diff --git a/app/controllers/api/v1/widget/messages_controller.rb b/app/controllers/api/v1/widget/messages_controller.rb
index a51b4c2d6..83b3dc8b1 100644
--- a/app/controllers/api/v1/widget/messages_controller.rb
+++ b/app/controllers/api/v1/widget/messages_controller.rb
@@ -43,7 +43,15 @@ class Api::V1::Widget::MessagesController < Api::V1::Widget::BaseController
   end
 
   def set_conversation
-    @conversation = create_conversation if conversation.nil?
+    return unless conversation.nil?
+
+    @conversation = create_conversation
+    apply_labels if permitted_params[:labels].present?
+  end
+
+  def apply_labels
+    valid_labels = inbox.account.labels.where(title: permitted_params[:labels]).pluck(:title)
+    @conversation.update_labels(valid_labels) if valid_labels.present?
   end
 
   def message_finder_params
@@ -64,7 +72,14 @@ class Api::V1::Widget::MessagesController < Api::V1::Widget::BaseController
 
   def permitted_params
     # timestamp parameter is used in create conversation method
-    params.permit(:id, :before, :after, :website_token, contact: [:name, :email], message: [:content, :referer_url, :timestamp, :echo_id, :reply_to])
+    # custom_attributes and labels are applied when a new conversation is created alongside the first message
+    params.permit(
+      :id, :before, :after, :website_token,
+      contact: [:name, :email],
+      message: [:content, :referer_url, :timestamp, :echo_id, :reply_to],
+      custom_attributes: {},
+      labels: []
+    )
   end
 
   def set_message
diff --git a/app/javascript/widget/api/conversation.js b/app/javascript/widget/api/conversation.js
index 1060b285d..05e81ff9f 100755
--- a/app/javascript/widget/api/conversation.js
+++ b/app/javascript/widget/api/conversation.js
@@ -6,13 +6,26 @@ const createConversationAPI = async content => {
   return API.post(urlData.url, urlData.params);
 };
 
-const sendMessageAPI = async (content, replyTo = null) => {
-  const urlData = endPoints.sendMessage(content, replyTo);
+const sendMessageAPI = async (
+  content,
+  replyTo = null,
+  { customAttributes, labels } = {}
+) => {
+  const urlData = endPoints.sendMessage(content, replyTo, {
+    customAttributes,
+    labels,
+  });
   return API.post(urlData.url, urlData.params);
 };
 
-const sendAttachmentAPI = async (attachment, replyTo = null) => {
-  const urlData = endPoints.sendAttachment(attachment, replyTo);
+const sendAttachmentAPI = async (
+  attachment,
+  { customAttributes, labels } = {}
+) => {
+  const urlData = endPoints.sendAttachment(attachment, {
+    customAttributes,
+    labels,
+  });
   return API.post(urlData.url, urlData.params);
 };
 
diff --git a/app/javascript/widget/api/endPoints.js b/app/javascript/widget/api/endPoints.js
index b595fdf00..713de56f1 100755
--- a/app/javascript/widget/api/endPoints.js
+++ b/app/javascript/widget/api/endPoints.js
@@ -22,23 +22,30 @@ const createConversation = params => {
   };
 };
 
-const sendMessage = (content, replyTo) => {
+const sendMessage = (content, replyTo, { customAttributes, labels } = {}) => {
   const referrerURL = window.referrerURL || '';
   const search = buildSearchParamsWithLocale(window.location.search);
-  return {
-    url: `/api/v1/widget/messages${search}`,
-    params: {
-      message: {
-        content,
-        reply_to: replyTo,
-        timestamp: new Date().toString(),
-        referer_url: referrerURL,
-      },
+  const params = {
+    message: {
+      content,
+      reply_to: replyTo,
+      timestamp: new Date().toString(),
+      referer_url: referrerURL,
     },
   };
+  if (customAttributes && Object.keys(customAttributes).length > 0) {
+    params.custom_attributes = customAttributes;
+  }
+  if (labels && labels.length > 0) {
+    params.labels = labels;
+  }
+  return { url: `/api/v1/widget/messages${search}`, params };
 };
 
