diff --git a/frontend/apps/main/src/features/conversation/list/ConversationListItem.vue b/frontend/apps/main/src/features/conversation/list/ConversationListItem.vue
index cfa7b441..f4011c56 100644
--- a/frontend/apps/main/src/features/conversation/list/ConversationListItem.vue
+++ b/frontend/apps/main/src/features/conversation/list/ConversationListItem.vue
@@ -3,10 +3,11 @@
     <ContextMenuTrigger asChild>
       <router-link
         :to="conversationRoute"
-        class="group relative block px-3 py-3 transition-all duration-200 ease-in-out cursor-pointer hover:bg-accent/20 dark:hover:bg-accent/60"
+        class="group relative block px-3 py-3 transition-all duration-200 ease-in-out cursor-pointer"
         :class="{
-          'bg-accent/60': conversation.uuid === currentConversation?.uuid,
-          'bg-primary/5': isItemSelected && conversation.uuid !== currentConversation?.uuid
+          'bg-accent': isCurrent,
+          'bg-primary/5 hover:bg-primary/10': isItemSelected && !isCurrent,
+          'hover:bg-accent/40': !isCurrent && !isItemSelected
         }"
       >
         <div class="flex items-start gap-2">
@@ -51,9 +52,14 @@
               <!-- Contact name + inbox + time -->
               <div class="flex items-baseline justify-between gap-2">
                 <div class="flex items-baseline gap-1.5 min-w-0">
-                  <h3 class="text-sm font-semibold truncate text-foreground">
-                    {{ contactFullName }}
-                  </h3>
+                  <Tooltip>
+                    <TooltipTrigger asChild>
+                      <h3 class="text-sm font-semibold truncate text-foreground">
+                        {{ contactFullName }}
+                      </h3>
+                    </TooltipTrigger>
+                    <TooltipContent>{{ contactFullName }}</TooltipContent>
+                  </Tooltip>
                   <span class="text-xs text-muted-foreground truncate">
                     {{ conversation.inbox_name }}
                   </span>
@@ -154,6 +160,7 @@ import {
   ContextMenuTrigger
 } from '@shared-ui/components/ui/context-menu'
 import SlaBadge from '@main/features/sla/SlaBadge.vue'
+import { Tooltip, TooltipContent, TooltipTrigger } from '@shared-ui/components/ui/tooltip'
 import { Checkbox } from '@shared-ui/components/ui/checkbox'
 import { useConversationStore } from '@main/stores/conversation'
 import { useBulkActionPermissions } from '@/composables/useBulkActionPermissions'
@@ -235,6 +242,8 @@ const draftPreview = computed(() => {
   return text.length > 120 ? text.slice(0, 120) + '...' : text
 })
 
+const isCurrent = computed(() => props.conversation.uuid === props.currentConversation?.uuid)
+
 const isItemSelected = computed(() => {
   return conversationStore.isSelected(props.conversation.uuid)
 })
diff --git a/frontend/apps/main/src/features/conversation/message/MessageBubble.vue b/frontend/apps/main/src/features/conversation/message/MessageBubble.vue
index 3a4a66d7..562db8d8 100644
--- a/frontend/apps/main/src/features/conversation/message/MessageBubble.vue
+++ b/frontend/apps/main/src/features/conversation/message/MessageBubble.vue
@@ -1,7 +1,11 @@
 <template>
   <div class="flex flex-col text-left" :class="isOutgoing ? 'items-end' : 'items-start'">
     <!-- Sender Name -->
-    <div class="mb-1 flex items-center gap-1" :class="isOutgoing ? 'pr-[47px]' : 'pl-[47px]'">
+    <div
+      v-if="!groupWithPrev"
+      class="mb-1 flex items-center gap-1"
+      :class="isOutgoing ? 'pr-[47px]' : 'pl-[47px]'"
+    >
       <router-link
         v-if="!isOutgoing"
         :to="{ name: 'contact-detail', params: { id: message.author?.id } }"
@@ -24,18 +28,21 @@
     <!-- Message Bubble -->
     <div class="flex flex-row gap-2 w-full" :class="{ 'justify-end': isOutgoing }">
       <!-- Avatar (left for incoming) -->
-      <router-link
-        v-if="!isOutgoing"
-        :to="{ name: 'contact-detail', params: { id: message.author?.id } }"
-        class="flex-shrink-0"
-      >
-        <Avatar class="cursor-pointer w-8 h-8 hover:opacity-80 transition-opacity">
-          <AvatarImage :src="getAvatar" />
-          <AvatarFallback class="font-medium">
-            {{ avatarFallback }}
-          </AvatarFallback>
-        </Avatar>
-      </router-link>
+      <template v-if="!isOutgoing">
+        <router-link
+          v-if="!groupWithPrev"
+          :to="{ name: 'contact-detail', params: { id: message.author?.id } }"
+          class="flex-shrink-0"
+        >
+          <Avatar class="cursor-pointer w-8 h-8 hover:opacity-80 transition-opacity">
+            <AvatarImage :src="getAvatar" />
+            <AvatarFallback class="font-medium">
+              {{ avatarFallback }}
+            </AvatarFallback>
+          </Avatar>
+        </router-link>
+        <div v-else class="w-8 flex-shrink-0" />
+      </template>
 
