@@ -24,9 +24,7 @@ export function HeroChatReply({ content, onOpenWorkflowResource }: HeroChatReply
               <>
                 {paragraph.slice(0, resourceIndex)}
                 <ResourceMention
-                  icon={
-                    <Workflow className='relative top-0.5 size-[12px] shrink-0 text-[var(--text-icon)]' />
-                  }
+                  icon={<Workflow className='size-[12px] shrink-0 text-[var(--text-icon)]' />}
                   title={WORKFLOW_TITLE}
                   onSelect={onOpenWorkflowResource}
                 />
 
@@ -0,0 +1,50 @@
+/** @vitest-environment node */
+import { NextRequest } from 'next/server'
+import { beforeEach, describe, expect, it, vi } from 'vitest'
+
+const mocks = vi.hoisted(() => ({
+  fetch: vi.fn(),
+  get: vi.fn(),
+  set: vi.fn(),
+}))
+vi.mock('@/lib/auth', () => ({ getSession: async () => ({ user: { id: 'test-user' } }) }))
+vi.mock('@/lib/core/rate-limiter/route-helpers', () => ({
+  enforceUserRateLimit: async () => null,
+}))
+vi.mock('@/lib/api/server', () => ({
+  parseRequest: async () => ({
+    success: true,
+    data: { query: { url: 'https://example.com/guide' } },
+  }),
+}))
+vi.mock('@/lib/core/config/redis', () => ({ getRedisClient: () => mocks }))
+vi.mock('@/lib/core/network/context.server', () => ({
+  runWithOutboundOrganization: (_organization: null, run: () => unknown) => run(),
+}))
+vi.mock('@/lib/core/utils/with-route-handler', () => ({
+  withRouteHandler: (handler: unknown) => handler,
+}))
+vi.mock('@/lib/link-preview/fetch-preview', () => ({ fetchLinkPreview: mocks.fetch }))
+
+import { GET } from '@/app/api/link-preview/route'
+
+const complete = { title: 'Guide', description: null, siteName: null }
+
+describe('link preview cache lifetime', () => {
+  beforeEach(() => {
+    vi.clearAllMocks()
+    mocks.get.mockResolvedValue(null)
+    mocks.set.mockResolvedValue('OK')
+  })
+
+  it.each([
+    { preview: { ...complete, imageRetryable: true }, ttl: 60 },
+    { preview: complete, ttl: 24 * 60 * 60 },
+    { preview: null, ttl: 60 * 60 },
+  ])('caches $preview for $ttl seconds', async ({ preview, ttl }) => {
+    mocks.fetch.mockResolvedValue(preview)
+    const response = await GET(new NextRequest('https://example.com/api/link-preview'))
+    expect(await response.json()).toEqual({ preview })
+    expect(mocks.set).toHaveBeenCalledWith(expect.any(String), JSON.stringify(preview), 'EX', ttl)
+  })
+})
@@ -1,8 +1,6 @@
 import { createHash } from 'crypto'
 import { createLogger } from '@sim/logger'
 import { getErrorMessage } from '@sim/utils/errors'
-import { truncate } from '@sim/utils/string'
-import * as cheerio from 'cheerio'
 import type { NextRequest } from 'next/server'
 import { NextResponse } from 'next/server'
 import type { LinkPreview } from '@/lib/api/contracts/link-preview'
@@ -12,66 +10,15 @@ import { getSession } from '@/lib/auth'
 import { getRedisClient } from '@/lib/core/config/redis'
 import { runWithOutboundOrganization } from '@/lib/core/network/context.server'
 import { enforceUserRateLimit } from '@/lib/core/rate-limiter/route-helpers'
-import { secureFetchWithValidation } from '@/lib/core/security/input-validation.server'
 import { withRouteHandler } from '@/lib/core/utils/with-route-handler'
+import { fetchLinkPreview } from '@/lib/link-preview/fetch-preview'
 
 const logger = createLogger('LinkPreviewAPI')
 
