diff --git a/src/components/dms/ActionsWrapper.tsx b/src/components/dms/ActionsWrapper.tsx
index c1f54e2394..3ed704f99d 100644
--- a/src/components/dms/ActionsWrapper.tsx
+++ b/src/components/dms/ActionsWrapper.tsx
@@ -1,7 +1,6 @@
 import {View} from 'react-native'
 import {type ChatBskyConvoDefs} from '@atproto/api'
-import {msg} from '@lingui/core/macro'
-import {useLingui} from '@lingui/react'
+import {useLingui} from '@lingui/react/macro'
 
 import {atoms as a} from '#/alf'
 import {MessageContextMenu} from '#/components/dms/MessageContextMenu'
@@ -15,7 +14,7 @@ export function ActionsWrapper({
   isFromSelf: boolean
   children: React.ReactNode
 }) {
-  const {_} = useLingui()
+  const {t: l} = useLingui()
 
   return (
     <MessageContextMenu message={message}>
@@ -32,7 +31,7 @@ export function ActionsWrapper({
               ]}
               accessible={true}
               accessibilityActions={[
-                {name: 'activate', label: _(msg`Open message options`)},
+                {name: 'activate', label: l`Open message options`},
               ]}
               onAccessibilityAction={() => trigger.control.open('full')}>
               {children}
diff --git a/src/components/dms/DateDivider.tsx b/src/components/dms/DateDivider.tsx
index dfc2d53da5..0a54de39fc 100644
--- a/src/components/dms/DateDivider.tsx
+++ b/src/components/dms/DateDivider.tsx
@@ -1,8 +1,6 @@
 import {memo} from 'react'
 import {View} from 'react-native'
-import {msg} from '@lingui/core/macro'
-import {useLingui} from '@lingui/react'
-import {Trans} from '@lingui/react/macro'
+import {Trans, useLingui} from '@lingui/react/macro'
 import {subDays} from 'date-fns'
 
 import {atoms as a, useTheme} from '#/alf'
@@ -29,7 +27,7 @@ const longDateFormatterWithYear = new Intl.DateTimeFormat(undefined, {
 })
 
 let DateDivider = ({date: dateStr}: {date: string}): React.ReactNode => {
-  const {_} = useLingui()
+  const {t: l} = useLingui()
   const t = useTheme()
 
   let date: string
@@ -42,9 +40,9 @@ let DateDivider = ({date: dateStr}: {date: string}): React.ReactNode => {
   const oneWeekAgo = subDays(today, 7)
 
   if (localDateString(today) === localDateString(timestamp)) {
-    date = _(msg`Today`)
+    date = l`Today`
   } else if (localDateString(yesterday) === localDateString(timestamp)) {
-    date = _(msg`Yesterday`)
+    date = l`Yesterday`
   } else {
     if (timestamp < oneWeekAgo) {
       if (timestamp.getFullYear() === today.getFullYear()) {
@@ -58,7 +56,7 @@ let DateDivider = ({date: dateStr}: {date: string}): React.ReactNode => {
   }
 
   return (
-    <View style={[a.w_full, a.my_lg]}>
+    <View style={[a.w_full, a.my_sm]}>
       <Text
         style={[
           a.text_xs,
@@ -68,11 +66,7 @@ let DateDivider = ({date: dateStr}: {date: string}): React.ReactNode => {
           a.px_md,
         ]}>
         <Trans>
-          <Text
-            style={[a.text_xs, t.atoms.text_contrast_medium, a.font_semi_bold]}>
-            {date}
-          </Text>{' '}
-          at {time}
+          {date} at {time}
         </Trans>
       </Text>
     </View>
diff --git a/src/components/dms/DateDivider_DEPRECATED.tsx b/src/components/dms/DateDivider_DEPRECATED.tsx
new file mode 100644
index 0000000000..dfc2d53da5
--- /dev/null
+++ b/src/components/dms/DateDivider_DEPRECATED.tsx
@@ -0,0 +1,82 @@
+import {memo} from 'react'
+import {View} from 'react-native'
+import {msg} from '@lingui/core/macro'
+import {useLingui} from '@lingui/react'
+import {Trans} from '@lingui/react/macro'
+import {subDays} from 'date-fns'
+
+import {atoms as a, useTheme} from '#/alf'
+import {Text} from '../Typography'
+import {localDateString} from './util'
+
+const timeFormatter = new Intl.DateTimeFormat(undefined, {
+  hour: 'numeric',
+  minute: 'numeric',
+})
+const weekdayFormatter = new Intl.DateTimeFormat(undefined, {
+  weekday: 'long',
+})
+const longDateFormatter = new Intl.DateTimeFormat(undefined, {
+  weekday: 'short',
+  month: 'long',
+  day: 'numeric',
+})
+const longDateFormatterWithYear = new Intl.DateTimeFormat(undefined, {
+  weekday: 'short',
+  month: 'long',
+  day: 'numeric',
+  year: 'numeric',
+})
+
+let DateDivider = ({date: dateStr}: {date: string}): React.ReactNode => {
+  const {_} = useLingui()
+  const t = useTheme()
+
+  let date: string
+  const time = timeFormatter.format(new Date(dateStr))
+
+  const timestamp = new Date(dateStr)
+
+  const today = new Date()
+  const yesterday = subDays(today, 1)
+  const oneWeekAgo = subDays(today, 7)
+
+  if (localDateString(today) === localDateString(timestamp)) {
+    date = _(msg`Today`)
+  } else if (localDateString(yesterday) === localDateString(timestamp)) {
+    date = _(msg`Yesterday`)
+  } else {
+    if (timestamp < oneWeekAgo) {
+      if (timestamp.getFullYear() === today.getFullYear()) {
+        date = longDateFormatter.format(timestamp)
+      } else {
+        date = longDateFormatterWithYear.format(timestamp)
+      }
+    } else {
+      date = weekdayFormatter.format(timestamp)
+    }
+  }
+
+  return (
+    <View style={[a.w_full, a.my_lg]}>
+      <Text
+        style={[
+          a.text_xs,
+          a.text_center,
+          t.atoms.bg,
+          t.atoms.text_contrast_medium,
+          a.px_md,
+        ]}>
+        <Trans>
+          <Text
+            style={[a.text_xs, t.atoms.text_contrast_medium, a.font_semi_bold]}>
+            {date}
+          </Text>{' '}
+          at {time}
+        </Trans>
+      </Text>
+    </View>
+  )
+}
+DateDivider = memo(DateDivider)
+export {DateDivider}
diff --git a/src/components/dms/MessageContextMenu.tsx b/src/components/dms/MessageContextMenu.tsx
index dda99c77e2..5cae1adfc8 100644
--- a/src/components/dms/MessageContextMenu.tsx
+++ b/src/components/dms/MessageContextMenu.tsx
@@ -2,8 +2,7 @@ import {memo, useCallback} from 'react'
 import {LayoutAnimation, Platform} from 'react-native'
 import * as Clipboard from 'expo-clipboard'
 import {type ChatBskyConvoDefs, RichText} from '@atproto/api'
-import {msg} from '@lingui/core/macro'
-import {useLingui} from '@lingui/react'
+import {useLingui} from '@lingui/react/macro'
 import {useQueryClient} from '@tanstack/react-query'
 
 import {useGoogleTranslate} from '#/lib/hooks/useGoogleTranslate'
@@ -15,10 +14,10 @@ import {useSession} from '#/state/session'
 import * as ContextMenu from '#/components/ContextMenu'
 import {type TriggerProps} from '#/components/ContextMenu/types'
 import {AfterReportDialog} from '#/components/dms/AfterReportDialog'
-import {BubbleQuestion_Stroke2_Corner0_Rounded as Translate} from '#/components/icons/Bubble'
+import {BubbleQuestion_Stroke2_Corner0_Rounded as TranslateIcon} from '#/components/icons/Bubble'
 import {Clipboard_Stroke2_Corner2_Rounded as ClipboardIcon} from '#/components/icons/Clipboard'
-import {Trash_Stroke2_Corner0_Rounded as Trash} from '#/components/icons/Trash'
-import {Warning_Stroke2_Corner0_Rounded as Warning} from '#/components/icons/Warning'
+import {Trash_Stroke2_Corner0_Rounded as TrashIcon} from '#/components/icons/Trash'
+import {Warning_Stroke2_Corner0_Rounded as WarningIcon} from '#/components/icons/Warning'
 import {ReportDialog} from '#/components/moderation/ReportDialog'
 import * as Prompt from '#/components/Prompt'
 import {usePromptControl} from '#/components/Prompt'
@@ -35,7 +34,7 @@ export let MessageContextMenu = ({
   message: ChatBskyConvoDefs.MessageView
   children: TriggerProps['children']
 }): React.ReactNode => {
-  const {_} = useLingui()
+  const {t: l} = useLingui()
   const ax = useAnalytics()
   const {currentAccount} = useSession()
   const queryClient = useQueryClient()
@@ -58,10 +57,10 @@ export let MessageContextMenu = ({
     )
 
     void Clipboard.setStringAsync(str)
-    Toast.show(_(msg`Copied to clipboard`), {
+    Toast.show(l`Copied to clipboard`, {
       type: 'success',
     })
-  }, [_, message.text, message.facets])
+  }, [l, message.text, message.facets])
 