       <!-- Bubble Wrapper with max 80% width -->
       <div
@@ -54,19 +61,45 @@
 
           <!-- Message Content -->
           <div
-            v-if="message.content_type === 'text'"
-            class="mb-1 native-html whitespace-pre-wrap"
-            :class="{ 'mb-3': message.attachments.length > 0 }"
+            ref="contentWrapperEl"
+            class="relative"
+            :class="{ 'max-h-[400px] overflow-hidden': isExpandable && !isExpanded }"
           >
-            {{ sanitizedContent }}
-          </div>
-          <div v-else ref="messageContentEl" @click="onMessageContentClick">
-            <Letter
-              :html="sanitizedContent"
-              :allowedSchemas="['cid', 'https', 'http', 'mailto']"
-              class="mb-1 native-html whitespace-pre-wrap break-words"
+            <div
+              v-if="message.content_type === 'text'"
+              class="mb-1 native-html whitespace-pre-wrap"
               :class="{ 'mb-3': message.attachments.length > 0 }"
-            />
+            >
+              {{ sanitizedContent }}
+            </div>
+            <div v-else ref="messageContentEl" @click="onMessageContentClick">
+              <Letter
+                :html="sanitizedContent"
+                :allowedSchemas="['cid', 'https', 'http', 'mailto']"
+                :allowed-css-properties="extendedCssProperties"
+                class="mb-1 native-html whitespace-pre-wrap break-words"
+                :class="{ 'mb-3': message.attachments.length > 0 }"
+              />
+            </div>
+
+            <div
+              v-if="isExpandable && !isExpanded"
+              class="absolute left-0 right-0 bottom-0 h-24 flex items-end justify-center pointer-events-none"
+              :class="
+                message.private
+                  ? 'bg-gradient-to-t from-private via-private/90 to-transparent'
+                  : 'bg-gradient-to-t from-background via-background/90 to-transparent'
+              "
+            >
+              <button
+                type="button"
+                @click="isExpanded = true"
+                class="pointer-events-auto flex items-center gap-1.5 text-xs font-medium text-foreground bg-accent hover:bg-accent/80 border border-border rounded-full px-3 py-1 mb-1 transition-colors duration-200"
+              >
+                <Maximize2 :size="12" />
+                {{ t('globals.terms.expand') }}
+              </button>
+            </div>
           </div>
 
