diff --git a/apps/web/src/lib/server/__tests__/markdown-tiptap.test.ts b/apps/web/src/lib/server/__tests__/markdown-tiptap.test.ts
index 09c7c04af..d54487a84 100644
--- a/apps/web/src/lib/server/__tests__/markdown-tiptap.test.ts
+++ b/apps/web/src/lib/server/__tests__/markdown-tiptap.test.ts
@@ -2,6 +2,7 @@ import { describe, test, expect } from 'vitest'
 import {
   markdownToTiptapJson,
   tiptapJsonToMarkdown,
+  contentJsonToMarkdown,
   commentMarkdownToTiptapJson,
 } from '../markdown-tiptap'
 
@@ -177,6 +178,123 @@ describe('tiptapJsonToMarkdown', () => {
   })
 })
 
+describe('contentJsonToMarkdown', () => {
+  const imageDoc = {
+    type: 'doc' as const,
+    content: [
+      { type: 'paragraph', content: [{ type: 'text', text: 'Shipped a thing.' }] },
+      {
+        type: 'image',
+        attrs: { src: 'https://cdn.example.com/shot.png', alt: 'Screenshot', title: null },
+      },
+    ],
+  }
+
+  test('serializes image nodes the stored markdown dropped', () => {
+    // The reported bug: the API returned text-only markdown because the stored
+    // `content` column lost images. Deriving from contentJson restores them.
+    const result = contentJsonToMarkdown(imageDoc, 'Shipped a thing.')
+    expect(result).toContain('Shipped a thing.')
+    expect(result).toContain('![Screenshot](https://cdn.example.com/shot.png)')
+  })
+
+  test('serializes resizableImage nodes (the type the editor actually stores)', () => {
+    // UI uploads are stored as `resizableImage`, which @tiptap/markdown's Image
+    // extension does not know — they must be normalized to `image` first.
+    const resizableDoc = {
+      type: 'doc' as const,
+      content: [
+        { type: 'paragraph', content: [{ type: 'text', text: 'Look:' }] },
+        {
+          type: 'resizableImage',
+          attrs: { src: 'https://cdn.example.com/r.png', alt: 'Resized', title: null, width: 400 },
+        },
+      ],
+    }
+    const result = contentJsonToMarkdown(resizableDoc, 'Look:')
+    expect(result).toContain('![Resized](https://cdn.example.com/r.png)')
+  })
+
+  test('keeps mentions (as @label) when restoring an image', () => {
+    // The server manager has no mention extension, so re-serializing must not
+    // drop it; normalize it to the @label text instead.
+    const doc = {
+      type: 'doc' as const,
+      content: [
+        {
+          type: 'paragraph',
+          content: [
+            { type: 'text', text: 'cc ' },
+            { type: 'mention', attrs: { id: 'p1', label: 'Alice' } },
+          ],
+        },
+        { type: 'image', attrs: { src: 'https://cdn.example.com/s.png', alt: 'S', title: null } },
+      ],
+    }
+    const result = contentJsonToMarkdown(doc, 'cc @Alice')
+    expect(result).toContain('@Alice')
+    expect(result).toContain('![S](https://cdn.example.com/s.png)')
+  })
+
+  test('keeps stored markdown when an image coexists with an unsupported node', () => {
+    // A youtube embed has no server renderer; re-serializing would drop it, so
+    // the whole document keeps its stored markdown (image not re-derived) rather
+    // than losing the embed.
+    const doc = {
+      type: 'doc' as const,
+      content: [
+        { type: 'image', attrs: { src: 'https://cdn.example.com/s.png', alt: 'S', title: null } },
+        { type: 'youtube', attrs: { src: 'https://youtu.be/abc' } },
+      ],
+    }
+    const stored = 'stored markdown with :::youtube::: and no image'
+    expect(contentJsonToMarkdown(doc, stored)).toBe(stored)
+  })
+
+  test('returns the stored markdown verbatim for image-free content', () => {
+    // No images means the stored column is already faithful; don't re-serialize
+    // (and risk reformatting) what was correct.
+    const noImageDoc = {
+      type: 'doc' as const,
+      content: [{ type: 'paragraph', content: [{ type: 'text', text: 'Just text' }] }],
+    }
+    expect(contentJsonToMarkdown(noImageDoc, '_Just_ text')).toBe('_Just_ text')
+  })
+
+  test.each([null, undefined])(
+    'falls back to stored markdown when contentJson is %s (legacy rows)',
+    (value) => {
+      expect(contentJsonToMarkdown(value, '# Legacy\n\nPlain markdown')).toBe(
+        '# Legacy\n\nPlain markdown'
+      )
+    }
+  )
+
+  test('falls back when contentJson has no real content', () => {
+    expect(contentJsonToMarkdown({ type: 'doc', content: [] }, 'fallback text')).toBe(
+      'fallback text'
+    )
+  })
+
+  test('falls back instead of throwing on malformed contentJson', () => {
+    // A corrupt/unexpected shape must never 500 a read endpoint.
+    const malformed = { not: 'a real doc' } as unknown as Parameters<
+      typeof contentJsonToMarkdown
+    >[0]
+    expect(contentJsonToMarkdown(malformed, 'safe fallback')).toBe('safe fallback')
+  })
+
+  test.each([
+    ['content is a string', { type: 'doc', content: 'oops' }],
+    ['content is an object', { type: 'doc', content: { bad: 1 } }],
+  ])('falls back when %s (image scan must not throw)', (_label, doc) => {
+    // The image scan runs before the serialize try/catch, so a row whose
+    // `content` is present but not an array must not throw a read into a 500.
+    const malformed = doc as unknown as Parameters<typeof contentJsonToMarkdown>[0]
+    expect(contentJsonToMarkdown(malformed, 'safe fallback')).toBe('safe fallback')
+  })
+})
+
 describe('commentMarkdownToTiptapJson', () => {
   test('plain text becomes a paragraph', () => {
     const result = commentMarkdownToTiptapJson('Hello world')
diff --git a/apps/web/src/lib/server/domains/changelog/__tests__/changelog-notified-at.test.ts b/apps/web/src/lib/server/domains/changelog/__tests__/changelog-notified-at.test.ts
index 260cf85a7..9a1d82afd 100644
--- a/apps/web/src/lib/server/domains/changelog/__tests__/changelog-notified-at.test.ts
+++ b/apps/web/src/lib/server/domains/changelog/__tests__/changelog-notified-at.test.ts
@@ -232,6 +232,28 @@ describe('createChangelog wiring', () => {
 