   const onPressTranslateMessage = useCallback(() => {
     void translate(message.text, langPrefs.primaryLanguage)
@@ -79,11 +78,9 @@ export let MessageContextMenu = ({
     LayoutAnimation.configureNext(LayoutAnimation.Presets.easeInEaseOut)
     convo
       .deleteMessage(message.id)
-      .then(() =>
-        Toast.show(_(msg({message: 'Message deleted', context: 'toast'}))),
-      )
-      .catch(() => Toast.show(_(msg`Failed to delete message`)))
-  }, [_, convo, message.id])
+      .then(() => Toast.show(l({message: 'Message deleted', context: 'toast'})))
+      .catch(() => Toast.show(l`Failed to delete message`))
+  }, [l, convo, message.id])
 
   const onEmojiSelect = useCallback(
     (emoji: string) => {
@@ -96,17 +93,17 @@ export let MessageContextMenu = ({
       ) {
         convo
           .removeReaction(message.id, emoji)
-          .catch(() => Toast.show(_(msg`Failed to remove emoji reaction`)))
+          .catch(() => Toast.show(l`Failed to remove emoji reaction`))
       } else {
         if (hasReachedReactionLimit(message, currentAccount?.did)) return
         convo.addReaction(message.id, emoji).catch(() =>
-          Toast.show(_(msg`Failed to add emoji reaction`), {
+          Toast.show(l`Failed to add emoji reaction`, {
             type: 'error',
           }),
         )
       }
     },
-    [_, convo, message, currentAccount?.did],
+    [l, convo, message, currentAccount?.did],
   )
 
   const sender = convo.convo.members.find(
@@ -126,12 +123,10 @@ export let MessageContextMenu = ({
         )}
 
         <ContextMenu.Trigger
-          label={_(msg`Message options`)}
-          contentLabel={_(
-            msg`Message from @${
-              sender?.handle ?? 'unknown' // should always be defined
-            }: ${message.text}`,
-          )}>
+          label={l`Message options`}
+          contentLabel={l`Message from @${
+            sender?.handle ?? 'unknown' // should always be defined
+          }: ${message.text}`}>
           {children}
         </ContextMenu.Trigger>
 
@@ -140,17 +135,17 @@ export let MessageContextMenu = ({
             <>
               <ContextMenu.Item
                 testID="messageDropdownTranslateBtn"
-                label={_(msg`Translate`)}
+                label={l`Translate`}
                 onPress={onPressTranslateMessage}>
-                <ContextMenu.ItemText>{_(msg`Translate`)}</ContextMenu.ItemText>
-                <ContextMenu.ItemIcon icon={Translate} position="right" />
+                <ContextMenu.ItemText>{l`Translate`}</ContextMenu.ItemText>
+                <ContextMenu.ItemIcon icon={TranslateIcon} position="right" />
               </ContextMenu.Item>
               <ContextMenu.Item
                 testID="messageDropdownCopyBtn"
-                label={_(msg`Copy message text`)}
+                label={l`Copy message text`}
                 onPress={onCopyMessage}>
                 <ContextMenu.ItemText>
-                  {_(msg`Copy message text`)}
+                  {l`Copy message text`}
                 </ContextMenu.ItemText>
                 <ContextMenu.ItemIcon icon={ClipboardIcon} position="right" />
               </ContextMenu.Item>
@@ -159,23 +154,22 @@ export let MessageContextMenu = ({
           )}
           <ContextMenu.Item
             testID="messageDropdownDeleteBtn"
-            label={_(msg`Delete message for me`)}
+            label={l`Delete message for me`}
             onPress={() => deleteControl.open()}>
-            <ContextMenu.ItemText>{_(msg`Delete for me`)}</ContextMenu.ItemText>
-            <ContextMenu.ItemIcon icon={Trash} position="right" />
+            <ContextMenu.ItemText>{l`Delete for me`}</ContextMenu.ItemText>
+            <ContextMenu.ItemIcon icon={TrashIcon} position="right" />
           </ContextMenu.Item>
           {!isFromSelf && (
             <ContextMenu.Item
               testID="messageDropdownReportBtn"
-              label={_(msg`Report message`)}
+              label={l`Report message`}
               onPress={() => reportControl.open()}>
-              <ContextMenu.ItemText>{_(msg`Report`)}</ContextMenu.ItemText>
-              <ContextMenu.ItemIcon icon={Warning} position="right" />
+              <ContextMenu.ItemText>{l`Report`}</ContextMenu.ItemText>
+              <ContextMenu.ItemIcon icon={WarningIcon} position="right" />
             </ContextMenu.Item>
           )}
         </ContextMenu.Outer>
       </ContextMenu.Root>
-
       <ReportDialog
         control={reportControl}
         subject={{
@@ -198,14 +192,11 @@ export let MessageContextMenu = ({
           message,
         }}
       />
-
       <Prompt.Basic
         control={deleteControl}
-        title={_(msg`Delete message`)}
-        description={_(
-          msg`Are you sure you want to delete this message? The message will be deleted for you, but not for the other participant.`,
-        )}
-        confirmButtonCta={_(msg`Delete`)}
+        title={l`Delete message`}
+        description={l`Are you sure you want to delete this message? The message will be deleted for you, but not for the other participants.`}
+        confirmButtonCta={l`Delete`}
         confirmButtonColor="negative"
         onConfirm={onDelete}
       />
diff --git a/src/components/dms/MessageItem.tsx b/src/components/dms/MessageItem.tsx
index 386b85d7f9..384ce1d5cb 100644
--- a/src/components/dms/MessageItem.tsx
+++ b/src/components/dms/MessageItem.tsx
@@ -6,6 +6,8 @@ import {
   View,
 } from 'react-native'
 import Animated, {
+  FadeIn,
+  FadeOut,
   LayoutAnimationConfig,
   LinearTransition,
   ZoomIn,
@@ -16,217 +18,386 @@ import {
   ChatBskyConvoDefs,
   RichText as RichTextAPI,
 } from '@atproto/api'
-import {type I18n} from '@lingui/core'
-import {msg} from '@lingui/core/macro'
-import {useLingui} from '@lingui/react'
+import {plural} from '@lingui/core/macro'
+import {useLingui} from '@lingui/react/macro'
 
 import {sanitizeDisplayName} from '#/lib/strings/display-names'
+import {sanitizeHandle} from '#/lib/strings/handles'
 import {useConvoActive} from '#/state/messages/convo'
 import {type ConvoItem} from '#/state/messages/convo/types'
+import {useModerationOpts} from '#/state/preferences/moderation-opts'
 import {useSession} from '#/state/session'
-import {TimeElapsed} from '#/view/com/util/TimeElapsed'
 import {atoms as a, native, useTheme} from '#/alf'
 import {isOnlyEmoji} from '#/alf/typography'
 import {ActionsWrapper} from '#/components/dms/ActionsWrapper'
 import {InlineLinkText} from '#/components/Link'
+import * as ProfileCard from '#/components/ProfileCard'
 import {RichText} from '#/components/RichText'
 import {Text} from '#/components/Typography'
-import {IS_NATIVE} from '#/env'
+import type * as bsky from '#/types/bsky'
 import {DateDivider} from './DateDivider'
 import {MessageItemEmbed} from './MessageItemEmbed'
-import {localDateString} from './util'
+
+const AVATAR_SIZE = 28
+const CLUSTERED_MESSAGE_GAP = 2
+const BORDER_RADIUS = 18
+const SQUARED_BORDER_RADIUS = 4
+const DISPLAY_NAME_INSET = 22
+
+const CLUSTERED_MESSAGE_THRESHOLD_MS = 5 * 60 * 1000
+const MESSAGE_GAP_THRESHOLD_MS = 60 * 60 * 1000
+
+function isWithinCluster({
+  isPending,
+  adjacentMessage,
+  isFromSameSender,
+  currentSentAt,
+  direction,
+}: {
+  isPending: boolean
+  adjacentMessage:
+    | ChatBskyConvoDefs.MessageView
+    | ChatBskyConvoDefs.DeletedMessageView
+    | null
+  isFromSameSender: boolean
+  currentSentAt: string
+  direction: 'prev' | 'next'
+}): boolean {
+  if (!isFromSameSender) return true
+  if (isPending && adjacentMessage) return false
+  if (ChatBskyConvoDefs.isMessageView(adjacentMessage)) {
+    const thisDate = new Date(currentSentAt)
+    const adjDate = new Date(adjacentMessage.sentAt)
+    const diff =
+      direction === 'next'
+        ? adjDate.getTime() - thisDate.getTime()
+        : thisDate.getTime() - adjDate.getTime()
+    return diff > CLUSTERED_MESSAGE_THRESHOLD_MS
+  }
+  return true
+}
 
 let MessageItem = ({
   item,
+  isGroupChat = false,
+  profile,
 }: {
   item: ConvoItem & {type: 'message' | 'pending-message'}
+  isGroupChat?: boolean
+  profile?: bsky.profile.AnyProfileView
 }): React.ReactNode => {
   const t = useTheme()
   const {currentAccount} = useSession()
-  const {_} = useLingui()
+  const {t: l} = useLingui()
   const {convo} = useConvoActive()
+  const moderationOpts = useModerationOpts()
 
   const {message, nextMessage, prevMessage} = item
   const isPending = item.type === 'pending-message'
 
+  const displayName = sanitizeDisplayName(
+    profile?.displayName || sanitizeHandle(profile?.handle ?? ''),
+  )
+
   const isFromSelf = message.sender?.did === currentAccount?.did
 