           <ImageLightbox
@@ -116,28 +149,31 @@
       </div>
 
       <!-- Avatar (right for outgoing) -->
-      <router-link
-        v-if="isOutgoing && canManageUsers"
-        :to="{ name: 'edit-agent', params: { id: message.author?.id } }"
-        class="flex-shrink-0"
-      >
-        <Avatar class="cursor-pointer w-8 h-8 hover:opacity-80 transition-opacity">
+      <template v-if="isOutgoing">
+        <div v-if="groupWithPrev" class="w-8 flex-shrink-0" />
+        <router-link
+          v-else-if="canManageUsers"
+          :to="{ name: 'edit-agent', params: { id: message.author?.id } }"
+          class="flex-shrink-0"
+        >
+          <Avatar class="cursor-pointer w-8 h-8 hover:opacity-80 transition-opacity">
+            <AvatarImage :src="getAvatar" />
+            <AvatarFallback class="font-medium">
+              {{ avatarFallback }}
+            </AvatarFallback>
+          </Avatar>
+        </router-link>
+        <Avatar v-else class="w-8 h-8">
           <AvatarImage :src="getAvatar" />
           <AvatarFallback class="font-medium">
             {{ avatarFallback }}
           </AvatarFallback>
         </Avatar>
-      </router-link>
-      <Avatar v-else-if="isOutgoing" class="w-8 h-8">
-        <AvatarImage :src="getAvatar" />
-        <AvatarFallback class="font-medium">
-          {{ avatarFallback }}
-        </AvatarFallback>
-      </Avatar>
+      </template>
     </div>
 
     <!-- Timestamp tooltip -->
-    <div :class="isOutgoing ? 'pr-[47px]' : 'pl-[47px]'">
+    <div v-if="!groupWithNext" :class="isOutgoing ? 'pr-[47px]' : 'pl-[47px]'">
       <Tooltip>
         <TooltipTrigger>
           <span class="text-muted-foreground text-xs mt-1">
@@ -153,27 +189,61 @@
 </template>
 
 <script setup>
-import { computed, ref } from 'vue'
+import { computed, ref, onMounted, nextTick } from 'vue'
 import { useConversationStore } from '@main/stores/conversation'
 import { useUserStore } from '@main/stores/user'
 import { useI18n } from 'vue-i18n'
-import { Lock, Mail, RotateCcw, Check } from 'lucide-vue-next'
+import { Lock, Mail, RotateCcw, Check, Maximize2 } from 'lucide-vue-next'
 import { Tooltip, TooltipContent, TooltipTrigger } from '@shared-ui/components/ui/tooltip'
 import { Spinner } from '@shared-ui/components/ui/spinner'
 import { formatMessageTimestamp, formatFullTimestamp } from '@shared-ui/utils/datetime.js'
 import { Avatar, AvatarFallback, AvatarImage } from '@shared-ui/components/ui/avatar'
 import { Letter } from 'vue-letter'
+import { allowedCssProperties } from 'lettersanitizer'
 import ImageLightbox from '@/components/ImageLightbox.vue'
 import BubbleAttachmentPreview from '@main/features/conversation/message/attachment/BubbleAttachmentPreview.vue'
 import MessageEnvelope from './MessageEnvelope.vue'
 import CSATResponseDisplay from './CSATResponseDisplay.vue'
 import api from '@main/api'
 
+const extendedCssProperties = [...allowedCssProperties, 'transform', 'transform-origin']
+
+const COLLAPSE_THRESHOLD_PX = 400
+
+const contentWrapperEl = ref(null)
+const isExpandable = ref(false)
+const isExpanded = ref(false)
+
+const measureExpandable = () => {
+  const el = contentWrapperEl.value
+  if (!el) return
+  isExpandable.value = el.scrollHeight > COLLAPSE_THRESHOLD_PX
+}
+
+onMounted(async () => {
+  await nextTick()
+  measureExpandable()
+
+  // Email HTML images change height after initial paint - re-measure on load.
+  const imgs = contentWrapperEl.value?.querySelectorAll?.('img') ?? []
+  imgs.forEach((img) => {
+    if (!img.complete) img.addEventListener('load', measureExpandable, { once: true })
+  })
+})
+
 const props = defineProps({
   message: Object,
   direction: {
     type: String,
     validator: (v) => ['incoming', 'outgoing'].includes(v)
+  },
+  groupWithPrev: {
+    type: Boolean,
+    default: false
+  },
+  groupWithNext: {
+    type: Boolean,
+    default: false
   }
 })
 
diff --git a/frontend/apps/main/src/features/conversation/message/MessageList.vue b/frontend/apps/main/src/features/conversation/message/MessageList.vue
index a28dcba7..1e0cb289 100644
--- a/frontend/apps/main/src/features/conversation/message/MessageList.vue
+++ b/frontend/apps/main/src/features/conversation/message/MessageList.vue
@@ -22,24 +22,31 @@
 