     expect(dispatchChangelogPublished).not.toHaveBeenCalled()
   })
+
+  it('stores the markdown projection of contentJson so images reach the content column', async () => {
+    // Write-time regen: the stored `content` column must carry the image even
+    // when the caller-supplied markdown would have, so downstream consumers
+    // that read the column directly (webhooks, notifications) get it too.
+    const { createChangelog } = await import('../changelog.service')
+
+    await createChangelog(
+      {
+        title: 'X',
+        content: '![Shot](https://cdn.example.com/shot.png)',
+        publishState: { type: 'draft' },
+      },
+      AUTHOR
+    )
+
+    expect(mockInsertValues).toHaveBeenCalledWith(
+      expect.objectContaining({
+        content: expect.stringContaining('![Shot](https://cdn.example.com/shot.png)'),
+      })
+    )
+  })
 })
 
 describe('updateChangelog wiring', () => {
diff --git a/apps/web/src/lib/server/domains/changelog/changelog.service.ts b/apps/web/src/lib/server/domains/changelog/changelog.service.ts
index e26384560..9115f1cfb 100644
--- a/apps/web/src/lib/server/domains/changelog/changelog.service.ts
+++ b/apps/web/src/lib/server/domains/changelog/changelog.service.ts
@@ -25,7 +25,7 @@ import {
 } from '@/lib/server/db'
 import type { ChangelogId, PrincipalId, PostId } from '@quackback/ids'
 import { NotFoundError, ValidationError } from '@/lib/shared/errors'
-import { markdownToTiptapJson } from '@/lib/server/markdown-tiptap'
+import { markdownToTiptapJson, contentJsonToMarkdown } from '@/lib/server/markdown-tiptap'
 import { rehostExternalImages } from '@/lib/server/content/rehost-images'
 import {
   buildEventActor,
@@ -105,7 +105,9 @@ export async function createChangelog(
     .insert(changelogEntries)
     .values({
       title,
-      content,
+      // Store the markdown projection of the canonical contentJson so every
+      // consumer of the `content` column (webhooks, notifications) sees images.
+      content: contentJsonToMarkdown(contentJson, content),
       contentJson,
       principalId: author.principalId,
       publishedAt,
@@ -180,13 +182,21 @@ export async function updateChangelog(
   }
 
   if (input.title !== undefined) updateData.title = input.title.trim()
-  if (input.content !== undefined) updateData.content = input.content.trim()
   if (input.contentJson !== undefined || input.content !== undefined) {
     const parsed = input.contentJson ?? markdownToTiptapJson((input.content ?? '').trim())
-    updateData.contentJson = await rehostExternalImages(parsed, {
+    const contentJson = await rehostExternalImages(parsed, {
       contentType: 'changelog',
       principalId: existing.principalId ?? undefined,
     })
+    updateData.contentJson = contentJson
+    // Every content edit carries `input.content` (the API accepts only markdown;
+    // the editor emits markdown alongside contentJson), so the fallback reflects
+    // the new doc. `existing.content` is only a defensive default for a
+    // contentJson-only edit, which no caller makes.
+    updateData.content = contentJsonToMarkdown(
+      contentJson,
+      (input.content ?? existing.content).trim()
+    )
   }
 
   if (input.displayDate !== undefined) {
diff --git a/apps/web/src/lib/server/domains/help-center/__tests__/help-center-article.service.test.ts b/apps/web/src/lib/server/domains/help-center/__tests__/help-center-article.service.test.ts
index 72ba867b9..d7707143e 100644
--- a/apps/web/src/lib/server/domains/help-center/__tests__/help-center-article.service.test.ts
+++ b/apps/web/src/lib/server/domains/help-center/__tests__/help-center-article.service.test.ts
@@ -122,6 +122,7 @@ vi.mock('@/lib/server/db', () => ({
 