+  const prevIsMessage = ChatBskyConvoDefs.isMessageView(prevMessage)
   const nextIsMessage = ChatBskyConvoDefs.isMessageView(nextMessage)
 
-  const isNextFromSelf =
-    nextIsMessage && nextMessage.sender?.did === currentAccount?.did
+  const isPrevFromSameSender =
+    prevIsMessage && prevMessage.sender?.did === message.sender?.did
+  const isNextFromSameSender =
+    nextIsMessage && nextMessage.sender?.did === message.sender?.did
 
-  const isNextFromSameSender = isNextFromSelf === isFromSelf
+  const isFirstInCluster = useMemo(
+    () =>
+      isWithinCluster({
+        isPending,
+        adjacentMessage: prevMessage,
+        isFromSameSender: isPrevFromSameSender,
+        currentSentAt: message.sentAt,
+        direction: 'prev',
+      }),
+    [isPending, prevMessage, isPrevFromSameSender, message.sentAt],
+  )
 
-  const isNewDay = useMemo(() => {
-    if (!prevMessage) return true
+  const isLastInCluster = useMemo(
+    () =>
+      isWithinCluster({
+        isPending,
+        adjacentMessage: nextMessage,
+        isFromSameSender: isNextFromSameSender,
+        currentSentAt: message.sentAt,
+        direction: 'next',
+      }),
+    [isPending, nextMessage, isNextFromSameSender, message.sentAt],
+  )
 
-    const thisDate = new Date(message.sentAt)
-    const prevDate = new Date(prevMessage.sentAt)
+  const hasLargeGapFromPrev =
+    !ChatBskyConvoDefs.isMessageView(prevMessage) ||
+    new Date(message.sentAt).getTime() -
+      new Date(prevMessage.sentAt).getTime() >
+      MESSAGE_GAP_THRESHOLD_MS
 
-    return localDateString(thisDate) !== localDateString(prevDate)
-  }, [message, prevMessage])
+  const showDateDivider = hasLargeGapFromPrev
 
-  const isLastMessageOfDay = useMemo(() => {
-    if (!nextMessage || !nextIsMessage) return true
+  const isInCluster = !(isFirstInCluster && isLastInCluster)
+  const isInMiddleOfCluster =
+    isInCluster && !isFirstInCluster && !isLastInCluster
 
-    const thisDate = new Date(message.sentAt)
-    const prevDate = new Date(nextMessage.sentAt)
+  const hasReactions = message.reactions && message.reactions.length > 0
+  const squaredBottomCorner =
+    !hasReactions && isInCluster && (isInMiddleOfCluster || isFirstInCluster)
+  const squaredTopCorner =
+    isInCluster && (isInMiddleOfCluster || isLastInCluster)
 
-    return localDateString(thisDate) !== localDateString(prevDate)
-  }, [message.sentAt, nextIsMessage, nextMessage])
-
-  const needsTail = isLastMessageOfDay || !isNextFromSameSender
-
-  const isLastInGroup = useMemo(() => {
-    // if this message is pending, it means the next message is pending too
-    if (isPending && nextMessage) {
-      return false
-    }
-
-    // or, if there's a 5 minute gap between this message and the next
-    if (ChatBskyConvoDefs.isMessageView(nextMessage)) {
-      const thisDate = new Date(message.sentAt)
-      const nextDate = new Date(nextMessage.sentAt)
-
-      const diff = nextDate.getTime() - thisDate.getTime()
-
-      // 5 minutes
-      return diff > 5 * 60 * 1000
-    }
-
-    return true
-  }, [message, nextMessage, isPending])
-
-  const pendingColor = t.palette.primary_200
+  const pendingColor = t.palette.primary_300
 
   const rt = useMemo(() => {
     return new RichTextAPI({text: message.text, facets: message.facets})
   }, [message.text, message.facets])
 
+  const hasEmbedAndText =
+    AppBskyEmbedRecord.isView(message.embed) && rt.text.length > 0
+
+  const avatar = profile ? (
+    <ProfileCard.Avatar
+      profile={profile}
+      size={AVATAR_SIZE}
+      moderationOpts={moderationOpts!}
+      disabledPreview
+    />
+  ) : (
+    <ProfileCard.AvatarPlaceholder size={AVATAR_SIZE} />
+  )
+
+  const groupedReactions = useMemo(() => {
+    const reactions = message.reactions ?? []
+    const grouped = new Map<
+      string,
+      {
+        value: string
+        senders: ChatBskyConvoDefs.ReactionViewSender[]
+        count: number
+      }
+    >()
+    for (const react of reactions) {
+      if (!react) continue
+      const existing = grouped.get(react.value)
+      if (existing) {
+        existing.senders.push(react.sender)
+        existing.count++
+      } else {
+        grouped.set(react.value, {
+          value: react.value,
+          senders: [react.sender],
+          count: 1,
+        })
+      }
+    }
+    return Array.from(grouped.values())
+  }, [message.reactions])
+
+  const reactions = useMemo(() => message.reactions ?? [], [message.reactions])
+
+  const reactionsLabel = useMemo(() => {
+    if (reactions.length === 0) return ''
+    if (reactions.length === 1) {
+      const reaction = reactions[0]
+      const sender = reaction.sender
+      if (sender.did === currentAccount?.did) {
+        return l`You reacted ${reaction.value}`
+      } else {
+        const senderDid = reaction.sender.did
+        const sender = convo.members.find(member => member.did === senderDid)
+        if (sender) {
+          return l`${sanitizeDisplayName(
+            sender.displayName || sender.handle,
+          )} reacted ${reaction.value}`
+        }
+        return l`Someone reacted ${reaction.value}`
+      }
+    }
+    return l`${plural(reactions.length, {
+      one: '# person',
+      other: '# people',
+    })} reacted – ${groupedReactions.map(g => g.value).join(' ')}`
+  }, [reactions, groupedReactions, currentAccount?.did, convo.members, l])
+
   const appliedReactions = (
     <LayoutAnimationConfig skipEntering skipExiting>
-      {message.reactions && message.reactions.length > 0 && (
+      {hasReactions ? (
         <View
-          style={[isFromSelf ? a.align_end : a.align_start, a.px_sm, a.pb_2xs]}>
+          style={[
+            isFromSelf ? a.align_end : a.align_start,
+            a.px_sm,
+            a.pb_2xs,
+            !isFromSelf && isGroupChat && {paddingLeft: AVATAR_SIZE},
+          ]}>
           <View
+            accessible={true}
+            accessibilityLabel={reactionsLabel}
+            accessibilityHint={l`Double tap or long press the message to add a reaction`}
             style={[
               a.flex_row,
               a.gap_2xs,
               a.py_xs,
               a.px_xs,
-              a.justify_center,
               isFromSelf ? a.justify_end : a.justify_start,
               a.flex_wrap,
-              a.pb_xs,
-              t.atoms.bg_contrast_25,
+              a.rounded_lg,
               a.border,
               t.atoms.border_contrast_low,
-              a.rounded_lg,
+              t.atoms.bg_contrast_25,
               t.atoms.shadow_sm,
               {
-                // vibe coded number
-                transform: [{translateY: -11}],
+                transform: [{translateY: -8}],
               },
             ]}>
-            {message.reactions.map((reaction, _i, reactions) => {
-              let label
-              if (reaction.sender.did === currentAccount?.did) {
-                label = _(msg`You reacted ${reaction.value}`)
-              } else {
-                const senderDid = reaction.sender.did
-                const sender = convo.members.find(
-                  member => member.did === senderDid,
-                )
-                if (sender) {
-                  label = _(
-                    msg`${sanitizeDisplayName(
-                      sender.displayName || sender.handle,
-                    )} reacted ${reaction.value}`,
-                  )
-                } else {
-                  label = _(msg`Someone reacted ${reaction.value}`)
+            {groupedReactions.map(group => (
+              <Animated.View
+                entering={native(ZoomIn.springify(200).delay(400))}
+                exiting={
+                  groupedReactions.length > 1 && native(ZoomOut.delay(200))
                 }
-              }
-              return (
-                <Animated.View
-                  entering={native(ZoomIn.springify(200).delay(400))}
-                  exiting={reactions.length > 1 && native(ZoomOut.delay(200))}
-                  layout={native(LinearTransition.delay(300))}
-                  key={reaction.sender.did + reaction.value}
-                  style={[a.p_2xs]}
-                  accessible={true}
-                  accessibilityLabel={label}
-                  accessibilityHint={_(
-                    msg`Double tap or long press the message to add a reaction`,
-                  )}>
-                  <Text emoji style={[a.text_sm]}>
-                    {reaction.value}
-                  </Text>
-                </Animated.View>
-              )
-            })}
+                layout={native(LinearTransition.delay(300))}
+                key={group.value}
+                style={[a.p_2xs]}>
+                <Text emoji style={[a.text_sm]}>
+                  {group.value}
+                </Text>
+              </Animated.View>
+            ))}
+            {groupedReactions.length !== reactions.length &&
+            reactions.length > 1 ? (
+              <View style={[a.p_2xs, a.justify_center]}>
+                <Text
+                  style={[
+                    a.text_xs,
+                    t.atoms.text_contrast_medium,
+                    {includeFontPadding: false},
+                  ]}>
+                  {reactions.length}
+                </Text>
+              </View>
+            ) : null}
           </View>
         </View>
-      )}
+      ) : null}
     </LayoutAnimationConfig>
   )
 