-const sendAttachment = ({ attachment, replyTo = null }) => {
+const sendAttachment = (
+  { attachment, replyTo = null },
+  { customAttributes, labels } = {}
+) => {
   const { referrerURL = '' } = window;
   const timestamp = new Date().toString();
   const { file } = attachment;
@@ -55,6 +62,16 @@ const sendAttachment = ({ attachment, replyTo = null }) => {
   if (replyTo !== null) {
     formData.append('message[reply_to]', replyTo);
   }
+  if (customAttributes && Object.keys(customAttributes).length > 0) {
+    Object.entries(customAttributes).forEach(([key, value]) => {
+      formData.append(`custom_attributes[${key}]`, value);
+    });
+  }
+  if (labels && labels.length > 0) {
+    labels.forEach(label => {
+      formData.append('labels[]', label);
+    });
+  }
   return {
     url: `/api/v1/widget/messages${window.location.search}`,
     params: formData,
diff --git a/app/javascript/widget/api/specs/endPoints.spec.js b/app/javascript/widget/api/specs/endPoints.spec.js
index 0216caed9..b95b2f659 100644
--- a/app/javascript/widget/api/specs/endPoints.spec.js
+++ b/app/javascript/widget/api/specs/endPoints.spec.js
@@ -32,6 +32,50 @@ describe('#sendMessage', () => {
   });
 });
 
+describe('#sendMessage with pending metadata', () => {
+  it('includes custom_attributes and labels in payload', () => {
+    const spy = vi.spyOn(global, 'Date').mockImplementation(() => ({
+      toString: () => 'mock date',
+    }));
+    vi.spyOn(window, 'location', 'get').mockReturnValue({
+      ...window.location,
+      search: '?param=1',
+    });
+
+    window.WOOT_WIDGET = {
+      $root: { $i18n: { locale: 'ar' } },
+    };
+
+    const result = endPoints.sendMessage('hello', null, {
+      customAttributes: { plan: 'enterprise' },
+      labels: ['vip'],
+    });
+
+    expect(result.params.custom_attributes).toEqual({ plan: 'enterprise' });
+    expect(result.params.labels).toEqual(['vip']);
+    spy.mockRestore();
+  });
+
+  it('does not include metadata keys when not provided', () => {
+    const spy = vi.spyOn(global, 'Date').mockImplementation(() => ({
+      toString: () => 'mock date',
+    }));
+    vi.spyOn(window, 'location', 'get').mockReturnValue({
+      ...window.location,
+      search: '?param=1',
+    });
+
+    window.WOOT_WIDGET = {
+      $root: { $i18n: { locale: 'ar' } },
+    };
+
+    const result = endPoints.sendMessage('hello');
+    expect(result.params.custom_attributes).toBeUndefined();
+    expect(result.params.labels).toBeUndefined();
+    spy.mockRestore();
+  });
+});
+
 describe('#getConversation', () => {
   it('returns correct payload', () => {
     vi.spyOn(window, 'location', 'get').mockReturnValue({
diff --git a/app/javascript/widget/assets/scss/woot.scss b/app/javascript/widget/assets/scss/woot.scss
index 0044ccdfc..07aa6a0e3 100755
--- a/app/javascript/widget/assets/scss/woot.scss
+++ b/app/javascript/widget/assets/scss/woot.scss
@@ -7,7 +7,7 @@
 
 html,
 body {
-  @apply antialiased h-full bg-n-slate-2 dark:bg-n-solid-1;
+  @apply antialiased h-full;
 }
 
 .is-mobile {
diff --git a/app/javascript/widget/components/UserMessage.vue b/app/javascript/widget/components/UserMessage.vue
index a920c508d..25e119140 100755
--- a/app/javascript/widget/components/UserMessage.vue
+++ b/app/javascript/widget/components/UserMessage.vue
@@ -85,10 +85,9 @@ export default {
   },
   methods: {
     async retrySendMessage() {
-      await this.$store.dispatch(
-        'conversation/sendMessageWithData',
-        this.message
-      );
+      await this.$store.dispatch('conversation/sendMessageWithData', {
+        message: this.message,
+      });
     },
     onImageLoadError() {
       this.hasImageError = true;
diff --git a/app/javascript/widget/composables/useDarkMode.js b/app/javascript/widget/composables/useDarkMode.js
index 407d90980..bc19c456b 100644
--- a/app/javascript/widget/composables/useDarkMode.js
+++ b/app/javascript/widget/composables/useDarkMode.js
@@ -1,4 +1,4 @@
-import { computed, watchEffect } from 'vue';
+import { computed } from 'vue';
 import { useMapGetter } from 'dashboard/composables/store';
 
 const isDarkModeAuto = mode => mode === 'auto';
@@ -23,10 +23,6 @@ export function useDarkMode() {
     calculatePrefersDarkMode(darkMode.value, systemPreference.value)
   );
 