 vi.mock('@/lib/server/markdown-tiptap', () => ({
   markdownToTiptapJson: vi.fn(() => ({ type: 'doc', content: [] })),
+  contentJsonToMarkdown: (_json: unknown, fallback: string) => fallback,
 }))
 
 let getArticleById: typeof import('../help-center.article.service').getArticleById
diff --git a/apps/web/src/lib/server/domains/help-center/help-center.article.service.ts b/apps/web/src/lib/server/domains/help-center/help-center.article.service.ts
index 2131d3b64..eea670df3 100644
--- a/apps/web/src/lib/server/domains/help-center/help-center.article.service.ts
+++ b/apps/web/src/lib/server/domains/help-center/help-center.article.service.ts
@@ -14,7 +14,7 @@ import {
 import type { HelpCenterArticleId, HelpCenterCategoryId, PrincipalId } from '@quackback/ids'
 import { NotFoundError, ValidationError } from '@/lib/shared/errors'
 import { isTeamMember } from '@/lib/shared/roles'
-import { markdownToTiptapJson } from '@/lib/server/markdown-tiptap'
+import { markdownToTiptapJson, contentJsonToMarkdown } from '@/lib/server/markdown-tiptap'
 import { rehostExternalImages } from '@/lib/server/content/rehost-images'
 import { slugify } from '@/lib/shared/utils'
 import { uniqueHelpCenterSlug } from './help-center.slug'
@@ -182,7 +182,9 @@ export async function createArticle(
     .values({
       categoryId: input.categoryId as HelpCenterCategoryId,
       title,
-      content,
+      // Store the markdown projection of the canonical contentJson so the
+      // article list endpoint (which omits contentJson) still serves images.
+      content: contentJsonToMarkdown(contentJson, content),
       contentJson,
       slug,
       principalId: effectivePrincipalId,
@@ -209,13 +211,19 @@ export async function updateArticle(
   const updateData: Partial<typeof helpCenterArticles.$inferInsert> = { updatedAt: new Date() }
   if (input.title !== undefined) updateData.title = input.title.trim()
   if (input.content !== undefined || input.contentJson !== undefined) {
-    if (input.content !== undefined) {
-      updateData.content = input.content.trim()
-    }
     const parsed = input.contentJson ?? markdownToTiptapJson((input.content ?? '').trim())
-    updateData.contentJson = await rehostExternalImages(parsed, {
+    const contentJson = await rehostExternalImages(parsed, {
       contentType: 'help-center',
     })
+    updateData.contentJson = contentJson
+    if (input.content !== undefined) {
+      updateData.content = contentJsonToMarkdown(contentJson, input.content.trim())
+    } else {
+      // contentJson-only edit (no markdown source): refresh the stored column
+      // only when the tree carries images, else leave it as-is.
+      const regenerated = contentJsonToMarkdown(contentJson, '')
+      if (regenerated) updateData.content = regenerated
+    }
   }
   if (input.categoryId !== undefined)
     updateData.categoryId = input.categoryId as HelpCenterCategoryId
diff --git a/apps/web/src/lib/server/domains/posts/__tests__/post-create-service.test.ts b/apps/web/src/lib/server/domains/posts/__tests__/post-create-service.test.ts
index a24607e61..54f528326 100644
--- a/apps/web/src/lib/server/domains/posts/__tests__/post-create-service.test.ts
+++ b/apps/web/src/lib/server/domains/posts/__tests__/post-create-service.test.ts
@@ -143,6 +143,7 @@ vi.mock('@/lib/server/domains/activity/activity.service', () => ({
 
 vi.mock('@/lib/server/markdown-tiptap', () => ({
   markdownToTiptapJson: vi.fn(() => ({})),
+  contentJsonToMarkdown: (_json: unknown, fallback: string) => fallback,
 }))
 
 vi.mock('@/lib/server/content/rehost-images', () => ({
diff --git a/apps/web/src/lib/server/domains/posts/__tests__/post-tier-limits.test.ts b/apps/web/src/lib/server/domains/posts/__tests__/post-tier-limits.test.ts
index 49a0b8301..6b4548138 100644
--- a/apps/web/src/lib/server/domains/posts/__tests__/post-tier-limits.test.ts
+++ b/apps/web/src/lib/server/domains/posts/__tests__/post-tier-limits.test.ts
@@ -61,6 +61,7 @@ vi.mock('@/lib/server/domains/activity/activity.service', () => ({
 
 vi.mock('@/lib/server/markdown-tiptap', () => ({
   markdownToTiptapJson: vi.fn(() => ({})),
+  contentJsonToMarkdown: (_json: unknown, fallback: string) => fallback,
 }))
 
 vi.mock('@/lib/server/content/rehost-images', () => ({
diff --git a/apps/web/src/lib/server/domains/posts/__tests__/post.service-mentions.test.ts b/apps/web/src/lib/server/domains/posts/__tests__/post.service-mentions.test.ts
index 4ed730e01..e3c24c963 100644
--- a/apps/web/src/lib/server/domains/posts/__tests__/post.service-mentions.test.ts
+++ b/apps/web/src/lib/server/domains/posts/__tests__/post.service-mentions.test.ts
@@ -195,6 +195,7 @@ vi.mock('@/lib/server/domains/activity/activity.service', () => ({
 
