/study-account/preferences', requireStudyAuth, (req, res) => {
     syncContactToResend(user.displayName || user.username, user.username).catch(err => console.error('[study-account] resend sync error:', err))
   }
 
-  res.json({ ok: true, subscribeNewsletter: user.subscribeNewsletter })
+  res.json({ ok: true, subscribeNewsletter: user.subscribeNewsletter, studyRemindersEnabled: user.studyRemindersEnabled === true })
 })
 
 app.post('/api/study-account/request-email-change', studyAuthRateLimiter, requireStudyAuth, async (req, res) => {
@@ -5150,6 +5496,7 @@ Promise.all([
   loadDraftQuestionsFromDisk(),
   loadStudyUsersFromDisk(),
   loadStudyCommunityFromDisk(),
+  loadStudyRemindersFromDisk(),
   migrateStudyNotesIfNeeded(),
   loadDownloadCountsFromDisk(),
   loadPodcastChecklistFromDisk(),
@@ -5172,6 +5519,14 @@ Promise.all([
       }
     }, 60 * 60 * 1000)
 
+    // Send study reminder emails for newly released lessons every hour
+    setInterval(() => {
+      scheduleStudyReminders().catch(err => {
+        console.error('[study-reminders] failed to schedule reminders:', err)
+      })
+    }, 60 * 60 * 1000)
+    void scheduleStudyReminders()
+
     app.listen(PORT, () => {
       logResendEmailAlignmentWarnings()
       console.log(`Portfolio app listening on http://localhost:${PORT}`)