-  watchEffect(() => {
-    document.documentElement.classList.toggle('dark', prefersDarkMode.value);
-  });
-
   return {
     darkMode,
     prefersDarkMode,
diff --git a/app/javascript/widget/store/modules/conversation/actions.js b/app/javascript/widget/store/modules/conversation/actions.js
index 6d4c26610..aa08af615 100644
--- a/app/javascript/widget/store/modules/conversation/actions.js
+++ b/app/javascript/widget/store/modules/conversation/actions.js
@@ -30,18 +30,37 @@ export const actions = {
       commit('setConversationUIFlag', { isCreating: false });
     }
   },
-  sendMessage: async ({ dispatch }, params) => {
+  sendMessage: async ({ dispatch, state: conversationState }, params) => {
     const { content, replyTo } = params;
     const message = createTemporaryMessage({ content, replyTo });
-    dispatch('sendMessageWithData', message);
+    const { pendingCustomAttributes, pendingLabels } = conversationState;
+    dispatch('sendMessageWithData', {
+      message,
+      pendingCustomAttributes,
+      pendingLabels,
+    });
   },
-  sendMessageWithData: async ({ commit }, message) => {
+  sendMessageWithData: async (
+    { commit },
+    { message, pendingCustomAttributes = {}, pendingLabels = [] }
+  ) => {
     const { id, content, replyTo, meta = {} } = message;
+    const hasPendingMetadata =
+      Object.keys(pendingCustomAttributes).length > 0 ||
+      pendingLabels.length > 0;
 
     commit('pushMessageToConversation', message);
     commit('updateMessageMeta', { id, meta: { ...meta, error: '' } });
     try {
-      const { data } = await sendMessageAPI(content, replyTo);
+      const { data } = await sendMessageAPI(content, replyTo, {
+        customAttributes: hasPendingMetadata
+          ? pendingCustomAttributes
+          : undefined,
+        labels: hasPendingMetadata ? pendingLabels : undefined,
+      });
+      if (hasPendingMetadata) {
+        commit('clearPendingConversationMetadata');
+      }
 
       // [VITE] Don't delete this manually, since `pushMessageToConversation` does the replacement for us anyway
       // commit('deleteMessage', message.id);
@@ -59,7 +78,7 @@ export const actions = {
     commit('setLastMessageId');
   },
 
-  sendAttachment: async ({ commit }, params) => {
+  sendAttachment: async ({ commit, state: conversationState }, params) => {
     const {
       attachment: { thumbUrl, fileType },
       meta = {},
@@ -74,9 +93,22 @@ export const actions = {
       attachments: [attachment],
       replyTo: params.replyTo,
     });
+    const { pendingCustomAttributes, pendingLabels } = conversationState;
+    const hasPendingMetadata =
+      Object.keys(pendingCustomAttributes).length > 0 ||
+      pendingLabels.length > 0;
+
     commit('pushMessageToConversation', tempMessage);
     try {
-      const { data } = await sendAttachmentAPI(params);
+      const { data } = await sendAttachmentAPI(params, {
+        customAttributes: hasPendingMetadata
+          ? pendingCustomAttributes
+          : undefined,
+        labels: hasPendingMetadata ? pendingLabels : undefined,
+      });
+      if (hasPendingMetadata) {
+        commit('clearPendingConversationMetadata');
+      }
       commit('updateAttachmentMessageStatus', {
         message: data,
         tempId: tempMessage.id,
@@ -180,7 +212,14 @@ export const actions = {
     await toggleStatus();
   },
 
-  setCustomAttributes: async (_, customAttributes = {}) => {
+  setCustomAttributes: async (
+    { commit, rootGetters },
+    customAttributes = {}
+  ) => {
+    if (!rootGetters['conversationAttributes/getConversationParams']?.id) {
+      commit('setPendingCustomAttributes', customAttributes);
+      return;
+    }
     try {
       await setCustomAttributes(customAttributes);
     } catch (error) {
@@ -188,7 +227,11 @@ export const actions = {
     }
   },
 