 vi.mock('@/lib/server/markdown-tiptap', () => ({
   markdownToTiptapJson: vi.fn(() => ({ type: 'doc', content: [] })),
+  contentJsonToMarkdown: (_json: unknown, fallback: string) => fallback,
 }))
 
 vi.mock('@/lib/server/content/rehost-images', () => ({
diff --git a/apps/web/src/lib/server/domains/posts/post.service.ts b/apps/web/src/lib/server/domains/posts/post.service.ts
index b4cf47588..f668108cb 100644
--- a/apps/web/src/lib/server/domains/posts/post.service.ts
+++ b/apps/web/src/lib/server/domains/posts/post.service.ts
@@ -43,7 +43,7 @@ import {
 import { announcePublishedPost } from './post.announce'
 import { NotFoundError, ValidationError } from '@/lib/shared/errors'
 import { recordAuditEvent } from '@/lib/server/audit/log'
-import { markdownToTiptapJson } from '@/lib/server/markdown-tiptap'
+import { markdownToTiptapJson, contentJsonToMarkdown } from '@/lib/server/markdown-tiptap'
 import { rehostExternalImages } from '@/lib/server/content/rehost-images'
 import { subscribeToPost } from '@/lib/server/domains/subscriptions/subscription.service'
 import type { CreatePostInput, UpdatePostInput, CreatePostResult } from './post.types'
@@ -216,7 +216,9 @@ export async function createPost(
       .values({
         boardId: input.boardId,
         title,
-        content,
+        // Store the markdown projection of the canonical contentJson so every
+        // consumer of the `content` column (webhooks, notifications) sees images.
+        content: contentJsonToMarkdown(contentJson, content),
         contentJson,
         statusId,
         principalId: author.principalId,
@@ -375,13 +377,21 @@ export async function updatePost(
   // Build update data
   const updateData: Partial<Post> = {}
   if (input.title !== undefined) updateData.title = input.title.trim()
-  if (input.content !== undefined) updateData.content = input.content.trim()
   if (input.contentJson !== undefined || input.content !== undefined) {
     const parsed = input.contentJson ?? markdownToTiptapJson((input.content ?? '').trim())
-    updateData.contentJson = await rehostExternalImages(parsed, {
+    const contentJson = await rehostExternalImages(parsed, {
       contentType: 'post',
       principalId: existingPost.principalId,
     })
+    updateData.contentJson = contentJson
+    // Every content edit carries `input.content` (the API accepts only markdown;
+    // the editor emits markdown alongside contentJson), so the fallback reflects
+    // the new doc. `existingPost.content` is only a defensive default for a
+    // contentJson-only edit, which no caller makes.
+    updateData.content = contentJsonToMarkdown(
+      contentJson,
+      (input.content ?? existingPost.content).trim()
+    )
   }
   if (input.statusId !== undefined) updateData.statusId = input.statusId
   if (input.ownerPrincipalId !== undefined) updateData.ownerPrincipalId = input.ownerPrincipalId
diff --git a/apps/web/src/lib/server/markdown-tiptap.ts b/apps/web/src/lib/server/markdown-tiptap.ts
index 9a7ff62a6..fdf42c4df 100644
--- a/apps/web/src/lib/server/markdown-tiptap.ts
+++ b/apps/web/src/lib/server/markdown-tiptap.ts
@@ -72,6 +72,114 @@ export function tiptapJsonToMarkdown(json: TiptapContent | JSONContent): string
   return manager.serialize(json as JSONContent)
 }
 