         <MessagesSkeleton :count="10" v-if="conversationStore.messages.loading" />
 
-        <TransitionGroup v-else enter-active-class="animate-slide-in" tag="div" class="space-y-4">
+        <TransitionGroup v-else enter-active-class="animate-slide-in" tag="div">
           <div
-            v-for="(message, index) in conversationStore.conversationMessages"
-            :key="message.uuid"
-            :data-message-uuid="message.uuid"
-            :class="{
-              'my-2': message.type === 'activity',
-              'pt-4': index === 0
-            }"
+            v-for="row in messageRows"
+            :key="row.message.uuid"
+            :data-message-uuid="row.message.uuid"
+            :class="[row.spacingClass, { 'my-2': row.message.type === 'activity' }]"
           >
-            <div v-if="!message.private && message.type !== 'activity'">
-              <MessageBubble :message="message" :direction="message.type" />
+            <div v-if="!row.message.private && row.message.type !== 'activity'">
+              <MessageBubble
+                :message="row.message"
+                :direction="row.message.type"
+                :group-with-prev="row.groupWithPrev"
+                :group-with-next="row.groupWithNext"
+              />
             </div>
-            <div v-else-if="isPrivateNote(message)">
-              <MessageBubble :message="message" direction="outgoing" />
+            <div v-else-if="isPrivateNote(row.message)">
+              <MessageBubble
+                :message="row.message"
+                direction="outgoing"
+                :group-with-prev="row.groupWithPrev"
+                :group-with-next="row.groupWithNext"
+              />
             </div>
-            <div v-else-if="message.type === 'activity'">
-              <ActivityMessageBubble :message="message" />
+            <div v-else-if="row.message.type === 'activity'">
+              <ActivityMessageBubble :message="row.message" />
             </div>
           </div>
         </TransitionGroup>
@@ -61,7 +68,7 @@
 </template>
 
 <script setup>
-import { ref, onMounted, onUnmounted, watch } from 'vue'
+import { ref, computed, onMounted, onUnmounted, watch } from 'vue'
 import { useRoute } from 'vue-router'
 import MessageBubble from './MessageBubble.vue'
 import ActivityMessageBubble from './ActivityMessageBubble.vue'
@@ -219,6 +226,43 @@ watch(
 const isPrivateNote = (message) => {
   return message.type === 'outgoing' && message.private
 }
+
+const GROUP_WINDOW_MS = 60_000
+
+const canGroup = (a, b) => {
+  if (!a || !b) return false
+  if (a.type === 'activity' || b.type === 'activity') return false
+  if (a.type !== b.type) return false
+  if (Boolean(a.private) !== Boolean(b.private)) return false
+  if (a.status === 'failed' || b.status === 'failed') return false
+
+  const aSenderId = a.author?.id ?? a.sender_id
+  const bSenderId = b.author?.id ?? b.sender_id
+  if (!aSenderId || aSenderId !== bSenderId) return false
+
+  const aBucket = Math.floor(new Date(a.created_at).getTime() / GROUP_WINDOW_MS)
+  const bBucket = Math.floor(new Date(b.created_at).getTime() / GROUP_WINDOW_MS)
+  return aBucket === bBucket
+}
+
+const getSpacingClass = (index, groupWithPrev) => {
+  if (index === 0) return 'pt-4'
+  return groupWithPrev ? 'mt-1' : 'mt-4'
+}
+
+const messageRows = computed(() => {
+  const messages = conversationStore.conversationMessages
+  return messages.map((message, index) => {
+    const groupWithPrev = canGroup(messages[index - 1], message)
+    const groupWithNext = canGroup(message, messages[index + 1])
+    return {
+      message,
+      groupWithPrev,
+      groupWithNext,
+      spacingClass: getSpacingClass(index, groupWithPrev)
+    }
+  })
+})
 </script>
 