   return (
     <>
-      {isNewDay && <DateDivider date={message.sentAt} />}
+      {showDateDivider && (
+        <Animated.View entering={native(FadeIn)} exiting={native(FadeOut)}>
+          <DateDivider date={message.sentAt} />
+        </Animated.View>
+      )}
       <View
         style={[
-          isFromSelf ? a.mr_md : a.ml_md,
-          nextIsMessage && !isNextFromSameSender && a.mb_md,
+          isFromSelf ? a.mr_sm : a.ml_sm,
+          isFirstInCluster && !showDateDivider && a.mt_sm,
         ]}>
-        <ActionsWrapper isFromSelf={isFromSelf} message={message}>
-          {AppBskyEmbedRecord.isView(message.embed) && (
-            <MessageItemEmbed embed={message.embed} />
-          )}
-          {rt.text.length > 0 && (
-            <View
-              style={
-                !isOnlyEmoji(message.text) && [
-                  a.py_sm,
-                  a.my_2xs,
-                  a.rounded_md,
+        <View style={[a.relative]}>
+          {isGroupChat && !isFromSelf && isLastInCluster ? (
+            <View style={[a.absolute, a.bottom_0]}>{avatar}</View>
+          ) : null}
+          <View
+            style={[
+              a.flex_grow,
+              !isFromSelf &&
+                isGroupChat && {
+                  paddingLeft: AVATAR_SIZE,
+                },
+            ]}>
+            {isGroupChat &&
+            !isFromSelf &&
+            isFirstInCluster &&
+            !isOnlyEmoji(message.text) ? (
+              <Text
+                style={[
+                  a.text_xs,
+                  t.atoms.text_contrast_medium,
+                  a.pt_xs,
+                  a.pb_2xs,
                   {
-                    paddingLeft: 14,
-                    paddingRight: 14,
-                    backgroundColor: isFromSelf
-                      ? isPending
-                        ? pendingColor
-                        : t.palette.primary_500
-                      : t.palette.contrast_50,
-                    borderRadius: 17,
+                    paddingLeft: DISPLAY_NAME_INSET,
                   },
-                  isFromSelf ? a.self_end : a.self_start,
-                  isFromSelf
-                    ? {borderBottomRightRadius: needsTail ? 2 : 17}
-                    : {borderBottomLeftRadius: needsTail ? 2 : 17},
-                ]
-              }>
-              <RichText
-                value={rt}
-                style={[a.text_md, isFromSelf && {color: t.palette.white}]}
-                interactiveStyle={a.underline}
-                enableTags
-                emojiMultiplier={3}
-                shouldProxyLinks={true}
-              />
-            </View>
-          )}
-
-          {IS_NATIVE && appliedReactions}
-        </ActionsWrapper>
-
-        {!IS_NATIVE && appliedReactions}
-
-        {isLastInGroup && (
+                ]}>
+                {displayName}
+              </Text>
+            ) : null}
+            <ActionsWrapper isFromSelf={isFromSelf} message={message}>
+              {rt.text.length > 0 && (
+                <View
+                  style={[
+                    !isFromSelf && a.ml_sm,
+                    ...(isOnlyEmoji(message.text)
+                      ? []
+                      : [
+                          a.rounded_md,
+                          a.rounded_xl,
+                          a.py_sm,
+                          a.px_md,
+                          {
+                            marginTop: isFirstInCluster
+                              ? 0
+                              : CLUSTERED_MESSAGE_GAP,
+                            backgroundColor: isFromSelf
+                              ? isPending
+                                ? pendingColor
+                                : t.palette.primary_500
+                              : t.palette.contrast_50,
+                          },
+                          isFromSelf ? a.self_end : a.self_start,
+                          isFromSelf
+                            ? {
+                                borderBottomRightRadius:
+                                  squaredBottomCorner || hasEmbedAndText
+                                    ? SQUARED_BORDER_RADIUS
+                                    : BORDER_RADIUS,
+                                borderTopRightRadius: squaredTopCorner
+                                  ? SQUARED_BORDER_RADIUS
+                                  : BORDER_RADIUS,
+                              }
+                            : {
+                                borderBottomLeftRadius:
+                                  squaredBottomCorner || hasEmbedAndText
+                                    ? SQUARED_BORDER_RADIUS
+                                    : BORDER_RADIUS,
+                                borderTopLeftRadius: squaredTopCorner
+                                  ? SQUARED_BORDER_RADIUS
+                                  : BORDER_RADIUS,
+                              },
+                        ]),
+                  ]}>
+                  <RichText
+                    value={rt}
+                    style={[a.text_md, isFromSelf && {color: t.palette.white}]}
+                    interactiveStyle={a.underline}
+                    enableTags
+                    emojiMultiplier={3}
+                    shouldProxyLinks={true}
+                  />
+                </View>
+              )}
+              {AppBskyEmbedRecord.isView(message.embed) && (
+                <MessageItemEmbed
+                  embed={message.embed}
+                  isFromSelf={isFromSelf}
+                  squaredBottomCorner={squaredBottomCorner}
+                  squaredTopCorner={squaredTopCorner || hasEmbedAndText}
+                />
+              )}
+            </ActionsWrapper>
+          </View>
+        </View>
+        {appliedReactions}
+        {isLastInCluster && (
           <MessageItemMetadata
             item={item}
-            style={isFromSelf ? a.text_right : a.text_left}
+            style={[isFromSelf ? a.text_right : a.text_left]}
           />
         )}
       </View>
@@ -244,8 +415,7 @@ let MessageItemMetadata = ({
   style: StyleProp<TextStyle>
 }): React.ReactNode => {
   const t = useTheme()
-  const {_} = useLingui()
-  const {message} = item
+  const {t: l} = useLingui()
 
   const handleRetry = useCallback(
     (e: GestureResponderEvent) => {
@@ -258,75 +428,60 @@ let MessageItemMetadata = ({
     [item],
   )
 
-  const relativeTimestamp = useCallback(
-    (i18n: I18n, timestamp: string) => {
-      const date = new Date(timestamp)
-      const now = new Date()
+  const errorColor = t.palette.negative_400
 
-      const time = i18n.date(date, {
-        hour: 'numeric',
-        minute: 'numeric',
-      })
-
-      const diff = now.getTime() - date.getTime()
-
-      // if under 30 seconds
-      if (diff < 1000 * 30) {
-        return _(msg`Now`)
-      }
-
-      return time
-    },
-    [_],
-  )
-
-  return (
-    <Text
-      style={[
-        a.text_xs,
-        a.mt_2xs,
-        a.mb_lg,
-        t.atoms.text_contrast_medium,
-        style,
-      ]}>
-      <TimeElapsed timestamp={message.sentAt} timeToString={relativeTimestamp}>
-        {({timeElapsed}) => (
-          <Text style={[a.text_xs, t.atoms.text_contrast_medium]}>
-            {timeElapsed}
-          </Text>
-        )}
-      </TimeElapsed>
-
-      {item.type === 'pending-message' && item.failed && (
-        <>
-          {' '}
-          &middot;{' '}
+  switch (item.type) {
+    case 'pending-message':
+      return item.failed ? (
+        <Text
+          style={[
+            a.text_xs,
+            a.my_2xs,
+            {
+              color: errorColor,
+            },
+            style,
+          ]}>
           <Text
             style={[
               a.text_xs,
               {
-                color: t.palette.negative_400,
+                color: errorColor,
               },
             ]}>
-            {_(msg`Failed to send`)}
+            {l`Message failed to send.`}
           </Text>
           {item.retry && (
             <>
               {' '}
-              &middot;{' '}
               <InlineLinkText
-                label={_(msg`Click to retry failed message`)}
+                label={l`Click to retry failed message`}
                 to="#"
                 onPress={handleRetry}
-                style={[a.text_xs]}>
-                {_(msg`Retry`)}
+                style={[
+                  a.text_xs,
+                  {
+                    color: errorColor,
+                  },
+                ]}>
+                {l`Tap to retry`}
               </InlineLinkText>
+              .
             </>
           )}
-        </>
-      )}
-    </Text>
-  )
+        </Text>
+      ) : (
+        <Text
+          style={[
+            a.text_xs,
+            a.my_2xs,
+            style,
+            t.atoms.text_contrast_high,
+          ]}>{l`Sending…`}</Text>
+      )
+    default:
+      return null
+  }
 }
 MessageItemMetadata = memo(MessageItemMetadata)
 export {MessageItemMetadata}
diff --git a/src/components/dms/MessageItemEmbed.tsx b/src/components/dms/MessageItemEmbed.tsx
index 67f07dd4fc..ba48b6e123 100644
--- a/src/components/dms/MessageItemEmbed.tsx
+++ b/src/components/dms/MessageItemEmbed.tsx
@@ -2,14 +2,24 @@ import {memo} from 'react'
 import {useWindowDimensions, View} from 'react-native'
 import {type $Typed, type AppBskyEmbedRecord} from '@atproto/api'
 
-import {atoms as a, native, tokens, useTheme, web} from '#/alf'
+import {atoms as a, native, useTheme, web} from '#/alf'
 import {Embed, PostEmbedViewContext} from '#/components/Post/Embed'
 import {MessageContextProvider} from './MessageContext'
 