+/**
+ * Image node types found in stored `contentJson`. The editor stores uploads as
+ * `resizableImage`; markdown parsed via {@link markdownToTiptapJson} yields the
+ * plain `image`. Mirrors `IMAGE_NODE_TYPES` in content/rehost-images.ts.
+ */
+const IMAGE_NODE_TYPES = new Set(['image', 'resizableImage'])
+
+/**
+ * Node types this module can faithfully turn into markdown: the server
+ * manager's own nodes (see SERVER_EXTENSIONS) plus the two we normalize below
+ * (`resizableImage` -> `image`, `mention` -> text). Anything else — `youtube`,
+ * `quackbackEmbed`, `emoji`, future custom nodes — would be silently dropped by
+ * the narrower server manager, so a document containing one keeps its stored
+ * markdown (which the client serialized with full coverage) instead.
+ */
+const RESERIALIZABLE_NODE_TYPES = new Set([
+  'doc',
+  'paragraph',
+  'text',
+  'heading',
+  'blockquote',
+  'bulletList',
+  'orderedList',
+  'listItem',
+  'codeBlock',
+  'horizontalRule',
+  'hardBreak',
+  'taskList',
+  'taskItem',
+  'table',
+  'tableRow',
+  'tableCell',
+  'tableHeader',
+  'image',
+  'resizableImage',
+  'mention',
+])
+
+/**
+ * Render an entity's markdown for output (API / MCP responses), preferring the
+ * stored `content` column but restoring images from the canonical `contentJson`.
+ *
+ * The stored markdown is faithful for everything except images: the editor's
+ * resizable-image node has no markdown serializer, so client-computed markdown
+ * silently dropped them. `contentJson` keeps the images (with rehosted src), so
+ * only when it carries an image do we re-serialize it to put them back as
+ * `![alt](src)`. Image-free content returns the stored markdown verbatim — no
+ * reason to pay for, or risk reformatting from, a re-serialize.
+ *
+ * Re-serialization runs through the narrower server manager, so we only do it
+ * when every node is representable (see {@link RESERIALIZABLE_NODE_TYPES}); a
+ * document mixing an image with, say, a YouTube embed keeps its stored markdown
+ * rather than dropping the embed. Also falls back when `contentJson` is absent
+ * (legacy rows / list queries that omit it) or can't be serialized — a read
+ * path must never fail over content shape.
+ */
+export function contentJsonToMarkdown(
+  contentJson: TiptapContent | JSONContent | null | undefined,
+  fallback: string
+): string {
+  if (!contentJson || !hasImageNode(contentJson) || !isReserializable(contentJson)) {
+    return fallback
+  }
+  try {
+    const markdown = tiptapJsonToMarkdown(normalizeForMarkdown(contentJson))
+    return markdown.trim() ? markdown : fallback
+  } catch {
+    return fallback
+  }
+}
+
+/**
+ * Depth-first scan for an image node (`image` or `resizableImage`) anywhere in a
+ * tree. Runs before the serialize try/catch, so it must stay total: a malformed
+ * row whose `content` is present but not an array must not throw.
+ */
+function hasImageNode(node: JSONContent): boolean {
+  if (typeof node.type === 'string' && IMAGE_NODE_TYPES.has(node.type)) return true
+  return Array.isArray(node.content) ? node.content.some(hasImageNode) : false
+}
+
+/**
+ * True only when every node in the tree can be re-serialized without loss. A
+ * single unknown node type makes this false so the caller keeps stored markdown.
+ * Total by the same contract as {@link hasImageNode}.
+ */
+function isReserializable(node: JSONContent): boolean {
+  if (typeof node.type === 'string' && !RESERIALIZABLE_NODE_TYPES.has(node.type)) return false
+  return Array.isArray(node.content) ? node.content.every(isReserializable) : true
+}
+
+/**
+ * Rewrite the editor's custom nodes into ones @tiptap/markdown can serialize:
+ * `resizableImage` -> `image` (shares src/alt but has no markdown spec) and
+ * `mention` -> the `@label` text the directive would otherwise hide. Only
+ * called once {@link isReserializable} has cleared the tree.
+ */
+function normalizeForMarkdown(node: JSONContent): JSONContent {
+  if (node.type === 'mention') {
+    const attrs = node.attrs ?? {}
+    const label = (attrs.label as string) || (attrs.id as string) || 'mention'
+    return { type: 'text', text: `@${label}` }
+  }
+  const next = node.type === 'resizableImage' ? { ...node, type: 'image' } : node
+  if (!Array.isArray(next.content)) return next
+  return { ...next, content: next.content.map(normalizeForMarkdown) }
+}
+
 /**
  * Slim extension set for comments — no images, no tables, no YouTube.
  * Comments are short, dense, and inline; we want the safe subset only.
diff --git a/apps/web/src/lib/server/mcp/tools.ts b/apps/web/src/lib/server/mcp/tools.ts
index 62cb7bf3e..10201807b 100644
--- a/apps/web/src/lib/server/mcp/tools.ts
+++ b/apps/web/src/lib/server/mcp/tools.ts
@@ -94,6 +94,8 @@ import {
 import { isFeatureEnabled } from '@/lib/server/domains/settings/settings.service'
 import { DomainException } from '@/lib/shared/errors'
 import { parseOptionalTypeId } from '@/lib/server/domains/api/validation'
+import { contentJsonToMarkdown } from '@/lib/server/markdown-tiptap'
+import type { TiptapContent } from '@/lib/server/db'
 import { realEmail } from '@/lib/shared/anonymous-email'
 import type { McpAuthContext, McpScope } from './types'
 import type {
@@ -216,6 +218,7 @@ function articleResult(article: {
   slug: string
   title: string
   content: string
+  contentJson: TiptapContent | null
   description: string | null
   position: number | null
   category: { id: string; slug: string; name: string }
@@ -231,7 +234,7 @@ function articleResult(article: {
     id: article.id,
     slug: article.slug,
     title: article.title,
-    content: article.content,
+    content: contentJsonToMarkdown(article.contentJson, article.content),
     description: article.description,
     position: article.position,
     category: article.category,
@@ -2481,7 +2484,7 @@ async function getPostDetails(postId: PostId): Promise<CallToolResult> {
   return jsonResult({
     id: post.id,
     title: post.title,
-    content: post.content,
+    content: contentJsonToMarkdown(post.contentJson, post.content),
     voteCount: post.voteCount,
     commentCount: post.commentCount,
     boardId: post.boardId,
@@ -2525,7 +2528,7 @@ async function getChangelogDetails(changelogId: ChangelogId): Promise<CallToolRe
   return jsonResult({
     id: entry.id,
     title: entry.title,
-    content: entry.content,
+    content: contentJsonToMarkdown(entry.contentJson, entry.content),
     status: entry.status,
     authorName: entry.author?.name ?? null,
     linkedPosts: entry.linkedPosts.map((p) => ({
diff --git a/apps/web/src/routes/api/v1/apps/posts.ts b/apps/web/src/routes/api/v1/apps/posts.ts
index 9c2fbc2c2..39f7e4be2 100644
--- a/apps/web/src/routes/api/v1/apps/posts.ts
+++ b/apps/web/src/routes/api/v1/apps/posts.ts
@@ -3,6 +3,7 @@ import { z } from 'zod'
 import { withApiKeyAuth } from '@/lib/server/domains/api/auth'
 import { badRequestResponse, handleDomainError } from '@/lib/server/domains/api/responses'
 import { parseTypeId } from '@/lib/server/domains/api/validation'
+import { contentJsonToMarkdown } from '@/lib/server/markdown-tiptap'
 import type { BoardId, PostId } from '@quackback/ids'
 import { appJsonResponse, preflightResponse } from '@/lib/server/integrations/apps/cors'
 import { segmentIdsForPrincipal } from '@/lib/server/domains/segments/segment-membership.service'
@@ -117,7 +118,7 @@ export const Route = createFileRoute('/api/v1/apps/posts')({
             {
               id: result.id,
               title: result.title,
-              content: result.content,
+              content: contentJsonToMarkdown(result.contentJson, result.content),
               voteCount: result.voteCount,
               boardId: result.boardId,
               statusId: result.statusId,
diff --git a/apps/web/src/routes/api/v1/changelog/$entryId.ts b/apps/web/src/routes/api/v1/changelog/$entryId.ts
index 3b8240afb..98d256ac5 100644
--- a/apps/web/src/routes/api/v1/changelog/$entryId.ts
+++ b/apps/web/src/routes/api/v1/changelog/$entryId.ts
@@ -13,6 +13,8 @@ import {
   updateChangelog,
   deleteChangelog,
 } from '@/lib/server/domains/changelog/changelog.service'
+import { contentJsonToMarkdown } from '@/lib/server/markdown-tiptap'
+import type { TiptapContent } from '@/lib/server/db'
 import type { PublishState } from '@/lib/shared/schemas/changelog'
 import type { ChangelogId } from '@quackback/ids'
 