-  deleteCustomAttribute: async (_, customAttribute) => {
+  deleteCustomAttribute: async ({ commit, rootGetters }, customAttribute) => {
+    if (!rootGetters['conversationAttributes/getConversationParams']?.id) {
+      commit('removePendingCustomAttribute', customAttribute);
+      return;
+    }
     try {
       await deleteCustomAttribute(customAttribute);
     } catch (error) {
diff --git a/app/javascript/widget/store/modules/conversation/getters.js b/app/javascript/widget/store/modules/conversation/getters.js
index 151694b86..ef1cd1cc3 100644
--- a/app/javascript/widget/store/modules/conversation/getters.js
+++ b/app/javascript/widget/store/modules/conversation/getters.js
@@ -33,6 +33,8 @@ export const getters = {
       messages: groupConversationBySender(conversationGroupedByDate[date]),
     }));
   },
+  getPendingCustomAttributes: _state => _state.pendingCustomAttributes,
+  getPendingLabels: _state => _state.pendingLabels,
   getIsFetchingList: _state => _state.uiFlags.isFetchingList,
   getMessageCount: _state => {
     return Object.values(_state.conversations).length;
diff --git a/app/javascript/widget/store/modules/conversation/index.js b/app/javascript/widget/store/modules/conversation/index.js
index 9869b6a87..077a16a04 100755
--- a/app/javascript/widget/store/modules/conversation/index.js
+++ b/app/javascript/widget/store/modules/conversation/index.js
@@ -14,6 +14,8 @@ const state = {
     isCreating: false,
   },
   lastMessageId: null,
+  pendingCustomAttributes: {},
+  pendingLabels: [],
 };
 
 export default {
diff --git a/app/javascript/widget/store/modules/conversation/mutations.js b/app/javascript/widget/store/modules/conversation/mutations.js
index 781dcd67b..1c23e008d 100644
--- a/app/javascript/widget/store/modules/conversation/mutations.js
+++ b/app/javascript/widget/store/modules/conversation/mutations.js
@@ -4,6 +4,8 @@ import { findUndeliveredMessage } from './helpers';
 export const mutations = {
   clearConversations($state) {
     $state.conversations = {};
+    $state.pendingCustomAttributes = {};
+    $state.pendingLabels = [];
   },
   pushMessageToConversation($state, message) {
     const { id, status, message_type: type } = message;
@@ -113,4 +115,31 @@ export const mutations = {
     const { id } = lastMessage;
     $state.lastMessageId = id;
   },
+
+  setPendingCustomAttributes($state, data) {
+    $state.pendingCustomAttributes = {
+      ...$state.pendingCustomAttributes,
+      ...data,
+    };
+  },
+
+  setPendingLabels($state, label) {
+    if (!$state.pendingLabels.includes(label)) {
+      $state.pendingLabels.push(label);
+    }
+  },
+
+  removePendingCustomAttribute($state, key) {
+    const { [key]: _, ...rest } = $state.pendingCustomAttributes;
+    $state.pendingCustomAttributes = rest;
+  },
+
+  removePendingLabel($state, label) {
+    $state.pendingLabels = $state.pendingLabels.filter(l => l !== label);
+  },
+
+  clearPendingConversationMetadata($state) {
+    $state.pendingCustomAttributes = {};
+    $state.pendingLabels = [];
+  },
 };
diff --git a/app/javascript/widget/store/modules/conversationLabels.js b/app/javascript/widget/store/modules/conversationLabels.js
index 3ae600082..ec3fc9fa4 100644
--- a/app/javascript/widget/store/modules/conversationLabels.js
+++ b/app/javascript/widget/store/modules/conversationLabels.js
@@ -5,14 +5,22 @@ const state = {};
 export const getters = {};
 