+const CLUSTERED_MESSAGE_GAP = 2
+const BORDER_RADIUS = 20
+const SQUARED_BORDER_RADIUS = 4
+
 let MessageItemEmbed = ({
   embed,
+  isFromSelf,
+  squaredTopCorner,
+  squaredBottomCorner,
 }: {
   embed: $Typed<AppBskyEmbedRecord.View>
+  isFromSelf: boolean
+  squaredTopCorner: boolean
+  squaredBottomCorner: boolean
 }): React.ReactNode => {
   const t = useTheme()
   const screen = useWindowDimensions()
@@ -18,7 +28,7 @@ let MessageItemEmbed = ({
     <MessageContextProvider>
       <View
         style={[
-          a.my_xs,
+          isFromSelf ? a.mr_sm : a.ml_sm,
           t.atoms.bg,
           a.rounded_md,
           native({
@@ -30,12 +40,38 @@ let MessageItemEmbed = ({
             minWidth: 280,
             maxWidth: 360,
           }),
+          {
+            marginTop: CLUSTERED_MESSAGE_GAP,
+          },
         ]}>
-        <View style={{marginTop: tokens.space.sm * -1}}>
+        <View style={{marginTop: -8}}>
           <Embed
             embed={embed}
             allowNestedQuotes
             viewContext={PostEmbedViewContext.Feed}
+            style={[
+              a.rounded_xl,
+              a.border_0,
+              isFromSelf
+                ? {
+                    backgroundColor: t.palette.primary_50,
+                    borderBottomRightRadius: squaredBottomCorner
+                      ? SQUARED_BORDER_RADIUS
+                      : BORDER_RADIUS,
+                    borderTopRightRadius: squaredTopCorner
+                      ? SQUARED_BORDER_RADIUS
+                      : BORDER_RADIUS,
+                  }
+                : {
+                    backgroundColor: t.palette.contrast_50,
+                    borderBottomLeftRadius: squaredBottomCorner
+                      ? SQUARED_BORDER_RADIUS
+                      : BORDER_RADIUS,
+                    borderTopLeftRadius: squaredTopCorner
+                      ? SQUARED_BORDER_RADIUS
+                      : BORDER_RADIUS,
+                  },
+            ]}
           />
         </View>
       </View>
diff --git a/src/components/dms/MessageItemEmbed_DEPRECATED.tsx b/src/components/dms/MessageItemEmbed_DEPRECATED.tsx
new file mode 100644
index 0000000000..a531c990c0
--- /dev/null
+++ b/src/components/dms/MessageItemEmbed_DEPRECATED.tsx
@@ -0,0 +1,49 @@
+import {memo} from 'react'
+import {useWindowDimensions, View} from 'react-native'
+import {type $Typed, type AppBskyEmbedRecord} from '@atproto/api'
+
+import {atoms as a, native, tokens, useTheme, web} from '#/alf'
+import {Embed, PostEmbedViewContext} from '#/components/Post/Embed'
+import {MessageContextProvider} from './MessageContext'
+
+/**
+ * @deprecated
+ */
+let MessageItemEmbed = ({
+  embed,
+}: {
+  embed: $Typed<AppBskyEmbedRecord.View>
+}): React.ReactNode => {
+  const t = useTheme()
+  const screen = useWindowDimensions()
+
+  return (
+    <MessageContextProvider>
+      <View
+        style={[
+          a.my_xs,
+          t.atoms.bg,
+          a.rounded_md,
+          native({
+            flexBasis: 0,
+            width: Math.min(screen.width, 600) / 1.4,
+          }),
+          web({
+            width: '100%',
+            minWidth: 280,
+            maxWidth: 360,
+          }),
+        ]}>
+        <View style={{marginTop: tokens.space.sm * -1}}>
+          <Embed
+            embed={embed}
+            allowNestedQuotes
+            viewContext={PostEmbedViewContext.Feed}
+          />
+        </View>
+      </View>
+    </MessageContextProvider>
+  )
+}
+MessageItemEmbed = memo(MessageItemEmbed)
+export {MessageItemEmbed}
diff --git a/src/components/dms/MessageItem_DEPRECATED.tsx b/src/components/dms/MessageItem_DEPRECATED.tsx
new file mode 100644
index 0000000000..efec8eb92c
--- /dev/null
+++ b/src/components/dms/MessageItem_DEPRECATED.tsx
@@ -0,0 +1,335 @@
+import {memo, useCallback, useMemo} from 'react'
+import {
+  type GestureResponderEvent,
+  type StyleProp,
+  type TextStyle,
+  View,
+} from 'react-native'
+import Animated, {
+  LayoutAnimationConfig,
+  LinearTransition,
+  ZoomIn,
+  ZoomOut,
+} from 'react-native-reanimated'
+import {
+  AppBskyEmbedRecord,
+  ChatBskyConvoDefs,
+  RichText as RichTextAPI,
+} from '@atproto/api'
+import {type I18n} from '@lingui/core'
+import {msg} from '@lingui/core/macro'
+import {useLingui} from '@lingui/react'
+
+import {sanitizeDisplayName} from '#/lib/strings/display-names'
+import {useConvoActive} from '#/state/messages/convo'
+import {type ConvoItem} from '#/state/messages/convo/types'
+import {useSession} from '#/state/session'
+import {TimeElapsed} from '#/view/com/util/TimeElapsed'
+import {atoms as a, native, useTheme} from '#/alf'
+import {isOnlyEmoji} from '#/alf/typography'
+import {ActionsWrapper} from '#/components/dms/ActionsWrapper'
+import {InlineLinkText} from '#/components/Link'
+import {RichText} from '#/components/RichText'
+import {Text} from '#/components/Typography'
+import {IS_NATIVE} from '#/env'
+import {DateDivider as DateDividerDeprecated} from './DateDivider_DEPRECATED'
+import {MessageItemEmbed as MessageItemEmbedDeprecated} from './MessageItemEmbed_DEPRECATED'
+import {localDateString} from './util'
+
+/**
+ * @deprecated
+ */
+let MessageItem = ({
+  item,
+}: {
+  item: ConvoItem & {type: 'message' | 'pending-message'}
+}): React.ReactNode => {
+  const t = useTheme()
+  const {currentAccount} = useSession()
+  const {_} = useLingui()
+  const {convo} = useConvoActive()
+
+  const {message, nextMessage, prevMessage} = item
+  const isPending = item.type === 'pending-message'
+
+  const isFromSelf = message.sender?.did === currentAccount?.did
+
+  const nextIsMessage = ChatBskyConvoDefs.isMessageView(nextMessage)
+
+  const isNextFromSelf =
+    nextIsMessage && nextMessage.sender?.did === currentAccount?.did
+
+  const isNextFromSameSender = isNextFromSelf === isFromSelf
+
+  const isNewDay = useMemo(() => {
+    if (!prevMessage) return true
+
+    const thisDate = new Date(message.sentAt)
+    const prevDate = new Date(prevMessage.sentAt)
+
+    return localDateString(thisDate) !== localDateString(prevDate)
+  }, [message, prevMessage])
+
+  const isLastMessageOfDay = useMemo(() => {
+    if (!nextMessage || !nextIsMessage) return true
+
+    const thisDate = new Date(message.sentAt)
+    const prevDate = new Date(nextMessage.sentAt)
+
+    return localDateString(thisDate) !== localDateString(prevDate)
+  }, [message.sentAt, nextIsMessage, nextMessage])
+
+  const needsTail = isLastMessageOfDay || !isNextFromSameSender
+
+  const isLastInGroup = useMemo(() => {
+    // if this message is pending, it means the next message is pending too
+    if (isPending && nextMessage) {
+      return false
+    }
+
+    // or, if there's a 5 minute gap between this message and the next
+    if (ChatBskyConvoDefs.isMessageView(nextMessage)) {
+      const thisDate = new Date(message.sentAt)
+      const nextDate = new Date(nextMessage.sentAt)
+
+      const diff = nextDate.getTime() - thisDate.getTime()
+
+      // 5 minutes
+      return diff > 5 * 60 * 1000
+    }
+
+    return true
+  }, [message, nextMessage, isPending])
+
+  const pendingColor = t.palette.primary_200
+
+  const rt = useMemo(() => {
+    return new RichTextAPI({text: message.text, facets: message.facets})
+  }, [message.text, message.facets])
+
+  const appliedReactions = (
+    <LayoutAnimationConfig skipEntering skipExiting>
+      {message.reactions && message.reactions.length > 0 && (
+        <View
+          style={[isFromSelf ? a.align_end : a.align_start, a.px_sm, a.pb_2xs]}>
+          <View
+            style={[
+              a.flex_row,
+              a.gap_2xs,
+              a.py_xs,
+              a.px_xs,
+              a.justify_center,
+              isFromSelf ? a.justify_end : a.justify_start,
+              a.flex_wrap,
+              a.pb_xs,
+              t.atoms.bg_contrast_25,
+              a.border,
+              t.atoms.border_contrast_low,
+              a.rounded_lg,
+              t.atoms.shadow_sm,
+              {
+                // vibe coded number
+                transform: [{translateY: -11}],
+              },
+            ]}>
+            {message.reactions.map((reaction, _i, reactions) => {
+              let label
+              if (reaction.sender.did === currentAccount?.did) {
+                label = _(msg`You reacted ${reaction.value}`)
+              } else {
+                const senderDid = reaction.sender.did
+                const sender = convo.members.find(
+                  member => member.did === senderDid,
+                )
+                if (sender) {
+                  label = _(
+                    msg`${sanitizeDisplayName(
+                      sender.displayName || sender.handle,
+                    )} reacted ${reaction.value}`,
+                  )
+                } else {
+                  label = _(msg`Someone reacted ${reaction.value}`)
+                }
+              }
+              return (
+                <Animated.View
+                  entering={native(ZoomIn.springify(200).delay(400))}
+                  exiting={reactions.length > 1 && native(ZoomOut.delay(200))}
+                  layout={native(LinearTransition.delay(300))}
+                  key={reaction.sender.did + reaction.value}
+                  style={[a.p_2xs]}
+                  accessible={true}
+                  accessibilityLabel={label}
+                  accessibilityHint={_(
+                    msg`Double tap or long press the message to add a reaction`,
+                  )}>
+                  <Text emoji style={[a.text_sm]}>
+                    {reaction.value}
+                  </Text>
+                </Animated.View>
+              )
+            })}
+          </View>
+        </View>
+      )}
+    </LayoutAnimationConfig>
+  )
+
+  return (
+    <>
+      {isNewDay && <DateDividerDeprecated date={message.sentAt} />}
+      <View
+        style={[
+          isFromSelf ? a.mr_md : a.ml_md,
+          nextIsMessage && !isNextFromSameSender && a.mb_md,
+        ]}>
+        <ActionsWrapper isFromSelf={isFromSelf} message={message}>
+          {AppBskyEmbedRecord.isView(message.embed) && (
+            <MessageItemEmbedDeprecated embed={message.embed} />
+          )}
+          {rt.text.length > 0 && (
+            <View
+              style={
+                !isOnlyEmoji(message.text) && [
+                  a.py_sm,
+                  a.my_2xs,
+                  a.rounded_md,
+                  {
+                    paddingLeft: 14,
+                    paddingRight: 14,
+                    backgroundColor: isFromSelf
+                      ? isPending
+                        ? pendingColor
+                        : t.palette.primary_500
+                      : t.palette.contrast_50,
+                    borderRadius: 17,
+                  },
+                  isFromSelf ? a.self_end : a.self_start,
+                  isFromSelf
+                    ? {borderBottomRightRadius: needsTail ? 2 : 17}
+                    : {borderBottomLeftRadius: needsTail ? 2 : 17},
+                ]
+              }>
+              <RichText
+                value={rt}
+                style={[a.text_md, isFromSelf && {color: t.palette.white}]}
+                interactiveStyle={a.underline}
+                enableTags
+                emojiMultiplier={3}
+                shouldProxyLinks={true}
+              />
+            </View>
+          )}
+
+          {IS_NATIVE && appliedReactions}
+        </ActionsWrapper>
+
+        {!IS_NATIVE && appliedReactions}
+
+        {isLastInGroup && (
+          <MessageItemMetadata
+            item={item}
+            style={isFromSelf ? a.text_right : a.text_left}
+          />
+        )}
+      </View>
+    </>
+  )
+}
+MessageItem = memo(MessageItem)
+export {MessageItem}
+
+let MessageItemMetadata = ({
+  item,
+  style,
+}: {
+  item: ConvoItem & {type: 'message' | 'pending-message'}
+  style: StyleProp<TextStyle>
+}): React.ReactNode => {
+  const t = useTheme()
+  const {_} = useLingui()
+  const {message} = item
+
+  const handleRetry = useCallback(
+    (e: GestureResponderEvent) => {
+      if (item.type === 'pending-message' && item.retry) {
+        e.preventDefault()
+        item.retry()
+        return false
+      }
+    },
+    [item],
+  )
+
+  const relativeTimestamp = useCallback(
+    (i18n: I18n, timestamp: string) => {
+      const date = new Date(timestamp)
+      const now = new Date()
+
+      const time = i18n.date(date, {
+        hour: 'numeric',
+        minute: 'numeric',
+      })
+
+      const diff = now.getTime() - date.getTime()
+
+      // if under 30 seconds
+      if (diff < 1000 * 30) {
+        return _(msg`Now`)
+      }
+
+      return time
+    },
+    [_],
+  )
+
+  return (
+    <Text
+      style={[
+        a.text_xs,
+        a.mt_2xs,
+        a.mb_lg,
+        t.atoms.text_contrast_medium,
+        style,
+      ]}>
+      <TimeElapsed timestamp={message.sentAt} timeToString={relativeTimestamp}>
+        {({timeElapsed}) => (
+          <Text style={[a.text_xs, t.atoms.text_contrast_medium]}>
+            {timeElapsed}
+          </Text>
+        )}
+      </TimeElapsed>
+
+      {item.type === 'pending-message' && item.failed && (
+        <>
+          {' '}
+          &middot;{' '}
+          <Text
+            style={[
+              a.text_xs,
+              {
+                color: t.palette.negative_400,
+              },
+            ]}>
+            {_(msg`Failed to send`)}
+          </Text>
+          {item.retry && (
+            <>
+              {' '}
+              &middot;{' '}
+              <InlineLinkText
+                label={_(msg`Click to retry failed message`)}
+                to="#"
+                onPress={handleRetry}
+                style={[a.text_xs]}>
+                {_(msg`Retry`)}
+              </InlineLinkText>
+            </>
+          )}
+        </>
+      )}
+    </Text>
+  )
+}
+MessageItemMetadata = memo(MessageItemMetadata)
+export {MessageItemMetadata}
diff --git a/src/screens/Messages/components/MessageInput.tsx b/src/screens/Messages/components/MessageInput.tsx
index 643c0c86a6..e2bf735713 100644
--- a/src/screens/Messages/components/MessageInput.tsx
+++ b/src/screens/Messages/components/MessageInput.tsx
@@ -15,8 +15,7 @@ import Animated, {
 } from 'react-native-reanimated'
 import {useSafeAreaInsets} from 'react-native-safe-area-context'
 import {GlassContainer} from 'expo-glass-effect'
-import {msg} from '@lingui/core/macro'
-import {useLingui} from '@lingui/react'
+import {useLingui} from '@lingui/react/macro'
 import {countGraphemes} from 'unicode-segmenter/grapheme'
 