@@ -28,6 +30,7 @@ function formatChangelogResponse(entry: {
   id: string
   title: string
   content: string
+  contentJson: TiptapContent | null
   publishedAt: Date | null
   displayDate: Date | null
   createdAt: Date
@@ -36,7 +39,7 @@ function formatChangelogResponse(entry: {
   return {
     id: entry.id,
     title: entry.title,
-    content: entry.content,
+    content: contentJsonToMarkdown(entry.contentJson, entry.content),
     publishedAt: entry.publishedAt?.toISOString() || null,
     displayDate: entry.displayDate?.toISOString() || null,
     createdAt: entry.createdAt.toISOString(),
diff --git a/apps/web/src/routes/api/v1/changelog/__tests__/$entryId.test.ts b/apps/web/src/routes/api/v1/changelog/__tests__/$entryId.test.ts
new file mode 100644
index 000000000..a8a6ef90c
--- /dev/null
+++ b/apps/web/src/routes/api/v1/changelog/__tests__/$entryId.test.ts
@@ -0,0 +1,87 @@
+import { beforeEach, describe, expect, it, vi } from 'vitest'
+import type { ChangelogId } from '@quackback/ids'
+
+const mockWithApiKeyAuth = vi.fn()
+const mockGetChangelogById = vi.fn()
+
+vi.mock('@tanstack/react-router', () => ({
+  createFileRoute: vi.fn(() => (opts: unknown) => ({ options: opts })),
+}))
+vi.mock('@/lib/server/domains/api/auth', () => ({
+  withApiKeyAuth: (...args: unknown[]) => mockWithApiKeyAuth(...args),
+}))
+vi.mock('@/lib/server/domains/changelog/changelog.service', () => ({
+  getChangelogById: (...args: unknown[]) => mockGetChangelogById(...args),
+  updateChangelog: vi.fn(),
+  deleteChangelog: vi.fn(),
+}))
+
+// markdown-tiptap is intentionally NOT mocked — the point of these tests is the
+// real contentJson -> markdown serialization, including image nodes.
+
+import { Route } from '../$entryId'
+
+type RouteOpts = {
+  server: { handlers: { GET: (...args: unknown[]) => Promise<Response> } }
+}
+const GET = (Route as unknown as { options: RouteOpts }).options.server.handlers.GET
+
+const ENTRY_ID = 'changelog_01h455vb4pex5vsknk084sn02q' as unknown as ChangelogId
+
+function baseEntry() {
+  return {
+    id: ENTRY_ID,
+    title: 'Dark mode',
+    content: 'We shipped dark mode.',
+    contentJson: null as unknown,
+    publishedAt: new Date('2026-01-01T00:00:00.000Z'),
+    displayDate: null,
+    createdAt: new Date('2026-01-01T00:00:00.000Z'),
+    updatedAt: new Date('2026-01-01T00:00:00.000Z'),
+  }
+}
+
+describe('GET /api/v1/changelog/:entryId — markdown image output', () => {
+  beforeEach(() => {
+    vi.clearAllMocks()
+    mockWithApiKeyAuth.mockResolvedValue({ principalId: 'principal_x', role: 'team' })
+  })
+
+  it('renders images from contentJson as markdown that the stored content dropped', async () => {
+    mockGetChangelogById.mockResolvedValue({
+      ...baseEntry(),
+      // Stored markdown column lost the image (client serializer has no spec
+      // for the image node); contentJson is the source of truth.
+      content: 'We shipped dark mode.',
+      contentJson: {
+        type: 'doc',
+        content: [
+          { type: 'paragraph', content: [{ type: 'text', text: 'We shipped dark mode.' }] },
+          {
+            type: 'image',
+            attrs: { src: 'https://cdn.example.com/dark.png', alt: 'Dark mode', title: null },
+          },
+        ],
+      },
+    })
+
+    const res = await GET({ request: new Request('http://t/'), params: { entryId: ENTRY_ID } })
+    expect(res.status).toBe(200)
+    const json = await res.json()
+    expect(json.data.content).toContain('We shipped dark mode.')
+    expect(json.data.content).toContain('![Dark mode](https://cdn.example.com/dark.png)')
+  })
+
+  it('falls back to the stored content for legacy rows without contentJson', async () => {
+    mockGetChangelogById.mockResolvedValue({
+      ...baseEntry(),
+      content: '# Legacy entry\n\nPlain text.',
+      contentJson: null,
+    })
+
+    const res = await GET({ request: new Request('http://t/'), params: { entryId: ENTRY_ID } })
+    expect(res.status).toBe(200)
+    const json = await res.json()
+    expect(json.data.content).toBe('# Legacy entry\n\nPlain text.')
+  })
+})
diff --git a/apps/web/src/routes/api/v1/changelog/index.ts b/apps/web/src/routes/api/v1/changelog/index.ts
index 5ce5a31fc..0e3d6812c 100644
--- a/apps/web/src/routes/api/v1/changelog/index.ts
+++ b/apps/web/src/routes/api/v1/changelog/index.ts
@@ -10,6 +10,7 @@ import {
 import { createChangelog } from '@/lib/server/domains/changelog/changelog.service'
 import { listChangelogs } from '@/lib/server/domains/changelog/changelog.query'
 import { publishedAtToPublishState } from '@/lib/shared/schemas/changelog'
+import { contentJsonToMarkdown } from '@/lib/server/markdown-tiptap'
 import { db, principal, eq } from '@/lib/server/db'
 import type { PostId } from '@quackback/ids'
 