 <style scoped>
diff --git a/frontend/apps/widget/src/components/ChatMessages.vue b/frontend/apps/widget/src/components/ChatMessages.vue
index c4bfc005..4c80e1f7 100644
--- a/frontend/apps/widget/src/components/ChatMessages.vue
+++ b/frontend/apps/widget/src/components/ChatMessages.vue
@@ -65,6 +65,7 @@
             v-else
             :html="message.content"
             :allowedSchemas="['cid', 'https', 'http', 'mailto']"
+            :allowed-css-properties="extendedCssProperties"
             class="mb-1 native-html"
           />
           <div
@@ -151,6 +152,7 @@ import { useChatStore } from '../store/chat.js'
 import { useRelativeTime } from '@widget/composables/useRelativeTime.js'
 import { useI18n } from 'vue-i18n'
 import { Letter } from 'vue-letter'
+import { allowedCssProperties } from 'lettersanitizer'
 import ScrollToBottomButton from '@shared-ui/components/ScrollToBottomButton'
 import ChatIntro from './ChatIntro.vue'
 import NoticeBanner from './NoticeBanner.vue'
@@ -159,6 +161,8 @@ import CSATMessageBubble from './CSATMessageBubble.vue'
 import { TypingIndicator } from '@shared-ui/components/TypingIndicator'
 import { Spinner } from '@shared-ui/components/ui/spinner'
 
+const extendedCssProperties = [...allowedCssProperties, 'transform', 'transform-origin']
+
 const props = defineProps({
   showPreChatForm: {
     type: Boolean,
diff --git a/frontend/package.json b/frontend/package.json
index c5e48ee0..1fcc59c0 100644
--- a/frontend/package.json
+++ b/frontend/package.json
@@ -50,6 +50,7 @@
     "clsx": "^2.1.1",
     "codemirror": "^6.0.2",
     "date-fns": "^3.6.0",
+    "lettersanitizer": "^1.0.7",
     "lucide-vue-next": "^0.525.0",
     "mitt": "^3.0.1",
     "pinia": "^2.1.7",
@@ -61,7 +62,7 @@
     "vue": "^3.4.37",
     "vue-easy-lightbox": "^1.19.0",
     "vue-i18n": "9",
-    "vue-letter": "^0.2.0",
+    "vue-letter": "^0.2.1",
     "vue-picture-cropper": "^0.7.0",
     "vue-router": "^4.2.5",
     "vue-sonner": "^1.3.0",
diff --git a/frontend/pnpm-lock.yaml b/frontend/pnpm-lock.yaml
index 381cab37..9209d9da 100644
--- a/frontend/pnpm-lock.yaml
+++ b/frontend/pnpm-lock.yaml
@@ -98,6 +98,9 @@ importers:
       date-fns:
         specifier: ^3.6.0
         version: 3.6.0
+      lettersanitizer:
+        specifier: ^1.0.7
+        version: 1.0.7
       lucide-vue-next:
         specifier: ^0.525.0
         version: 0.525.0(vue@3.5.13(typescript@5.7.3))
@@ -132,8 +135,8 @@ importers:
         specifier: '9'
         version: 9.14.5(vue@3.5.13(typescript@5.7.3))
       vue-letter:
-        specifier: ^0.2.0
-        version: 0.2.0
+        specifier: ^0.2.1
+        version: 0.2.1
       vue-picture-cropper:
         specifier: ^0.7.0
         version: 0.7.0(vue@3.5.13(typescript@5.7.3))
@@ -2777,8 +2780,8 @@ packages:
   leaflet@1.7.1:
     resolution: {integrity: sha512-/xwPEBidtg69Q3HlqPdU3DnrXQOvQU/CCHA1tcDQVzOwm91YMYaILjNp7L4Eaw5Z4sOYdbBz6koWyibppd8Zqw==}
 