 import {HITSLOP_10, MAX_DM_GRAPHEME_LENGTH} from '#/lib/constants'
@@ -47,13 +46,13 @@ export function MessageInput({
   children,
 }: {
   textInputId?: string
-  onSendMessage: (message: string) => void
+  onSendMessage: (message: string) => Promise<void> | void
   hasEmbed: boolean
   setEmbed: (embedUrl: string | undefined) => void
   children?: React.ReactNode
   openEmojiPicker?: (pos: EmojiPickerPosition) => void
 }) {
-  const {_} = useLingui()
+  const {t: l} = useLingui()
   const t = useTheme()
   const playHaptic = useHaptics()
   const {getDraft, clearDraft} = useMessageDraft()
@@ -82,13 +81,13 @@ export function MessageInput({
       return
     }
     if (countGraphemes(message) > MAX_DM_GRAPHEME_LENGTH) {
-      Toast.show(_(msg`Message is too long`), {
+      Toast.show(l`Message is too long`, {
         type: 'error',
       })
       return
     }
     clearDraft()
-    onSendMessage(message)
+    void onSendMessage(message)
     playHaptic()
     setEmbed(undefined)
     setMessage('')
@@ -111,7 +110,7 @@ export function MessageInput({
     playHaptic,
     setEmbed,
     inputRef,
-    _,
+    l,
   ])
 
   useFocusedInputHandler(
@@ -169,9 +168,9 @@ export function MessageInput({
           fallbackStyle={[t.atoms.bg_contrast_50]}>
           <AnimatedTextInput
             nativeID={textInputId}
-            accessibilityLabel={_(msg`Message input field`)}
-            accessibilityHint={_(msg`Type your message here`)}
-            placeholder={_(msg`Message`)}
+            accessibilityLabel={l`Message input field`}
+            accessibilityHint={l`Type your message here`}
+            placeholder={l`Message`}
             placeholderTextColor={t.palette.contrast_500}
             value={message}
             onChange={evt => {
@@ -225,7 +224,7 @@ export function MessageInput({
           }}>
           <Pressable
             accessibilityRole="button"
-            accessibilityLabel={_(msg`Send message`)}
+            accessibilityLabel={l`Send message`}
             accessibilityHint=""
             hitSlop={HITSLOP_10}
             style={[
diff --git a/src/screens/Messages/components/MessageInput.web.tsx b/src/screens/Messages/components/MessageInput.web.tsx
index 5113027f06..5e71fb2ef0 100644
--- a/src/screens/Messages/components/MessageInput.web.tsx
+++ b/src/screens/Messages/components/MessageInput.web.tsx
@@ -1,7 +1,6 @@
 import {useCallback, useEffect, useRef, useState} from 'react'
 import {Pressable, View} from 'react-native'
-import {msg} from '@lingui/core/macro'
-import {useLingui} from '@lingui/react'
+import {useLingui} from '@lingui/react/macro'
 import {flushSync} from 'react-dom'
 import TextareaAutosize from 'react-textarea-autosize'
 import {countGraphemes} from 'unicode-segmenter/grapheme'
@@ -40,7 +39,7 @@ export function MessageInput({
   openEmojiPicker?: (pos: EmojiPickerPosition) => void
 }) {
   const {isMobile} = useWebMediaQueries()
-  const {_} = useLingui()
+  const {t: l} = useLingui()
   const t = useTheme()
   const {getDraft, clearDraft} = useMessageDraft()
   const [message, setMessage] = useState(getDraft)
@@ -57,7 +56,7 @@ export function MessageInput({
       return
     }
     if (countGraphemes(message) > MAX_DM_GRAPHEME_LENGTH) {
-      Toast.show(_(msg`Message is too long`), {
+      Toast.show(l`Message is too long`, {
         type: 'error',
       })
       return
@@ -66,7 +65,7 @@ export function MessageInput({
     onSendMessage(message)
     setMessage('')
     setEmbed(undefined)
-  }, [message, onSendMessage, _, clearDraft, hasEmbed, setEmbed])
+  }, [message, onSendMessage, l, clearDraft, hasEmbed, setEmbed])
 