@@ -52,7 +53,7 @@ export const Route = createFileRoute('/api/v1/changelog/')({
             result.items.map((entry) => ({
               id: entry.id,
               title: entry.title,
-              content: entry.content,
+              content: contentJsonToMarkdown(entry.contentJson, entry.content),
               publishedAt: entry.publishedAt?.toISOString() || null,
               displayDate: entry.displayDate?.toISOString() || null,
               createdAt: entry.createdAt.toISOString(),
@@ -113,7 +114,7 @@ export const Route = createFileRoute('/api/v1/changelog/')({
           return createdResponse({
             id: entry.id,
             title: entry.title,
-            content: entry.content,
+            content: contentJsonToMarkdown(entry.contentJson, entry.content),
             publishedAt: entry.publishedAt?.toISOString() || null,
             displayDate: entry.displayDate?.toISOString() || null,
             createdAt: entry.createdAt.toISOString(),
diff --git a/apps/web/src/routes/api/v1/help-center/articles/$articleId.ts b/apps/web/src/routes/api/v1/help-center/articles/$articleId.ts
index fe3feebe5..88b862ab5 100644
--- a/apps/web/src/routes/api/v1/help-center/articles/$articleId.ts
+++ b/apps/web/src/routes/api/v1/help-center/articles/$articleId.ts
@@ -17,6 +17,8 @@ import {
   unpublishArticle,
   deleteArticle,
 } from '@/lib/server/domains/help-center/help-center.service'
+import { contentJsonToMarkdown } from '@/lib/server/markdown-tiptap'
+import type { TiptapContent } from '@/lib/server/db'
 import type { HelpCenterArticleId, PrincipalId } from '@quackback/ids'
 