-const FETCH_TIMEOUT_MS = 5000
-const MAX_RESPONSE_BYTES = 256 * 1024
-const MAX_REDIRECTS = 3
-const TITLE_MAX_CHARS = 200
-const DESCRIPTION_MAX_CHARS = 300
 const CACHE_TTL_SECONDS = 24 * 60 * 60
 const NEGATIVE_CACHE_TTL_SECONDS = 60 * 60
-const CACHE_KEY_PREFIX = 'link-preview:v1:'
-
-/**
- * Parses preview metadata from the fetched document (already capped at
- * MAX_RESPONSE_BYTES); cheerio handles attribute order, quoting, and entity
- * decoding.
- */
-function parsePreview(html: string): LinkPreview {
-  const $ = cheerio.load(html)
-
-  const meta = (key: string): string | null => {
-    const value = $(`meta[property="${key}"], meta[name="${key}"]`).first().attr('content')
-    return value?.trim() || null
-  }
-
-  const title =
-    meta('og:title') ?? meta('twitter:title') ?? ($('title').first().text().trim() || null)
-  const description = meta('og:description') ?? meta('twitter:description') ?? meta('description')
-  const siteName = meta('og:site_name')
-
-  if (!title && !description && !siteName) return null
-  return {
-    title: title ? truncate(title, TITLE_MAX_CHARS) : null,
-    description: description ? truncate(description, DESCRIPTION_MAX_CHARS) : null,
-    siteName: siteName ? truncate(siteName, TITLE_MAX_CHARS) : null,
-  }
-}
-
-async function fetchPreview(url: string): Promise<LinkPreview> {
-  const response = await secureFetchWithValidation(url, {
-    // The URL is harvested from a rendered link rather than authored as a
-    // destination, so it gets no reach into a private network.
-    profile: 'contentFetch',
-    timeout: FETCH_TIMEOUT_MS,
-    maxRedirects: MAX_REDIRECTS,
-    maxResponseBytes: MAX_RESPONSE_BYTES,
-    headers: {
-      'User-Agent': 'Simbot/1.0 (+https://sim.ai)',
-      Accept: 'text/html,application/xhtml+xml',
-    },
-  })
-  if (response.status < 200 || response.status >= 300) return null
-  const contentType = response.headers.get('content-type') ?? ''
-  if (!contentType.includes('text/html') && !contentType.includes('application/xhtml+xml')) {
-    return null
-  }
-  return parsePreview(await response.text())
-}
+const RETRYABLE_CACHE_TTL_SECONDS = 60
+const CACHE_KEY_PREFIX = 'link-preview:v2:'
 
 export const GET = withRouteHandler(async (request: NextRequest) => {
   const session = await getSession()
@@ -106,16 +53,21 @@ export const GET = withRouteHandler(async (request: NextRequest) => {
   let preview: LinkPreview = null
   try {
     /** Link previews have no organization owner and use a shared URL cache. */
-    preview = await runWithOutboundOrganization(null, () => fetchPreview(url))
+    preview = await runWithOutboundOrganization(null, () => fetchLinkPreview(url, request.signal))
   } catch (error) {
+    if (request.signal.aborted) return new NextResponse(null, { status: 499 })
     logger.info('Link preview fetch failed; returning null preview', {
       host: new URL(url).hostname,
       error: getErrorMessage(error, 'unknown error').replaceAll(url, '[url]'),
     })
   }
 
   if (redis) {
-    const ttl = preview ? CACHE_TTL_SECONDS : NEGATIVE_CACHE_TTL_SECONDS
+    const ttl = preview?.imageRetryable
+      ? RETRYABLE_CACHE_TTL_SECONDS
+      : preview
+        ? CACHE_TTL_SECONDS
+        : NEGATIVE_CACHE_TTL_SECONDS
     try {
       await redis.set(cacheKey, JSON.stringify(preview), 'EX', ttl)
     } catch (error) {
 
@@ -10,6 +10,7 @@ import {
   isAssistantImageType,
 } from '@/lib/uploads/shared/assistant-images'
 import { MOTHERSHIP_ACCEPT_ATTRIBUTE } from '@/lib/uploads/utils/validation'
+import { inter } from '@/app/_styles/fonts/inter/inter'
 import { SearchInputBar } from '@/app/o/[organizationId]/components/search-input-bar'
 import { useOrganizationContext } from '@/app/o/[organizationId]/providers/organization-provider'
 import { AttachedFilesList } from '@/app/workspace/[workspaceId]/home/components/user-input/components/attached-files-list/attached-files-list'
@@ -280,6 +281,7 @@ export function Composer({
       onDragOver={files.handleDragOver}
       onDrop={files.handleDrop}
       className={cn(
+        inter.className,
         'relative z-10 mx-auto w-full max-w-chat',
         !imagesOnly &&
           'rounded-2xl border border-[var(--border-1)] bg-[var(--white)] px-2.5 py-2 dark:bg-[var(--surface-4)]',
 
@@ -31,6 +31,7 @@ vi.mock('next/navigation', () => ({
   usePathname: () => '/workspace/workspace-1/files',
   useRouter: () => ({ push: vi.fn() }),
 }))
+vi.mock('@/app/_styles/fonts/inter/inter', () => ({ inter: { variable: 'test-inter-variable' } }))
 vi.mock('@/lib/auth/auth-client', () => ({ useSession: () => ({ data: null, isPending: false }) }))
 vi.mock('@/hooks/queries/workspace-files', () => ({
   useUploadWorkspaceFile: () => ({ mutateAsync: uploadFile }),
 