-  lettersanitizer@1.0.6:
-    resolution: {integrity: sha512-2vj0tUtBRjlmTCFsgVlFmfi04p049Zwv/4eBGWBUOKropEoL+q+jTQQfFyDu50j7gL76pycMvrqD0uV0vxX2zg==}
+  lettersanitizer@1.0.7:
+    resolution: {integrity: sha512-r+P8T0WxmoKmm5F96tPAyYFT4ef5YDXTVmWtZjHD9FA/T8dtYM+Rb2uIxb4IerwrDxG/toYN2SQXFo4RUy4mxQ==}
 
   levn@0.4.1:
     resolution: {integrity: sha512-+bT2uH4E5LGE7h/n3evcS/sQlJXCpIp6ym8OWJ5eV6+67Dsql/LaaT7qJBAt2rzfoa/5QBGBhxDix1dMt2kQKQ==}
@@ -3825,8 +3828,8 @@ packages:
     peerDependencies:
       vue: ^3.0.0
 
-  vue-letter@0.2.0:
-    resolution: {integrity: sha512-p4qHpw89GKidKyGcg4J4IjUcMQuVaTJq83c6UE4616claaLF9rj2Bg/Hq19uDCmokd+SvzEwxq6/ctfaaednkw==}
+  vue-letter@0.2.1:
+    resolution: {integrity: sha512-IYWp47XUikjKfEniWYlFxeJFKABZwAE5IEjz866qCBytBr2dzqVDdjoMDpBP//krxkzN/QZYyHe6C09y/IODYg==}
 
   vue-picture-cropper@0.7.0:
     resolution: {integrity: sha512-NF7+Dgso6d0GB16E5d/BbrcTIHm1VWz8dS3IjLhoBl+ZeC+yDA46CyJphQuO32SisaPmrKHN8VbiE2LgAfhnkQ==}
@@ -6650,7 +6653,7 @@ snapshots:
 
   leaflet@1.7.1: {}
 
-  lettersanitizer@1.0.6: {}
+  lettersanitizer@1.0.7: {}
 
   levn@0.4.1:
     dependencies:
@@ -7757,9 +7760,9 @@ snapshots:
       '@vue/devtools-api': 6.6.4
       vue: 3.5.13(typescript@5.7.3)
 
-  vue-letter@0.2.0:
+  vue-letter@0.2.1:
     dependencies:
-      lettersanitizer: 1.0.6
+      lettersanitizer: 1.0.7
 
   vue-picture-cropper@0.7.0(vue@3.5.13(typescript@5.7.3)):
     dependencies:
diff --git a/frontend/shared-ui/assets/styles/main.scss b/frontend/shared-ui/assets/styles/main.scss
index 16c17f5f..b0aa1364 100644
--- a/frontend/shared-ui/assets/styles/main.scss
+++ b/frontend/shared-ui/assets/styles/main.scss
@@ -103,7 +103,7 @@
     --sidebar-foreground: 240 5.9% 10%;
     --sidebar-primary: 240 5.9% 30%;
     --sidebar-primary-foreground: 0 0% 98%;
-    --sidebar-accent: 240 4.8% 95.9%;
+    --sidebar-accent: 240 5% 93%;
     --sidebar-accent-foreground: 240 5.9% 10%;
     --sidebar-border: 240 5% 88%;
     --sidebar-ring: 217.2 91.2% 59.8%;
@@ -113,7 +113,7 @@
     --sidebar-foreground: 0 0% 100%;
     --sidebar-primary: 235 86% 65%;
     --sidebar-primary-foreground: 0 0% 100%;
-    --sidebar-accent: 240 3.7% 15.9%;
+    --sidebar-accent: 240 5% 19%;
     --sidebar-accent-foreground: 240 4.8% 95.9%;
     --sidebar-border: 240 5% 14%;
     --sidebar-ring: 235 86% 65%;
@@ -150,7 +150,7 @@
     --muted: 240 4.8% 95.9%;
     --muted-foreground: 240 3.8% 46.1%;
 
-    --accent: 240 4.8% 95.9%;
+    --accent: 240 5% 93%;
     --accent-foreground: 240 5.9% 10%;
 
     --destructive: 0 84.2% 60.2%;
@@ -183,7 +183,7 @@
     --muted: 240 5% 16%;
     --muted-foreground: 240 4% 60%;
 
-    --accent: 240 3.7% 15.9%;
+    --accent: 240 5% 19%;
     --accent-foreground: 0 0% 98%;
 
     --destructive: 1 100% 69%;