 const updateArticleBody = z.object({
@@ -35,6 +37,7 @@ function formatArticle(article: {
   title: string
   description: string | null
   content: string
+  contentJson: TiptapContent | null
   publishedAt: Date | null
   viewCount: number
   helpfulCount: number
@@ -49,7 +52,9 @@ function formatArticle(article: {
     slug: article.slug,
     title: article.title,
     description: article.description,
-    content: article.content,
+    // Render markdown from the canonical contentJson so images survive; falls
+    // back to the stored column for legacy rows.
+    content: contentJsonToMarkdown(article.contentJson, article.content),
     publishedAt: article.publishedAt?.toISOString() || null,
     viewCount: article.viewCount,
     helpfulCount: article.helpfulCount,
diff --git a/apps/web/src/routes/api/v1/help-center/articles/index.ts b/apps/web/src/routes/api/v1/help-center/articles/index.ts
index 89854c04f..fae05fa06 100644
--- a/apps/web/src/routes/api/v1/help-center/articles/index.ts
+++ b/apps/web/src/routes/api/v1/help-center/articles/index.ts
@@ -12,6 +12,8 @@ import {
 import { parseOptionalTypeId } from '@/lib/server/domains/api/validation'
 import { isFeatureEnabled } from '@/lib/server/domains/settings/settings.service'
 import { listArticles, createArticle } from '@/lib/server/domains/help-center/help-center.service'
+import { contentJsonToMarkdown } from '@/lib/server/markdown-tiptap'
+import type { TiptapContent } from '@/lib/server/db'
 import type { PrincipalId } from '@quackback/ids'
 
 const createArticleBody = z.object({
@@ -29,6 +31,7 @@ function formatArticle(article: {
   title: string
   description: string | null
   content: string
+  contentJson: TiptapContent | null
   publishedAt: Date | null
   viewCount: number
   helpfulCount: number
@@ -43,7 +46,10 @@ function formatArticle(article: {
     slug: article.slug,
     title: article.title,
     description: article.description,
-    content: article.content,
+    // Render markdown from the canonical contentJson so images survive; falls
+    // back to the stored column for legacy rows (and the list query, which
+    // omits contentJson for performance).
+    content: contentJsonToMarkdown(article.contentJson, article.content),
     publishedAt: article.publishedAt?.toISOString() || null,
     viewCount: article.viewCount,
     helpfulCount: article.helpfulCount,
@@ -100,7 +106,11 @@ export const Route = createFileRoute('/api/v1/help-center/articles/')({
 
           const { authorId, ...articleData } = parsed.data
 
-          const authorPrincipalId = parseOptionalTypeId<PrincipalId>(authorId, 'principal', 'author ID')
+          const authorPrincipalId = parseOptionalTypeId<PrincipalId>(
+            authorId,
+            'principal',
+            'author ID'
+          )
 
           const article = await createArticle(
             articleData,
diff --git a/apps/web/src/routes/api/v1/posts/$postId.ts b/apps/web/src/routes/api/v1/posts/$postId.ts
index d5e6a3cd5..fb5b69a6c 100644
--- a/apps/web/src/routes/api/v1/posts/$postId.ts
+++ b/apps/web/src/routes/api/v1/posts/$postId.ts
@@ -13,6 +13,7 @@ import {
   parseOptionalTypeId,
   parseTypeIdArray,
 } from '@/lib/server/domains/api/validation'
+import { contentJsonToMarkdown } from '@/lib/server/markdown-tiptap'
 import type { PostId, StatusId, TagId, PrincipalId } from '@quackback/ids'
 import type { MergedPostSummary } from '@/lib/server/domains/posts/post.types'
 
@@ -49,7 +50,7 @@ export const Route = createFileRoute('/api/v1/posts/$postId')({
           return successResponse({
             id: post.id,
             title: post.title,
-            content: post.content,
+            content: contentJsonToMarkdown(post.contentJson, post.content),
             contentJson: post.contentJson,
             voteCount: post.voteCount,
             commentCount: post.commentCount,
@@ -141,7 +142,7 @@ export const Route = createFileRoute('/api/v1/posts/$postId')({
           return successResponse({
             id: result.id,
             title: result.title,
-            content: result.content,
+            content: contentJsonToMarkdown(result.contentJson, result.content),
             contentJson: result.contentJson,
             voteCount: result.voteCount,
             boardId: result.boardId,
diff --git a/apps/web/src/routes/api/v1/posts/index.ts b/apps/web/src/routes/api/v1/posts/index.ts
index c96e714a5..9e8bf5603 100644
--- a/apps/web/src/routes/api/v1/posts/index.ts
+++ b/apps/web/src/routes/api/v1/posts/index.ts
@@ -13,6 +13,7 @@ import {
   parseOptionalTypeId,
   parseTypeIdArray,
 } from '@/lib/server/domains/api/validation'
+import { contentJsonToMarkdown } from '@/lib/server/markdown-tiptap'
 import type { BoardId, PrincipalId, StatusId, TagId } from '@quackback/ids'
 import { segmentIdsForPrincipal } from '@/lib/server/domains/segments/segment-membership.service'
 
@@ -91,7 +92,7 @@ export const Route = createFileRoute('/api/v1/posts/')({
             result.items.map((post) => ({
               id: post.id,
               title: post.title,
-              content: post.content,
+              content: contentJsonToMarkdown(post.contentJson, post.content),
               voteCount: post.voteCount,
               commentCount: post.commentCount,
               boardId: post.boardId,
@@ -239,7 +240,7 @@ export const Route = createFileRoute('/api/v1/posts/')({
           return createdResponse({
             id: result.id,
             title: result.title,
-            content: result.content,
+            content: contentJsonToMarkdown(result.contentJson, result.content),
             voteCount: result.voteCount,
             boardId: result.boardId,
             statusId: result.statusId,