   const onKeyDown = useCallback(
     (e: React.KeyboardEvent<HTMLTextAreaElement>) => {
@@ -177,7 +176,7 @@ export function MessageInput({
               width: 30,
             },
           ]}
-          label={_(msg`Open emoji picker`)}>
+          label={l`Open emoji picker`}>
           {state => (
             <View
               style={[
@@ -210,7 +209,7 @@ export function MessageInput({
             },
           ])}
           maxRows={12}
-          placeholder={_(msg`Write a message`)}
+          placeholder={l`Message`}
           defaultValue=""
           value={message}
           dirName="ltr"
@@ -231,7 +230,7 @@ export function MessageInput({
         />
         <Pressable
           accessibilityRole="button"
-          accessibilityLabel={_(msg`Send message`)}
+          accessibilityLabel={l`Send message`}
           accessibilityHint=""
           style={[
             a.rounded_full,
diff --git a/src/screens/Messages/components/MessageListError.tsx b/src/screens/Messages/components/MessageListError.tsx
index c4be6ca2e8..3b424cb395 100644
--- a/src/screens/Messages/components/MessageListError.tsx
+++ b/src/screens/Messages/components/MessageListError.tsx
@@ -1,34 +1,33 @@
 import {useMemo} from 'react'
 import {View} from 'react-native'
-import {msg} from '@lingui/core/macro'
-import {useLingui} from '@lingui/react'
+import {useLingui} from '@lingui/react/macro'
 
 import {type ConvoItem, ConvoItemError} from '#/state/messages/convo/types'
 import {atoms as a, useTheme} from '#/alf'
 import {CircleInfo_Stroke2_Corner0_Rounded as CircleInfo} from '#/components/icons/CircleInfo'
-import {InlineLinkText} from '#/components/Link'
+import {createStaticClick, InlineLinkText} from '#/components/Link'
 import {Text} from '#/components/Typography'
 
 export function MessageListError({item}: {item: ConvoItem & {type: 'error'}}) {
   const t = useTheme()
-  const {_} = useLingui()
+  const {t: l} = useLingui()
   const {description, help, cta} = useMemo(() => {
     return {
       [ConvoItemError.FirehoseFailed]: {
-        description: _(msg`This chat was disconnected`),
-        help: _(msg`Press to attempt reconnection`),
-        cta: _(msg`Reconnect`),
+        description: l`This chat was disconnected`,
+        help: l`Press to attempt reconnection`,
+        cta: l`Reconnect`,
       },
       [ConvoItemError.HistoryFailed]: {
-        description: _(msg`Failed to load past messages`),
-        help: _(msg`Press to retry`),
-        cta: _(msg`Retry`),
+        description: l`Failed to load past messages`,
+        help: l`Press to retry`,
+        cta: l`Retry`,
       },
     }[item.code]
-  }, [_, item.code])
+  }, [l, item.code])
 
   return (
-    <View style={[a.py_md, a.w_full, a.flex_row, a.justify_center]}>
+    <View style={[a.my_md, a.w_full, a.flex_row, a.justify_center]}>
       <View
         style={[
           a.flex_1,
@@ -41,18 +40,18 @@ export function MessageListError({item}: {item: ConvoItem & {type: 'error'}}) {
         <CircleInfo size="sm" fill={t.palette.negative_400} />
 
         <Text style={[a.leading_snug, t.atoms.text_contrast_medium]}>
-          {description} &middot;{' '}
+          {description}
           {item.retry && (
-            <InlineLinkText
-              to="#"
-              label={help}
-              onPress={e => {
-                e.preventDefault()
-                item.retry?.()
-                return false
-              }}>
-              {cta}
-            </InlineLinkText>
+            <>
+              &middot;{' '}
+              <InlineLinkText
+                label={help}
+                {...createStaticClick(() => {
+                  item.retry?.()
+                })}>
+                {cta}
+              </InlineLinkText>
+            </>
           )}
         </Text>
       </View>
diff --git a/src/screens/Messages/components/MessageListError_DEPRECATED.tsx b/src/screens/Messages/components/MessageListError_DEPRECATED.tsx
new file mode 100644
index 0000000000..0e84fb51d4
--- /dev/null
+++ b/src/screens/Messages/components/MessageListError_DEPRECATED.tsx
@@ -0,0 +1,64 @@
+import {useMemo} from 'react'
+import {View} from 'react-native'
+import {msg} from '@lingui/core/macro'
+import {useLingui} from '@lingui/react'
+
+import {type ConvoItem, ConvoItemError} from '#/state/messages/convo/types'
+import {atoms as a, useTheme} from '#/alf'
+import {CircleInfo_Stroke2_Corner0_Rounded as CircleInfo} from '#/components/icons/CircleInfo'
+import {InlineLinkText} from '#/components/Link'
+import {Text} from '#/components/Typography'
+
+/**
+ * @deprecated
+ */
+export function MessageListError({item}: {item: ConvoItem & {type: 'error'}}) {
+  const t = useTheme()
+  const {_} = useLingui()
+  const {description, help, cta} = useMemo(() => {
+    return {
+      [ConvoItemError.FirehoseFailed]: {
+        description: _(msg`This chat was disconnected`),
+        help: _(msg`Press to attempt reconnection`),
+        cta: _(msg`Reconnect`),
+      },
+      [ConvoItemError.HistoryFailed]: {
+        description: _(msg`Failed to load past messages`),
+        help: _(msg`Press to retry`),
+        cta: _(msg`Retry`),
+      },
+    }[item.code]
+  }, [_, item.code])
+
+  return (
+    <View style={[a.py_md, a.w_full, a.flex_row, a.justify_center]}>
+      <View
+        style={[
+          a.flex_1,
+          a.flex_row,
+          a.align_center,
+          a.justify_center,
+          a.gap_sm,
+          {maxWidth: 400},
+        ]}>
+        <CircleInfo size="sm" fill={t.palette.negative_400} />
+
+        <Text style={[a.leading_snug, t.atoms.text_contrast_medium]}>
+          {description} &middot;{' '}
+          {item.retry && (
+            <InlineLinkText
+              to="#"
+              label={help}
+              onPress={e => {
+                e.preventDefault()
+                item.retry?.()
+                return false
+              }}>
+              {cta}
+            </InlineLinkText>
+          )}
+        </Text>
+      </View>
+    </View>
+  )
+}
diff --git a/src/screens/Messages/components/MessagesList.tsx b/src/screens/Messages/components/MessagesList.tsx
index eda3c593d9..617582d824 100644
--- a/src/screens/Messages/components/MessagesList.tsx
+++ b/src/screens/Messages/components/MessagesList.tsx
@@ -5,7 +5,7 @@ import {
   type KeyboardChatScrollViewProps,
   KeyboardGestureArea,
 } from 'react-native-keyboard-controller'
-import Animated, {
+import {
   runOnJS,
   type ScrollEvent,
   type SharedValue,
@@ -51,9 +51,11 @@ import {ChatDisabled} from '#/screens/Messages/components/ChatDisabled'
 import {MessageComposer} from '#/screens/Messages/components/MessageComposer'
 import {MessageInput} from '#/screens/Messages/components/MessageInput'
 import {MessageListError} from '#/screens/Messages/components/MessageListError'
+import {MessageListError as MessageListErrorDeprecated} from '#/screens/Messages/components/MessageListError_DEPRECATED'
 import {atoms as a, platform, tokens, useTheme, web} from '#/alf'
 import {ChatEmptyPill} from '#/components/dms/ChatEmptyPill'
 import {MessageItem} from '#/components/dms/MessageItem'
+import {MessageItem as MessageItemDeprecated} from '#/components/dms/MessageItem_DEPRECATED'
 import {NewMessagesPill} from '#/components/dms/NewMessagesPill'
 import {Loader} from '#/components/Loader'
 import {Text} from '#/components/Typography'
@@ -77,18 +79,6 @@ function MaybeLoader({isLoading}: {isLoading: boolean}) {
   )
 }
 
-function renderItem({item}: {item: ConvoItem}) {
-  if (item.type === 'message' || item.type === 'pending-message') {
-    return <MessageItem item={item} />
-  } else if (item.type === 'deleted-message') {
-    return <Text>Deleted message</Text>
-  } else if (item.type === 'error') {
-    return <MessageListError item={item} />
-  }
-
-  return null
-}
-
 function keyExtractor(item: ConvoItem) {
   return item.key
 }
@@ -117,6 +107,8 @@ export function MessagesList({
   const {embedUri, setEmbed} = useMessageEmbed()
   const t = useTheme()
 