@@ -25,6 +25,7 @@ import {
 } from '@/lib/mothership/chat/selection-context'
 import type { FileDownloadSource } from '@/lib/uploads/client/download'
 import type { WorkspaceFileRecord } from '@/lib/uploads/contexts/workspace'
+import { inter } from '@/app/_styles/fonts/inter/inter'
 import { FindBar } from '@/app/workspace/[workspaceId]/components/find-bar/find-bar'
 import { FileSaveConflict } from '@/app/workspace/[workspaceId]/files/components/file-viewer/file-save-conflict'
 import { PreviewLoadingFrame } from '@/app/workspace/[workspaceId]/files/components/file-viewer/preview-shared'
@@ -118,8 +119,10 @@ function warnRichMarkdownPasteLimit(reason?: 'paste' | 'formatting') {
  * {@link ReadOnlyPlaceholder} render into, so the two are geometrically identical and the placeholder →
  * live swap never reflows. Shared as one constant to keep them in lockstep.
  */
-const EDITOR_SURFACE_CLASS =
-  'mx-auto flex w-full max-w-[48rem] flex-1 flex-col px-8 py-6 selection:bg-[var(--selection-bg)] selection:text-[var(--text-primary)] dark:selection:bg-[var(--selection-dark)] dark:selection:text-white'
+const EDITOR_SURFACE_CLASS = cn(
+  'mx-auto flex w-full max-w-[48rem] flex-1 flex-col px-8 py-6 selection:bg-[var(--selection-bg)] selection:text-[var(--text-primary)] dark:selection:bg-[var(--selection-dark)] dark:selection:text-white',
+  inter.variable
+)
 
 /** ProseMirror block positions do not correspond to markdown source line numbers. */
 function buildEditorSelectionContext(
 
@@ -1,14 +1,13 @@
-import { cn, Lightbox } from '@sim/emcn'
+import { ChipTag, cn, Lightbox, OverflowText } from '@sim/emcn'
 import { getDocumentIcon } from '@/components/icons/document-icons'
 import type { ChatMessageAttachment } from '@/app/workspace/[workspaceId]/home/types'
 
 function FileAttachmentPill(props: { mediaType: string; filename: string }) {
   const Icon = getDocumentIcon(props.mediaType, props.filename)
   return (
-    <div className='flex max-w-[140px] items-center gap-[5px] rounded-lg bg-[var(--surface-5)] px-[6px] py-[3px]'>
-      <Icon className='size-[14px] shrink-0 text-[var(--text-icon)]' />
-      <span className='truncate text-[var(--text-body)] text-xs'>{props.filename}</span>
-    </div>
+    <ChipTag variant='mono' leftIcon={Icon} className='max-w-[140px]'>
+      <OverflowText label={props.filename} />
+    </ChipTag>
   )
 }
 
 
@@ -59,7 +59,7 @@ export function ActivityDisclosure({
       {collapsible && (
         <Expandable expanded={expanded}>
           <ExpandableContent id={contentId}>
-            <div className='pt-1.5'>
+            <div className='pt-2'>
               <ActivityViewport isStreaming={isStreaming} unbounded={unbounded}>
                 {children}
               </ActivityViewport>
 
@@ -80,7 +80,7 @@ describe('flat expanded activity layout', () => {
         expect(iconSlot(row).classList).toContain(ICON_SLOT)
       }
       const list = rows[0].closest('.flex-col')!
-      expect(list.classList).toContain('gap-1.5')
+      expect(list.classList).toContain('gap-2')
       let node: Element | null = rows[0]
       while (node && node !== container) {
         expect(hasIndent(node), node.className).toBe(false)
@@ -134,16 +134,15 @@ describe('flat expanded activity layout', () => {
         },
       },
     ])
-    const blocks = container.querySelector('.flex-col.gap-3')!
+    const blocks = container.querySelector('.flex-col.gap-2')!
     expect(blocks.contains(statuses()[0])).toBe(true)
-    expect(blocks.classList).toContain('gap-3')
-    expect(blocks.classList).not.toContain('gap-1.5')
+    expect(blocks.classList).toContain('gap-2')
     expect(statuses()).toHaveLength(1)
     expand()
     const rows = statuses().slice(1)
     expect(rows).toHaveLength(3)
     for (const row of rows) {
-      expect(row.closest('.flex-col')!.classList).toContain('gap-1.5')
+      expect(row.closest('.flex-col')!.classList).toContain('gap-2')
       expect(iconSlot(row).classList).toContain(ICON_SLOT)
     }
   })
 
@@ -85,8 +85,7 @@ export function ActivityViewport({
       className={cn(
         'pr-2',
         !unbounded && 'scrollbar-hide max-h-[110px] overflow-y-auto',
-        scrollFadeClass,
-        (edges.top || edges.bottom) && 'py-1'
+        scrollFadeClass
       )}
       {...scrollFadeAttributes(edges)}
     >