+  const isGroupChatEnabled = ax.features.enabled(ax.features.GroupChatsEnable)
+
   const textInputId = 'chat-input-' + useId()
   const flatListRef = useAnimatedRef<ListMethods>()
 
@@ -369,6 +361,32 @@ export function MessagesList({
     setEmojiPickerState({isOpen: true, pos})
   }, [])
 
+  const renderItem = ({item}: {item: ConvoItem}) => {
+    if (item.type === 'message' || item.type === 'pending-message') {
+      return isGroupChatEnabled ? (
+        <MessageItem
+          item={item}
+          profile={convoState.convo.members.find(
+            member => member.did === item.message.sender.did,
+          )}
+          isGroupChat={convoState.convo.kind === 'group'}
+        />
+      ) : (
+        <MessageItemDeprecated item={item} />
+      )
+    } else if (item.type === 'deleted-message') {
+      return <Text>Deleted message</Text>
+    } else if (item.type === 'error') {
+      return isGroupChatEnabled ? (
+        <MessageListError item={item} />
+      ) : (
+        <MessageListErrorDeprecated item={item} />
+      )
+    }
+
+    return null
+  }
+
   const renderScrollComponent = useCallback(
     (props: ScrollViewProps) => (
       <ChatScrollComponent {...props} inputHeight={inputHeightUI} />
@@ -411,9 +429,18 @@ export function MessagesList({
             }
             // native only (prop is not supported on web)
             renderScrollComponent={renderScrollComponent}
-            // pushes up the content under the input on web (renderScrollComponent handles it on native)
+            contentContainerStyle={{
+              paddingBottom: platform({
+                // ios is slightly larger as the input has no top padding
+                ios: tokens.space.lg,
+                android: tokens.space.md,
+                web: 0, // web uses ListFooterComponent instead for scroll reasons
+              }),
+            }}
+            // adds extra space underneath the absolutely positioned input on web
+            // as renderScrollComponent isn't available here (luckily we don't need the fancy behaviour)
             ListFooterComponent={web(
-              <WebInputSpacer inputHeight={inputHeightJS} />,
+              <View style={{height: tokens.space.md + inputHeightJS}} />,
             )}
             style={web({
               scrollbarWidth: 'thin',
@@ -518,12 +545,6 @@ function ChatScrollComponent({
   )
 }
 
-function WebInputSpacer({inputHeight}: {inputHeight: number}) {
-  if (!IS_WEB) return null
-
-  return <Animated.View style={{height: inputHeight}} />
-}
-
 type FooterState = 'loading' | 'new-chat' | 'request' | 'standard'
 
 function getFooterState(
diff --git a/src/state/messages/convo/agent.ts b/src/state/messages/convo/agent.ts
index b6c8ee2f16..93726833f1 100644
--- a/src/state/messages/convo/agent.ts
+++ b/src/state/messages/convo/agent.ts
@@ -222,7 +222,7 @@ export class Convo {
         switch (action.event) {
           case ConvoDispatchEvent.Init: {
             this.status = ConvoStatus.Initializing
-            this.setup()
+            void this.setup()
             this.setupFirehose()
             this.requestPollInterval(ACTIVE_POLL_INTERVAL)
             break
@@ -234,12 +234,12 @@ export class Convo {
         switch (action.event) {
           case ConvoDispatchEvent.Ready: {
             this.status = ConvoStatus.Ready
-            this.fetchMessageHistory()
+            void this.fetchMessageHistory()
             break
           }
           case ConvoDispatchEvent.Background: {
             this.status = ConvoStatus.Backgrounded
-            this.fetchMessageHistory()
+            void this.fetchMessageHistory()
             this.requestPollInterval(BACKGROUND_POLL_INTERVAL)
             break
           }
@@ -258,7 +258,7 @@ export class Convo {
           }
           case ConvoDispatchEvent.Disable: {
             this.status = ConvoStatus.Disabled
-            this.fetchMessageHistory() // finish init
+            void this.fetchMessageHistory() // finish init
             this.cleanupFirehoseConnection?.()
             this.withdrawRequestedPollInterval()
             break
@@ -269,7 +269,7 @@ export class Convo {
       case ConvoStatus.Ready: {
         switch (action.event) {
           case ConvoDispatchEvent.Resume: {
-            this.refreshConvo()
+            void this.refreshConvo()
             this.requestPollInterval(ACTIVE_POLL_INTERVAL)
             break
           }
@@ -308,11 +308,11 @@ export class Convo {
             } else {
               if (this.convo) {
                 this.status = ConvoStatus.Ready
-                this.refreshConvo()
+                void this.refreshConvo()
                 this.maybeRecoverFromNetworkError()
               } else {
                 this.status = ConvoStatus.Initializing
-                this.setup()
+                void this.setup()
               }
               this.requestPollInterval(ACTIVE_POLL_INTERVAL)
             }
@@ -435,7 +435,7 @@ export class Convo {
       this.firehoseError = undefined
       this.commit()
     } else {
-      this.batchRetryPendingMessages()
+      void this.batchRetryPendingMessages()
     }
 
     if (this.fetchMessageHistoryError) {
@@ -487,7 +487,8 @@ export class Convo {
       } else {
         this.dispatch({event: ConvoDispatchEvent.Ready})
       }
-    } catch (e: any) {
+    } catch (err) {
+      const e = err as Error
       if (!isNetworkError(e) && !isErrorMaybeAppPasswordPermissions(e)) {
         logger.error('setup failed', {
           safeMessage: e.message,
@@ -557,11 +558,7 @@ export class Convo {
   async fetchConvo() {
     if (this.pendingFetchConvo) return this.pendingFetchConvo
 
-    this.pendingFetchConvo = new Promise<{
-      convo: ChatBskyConvoDefs.ConvoView
-      sender: ChatBskyActorDefs.ProfileViewBasic | undefined
-      recipients: ChatBskyActorDefs.ProfileViewBasic[]
-    }>(async (resolve, reject) => {
+    this.pendingFetchConvo = (async () => {
       try {
         const response = await networkRetry(2, () => {
           return this.agent.api.chat.bsky.convo.getConvo(
@@ -574,17 +571,15 @@ export class Convo {
 
         const convo = response.data.convo
 
-        resolve({
+        return {
           convo,
           sender: convo.members.find(m => m.did === this.senderUserDid),
           recipients: convo.members.filter(m => m.did !== this.senderUserDid),
-        })
-      } catch (e) {
-        reject(e)
+        }
       } finally {
         this.pendingFetchConvo = undefined
       }
-    })
+    })()
 
     return this.pendingFetchConvo
   }
@@ -596,7 +591,8 @@ export class Convo {
       this.convo = convo || this.convo
       this.sender = sender || this.sender
       this.recipients = recipients || this.recipients
-    } catch (e: any) {
+    } catch (err) {
+      const e = err as Error
       if (!isNetworkError(e) && !isErrorMaybeAppPasswordPermissions(e)) {
         logger.error(`failed to refresh convo`, {
           safeMessage: e.message,
@@ -664,7 +660,8 @@ export class Convo {
           this.pastMessages.set(message.id, message)
         }
       }
-    } catch (e: any) {
+    } catch (err) {
+      const e = err as Error
       if (!isNetworkError(e) && !isErrorMaybeAppPasswordPermissions(e)) {
         logger.error('failed to fetch message history', {
           safeMessage: e.message,
@@ -673,7 +670,7 @@ export class Convo {
 
       this.fetchMessageHistoryError = {
         retry: () => {
-          this.fetchMessageHistory()
+          void this.fetchMessageHistory()
         },
       }
     } finally {
@@ -716,7 +713,7 @@ export class Convo {
 
   onFirehoseConnect() {
     this.firehoseError = undefined
-    this.batchRetryPendingMessages()
+    void this.batchRetryPendingMessages()
     this.commit()
   }
 
@@ -761,8 +758,8 @@ export class Convo {
             /**
              * If this message is already in new messages, it was added by our
              * sending logic, and is based on client-ordering. When we receive
-             * the "commited" event from the log, we should replace this
-             * reference and re-insert in order to respect the order we receied
+             * the "committed" event from the log, we should replace this
+             * reference and re-insert in order to respect the order we received
              * from the log.
              */
             if (this.newMessages.has(ev.message.id)) {
@@ -836,7 +833,7 @@ export class Convo {
     this.commit()
 
     if (!this.isProcessingPendingMessages && !this.pendingMessageFailure) {
-      this.processPendingMessages()
+      void this.processPendingMessages()
     }
   }
 
@@ -912,7 +909,7 @@ export class Convo {
     }
   }
 
-  private handleSendMessageFailure(e: any) {
+  private handleSendMessageFailure(e: Error | XRPCError) {
     if (e instanceof XRPCError) {
       if (NETWORK_FAILURE_STATUSES.includes(e.status)) {
         this.pendingMessageFailure = 'recoverable'
@@ -1026,7 +1023,8 @@ export class Convo {
           {encoding: 'application/json', headers: DM_SERVICE_HEADERS},
         )
       })
-    } catch (e: any) {
+    } catch (err) {
+      const e = err as Error
       if (!isNetworkError(e) && !isErrorMaybeAppPasswordPermissions(e)) {
         logger.error(`failed to delete message`, {
           safeMessage: e.message,