 export const actions = {
-  create: async (_, label) => {
+  create: async ({ commit, rootGetters }, label) => {
+    if (!rootGetters['conversationAttributes/getConversationParams']?.id) {
+      commit('conversation/setPendingLabels', label, { root: true });
+      return;
+    }
     try {
       await conversationLabels.create(label);
     } catch (error) {
       // Ignore error
     }
   },
-  destroy: async (_, label) => {
+  destroy: async ({ commit, rootGetters }, label) => {
+    if (!rootGetters['conversationAttributes/getConversationParams']?.id) {
+      commit('conversation/removePendingLabel', label, { root: true });
+      return;
+    }
     try {
       await conversationLabels.destroy(label);
     } catch (error) {
diff --git a/app/javascript/widget/store/modules/specs/conversation/actions.spec.js b/app/javascript/widget/store/modules/specs/conversation/actions.spec.js
index 39b8afe1a..2ab17cb37 100644
--- a/app/javascript/widget/store/modules/specs/conversation/actions.spec.js
+++ b/app/javascript/widget/store/modules/specs/conversation/actions.spec.js
@@ -111,20 +111,45 @@ describe('#actions', () => {
           search: '?param=1',
         },
       }));
+      const state = { pendingCustomAttributes: {}, pendingLabels: [] };
       await actions.sendMessage(
-        { commit, dispatch },
+        { commit, dispatch, state },
         { content: 'hello', replyTo: 124 }
       );
       spy.mockRestore();
       windowSpy.mockRestore();
       expect(dispatch).toBeCalledWith('sendMessageWithData', {
-        attachments: undefined,
-        content: 'hello',
-        created_at: 1466424490,
-        id: '1111',
-        message_type: 0,
-        replyTo: 124,
-        status: 'in_progress',
+        message: {
+          attachments: undefined,
+          content: 'hello',
+          created_at: 1466424490,
+          id: '1111',
+          message_type: 0,
+          replyTo: 124,
+          status: 'in_progress',
+        },
+        pendingCustomAttributes: {},
+        pendingLabels: [],
+      });
+    });
+
+    it('includes pending metadata when available', async () => {
+      const mockDate = new Date(1466424490000);
+      getUuid.mockImplementationOnce(() => '2222');
+      const spy = vi.spyOn(global, 'Date').mockImplementation(() => mockDate);
+      const state = {
+        pendingCustomAttributes: { plan: 'enterprise' },
+        pendingLabels: ['vip'],
+      };
+      await actions.sendMessage(
+        { commit, dispatch, state },
+        { content: 'hello' }
+      );
+      spy.mockRestore();
+      expect(dispatch).toBeCalledWith('sendMessageWithData', {
+        message: expect.objectContaining({ content: 'hello' }),
+        pendingCustomAttributes: { plan: 'enterprise' },
+        pendingLabels: ['vip'],
       });
     });
   });
@@ -136,9 +161,10 @@ describe('#actions', () => {
       const spy = vi.spyOn(global, 'Date').mockImplementation(() => mockDate);
       const thumbUrl = '';
       const attachment = { thumbUrl, fileType: 'file' };
+      const state = { pendingCustomAttributes: {}, pendingLabels: [] };
 
       actions.sendAttachment(
-        { commit, dispatch },
+        { commit, dispatch, state },
         { attachment, replyTo: 135 }
       );
       spy.mockRestore();
@@ -180,6 +206,58 @@ describe('#actions', () => {
     });
   });
 
+  describe('#setCustomAttributes', () => {
+    it('queues to pending state when no conversation exists', async () => {
+      const rootGetters = {
+        'conversationAttributes/getConversationParams': { id: '' },
+      };
+      await actions.setCustomAttributes(
+        { commit, rootGetters },
+        { plan: 'enterprise' }
+      );
+      expect(commit).toBeCalledWith('setPendingCustomAttributes', {
+        plan: 'enterprise',
+      });
+    });
+
+    it('calls API when conversation exists', async () => {
+      API.post.mockResolvedValue({ data: {} });
+      const rootGetters = {
+        'conversationAttributes/getConversationParams': { id: 123 },
+      };
+      await actions.setCustomAttributes(
+        { commit, rootGetters },
+        { plan: 'enterprise' }
+      );
+      expect(commit).not.toBeCalledWith(
+        'setPendingCustomAttributes',
+        expect.anything()
+      );
+    });
+  });
+
+  describe('#deleteCustomAttribute', () => {
+    it('removes from pending state when no conversation exists', async () => {
+      const rootGetters = {
+        'conversationAttributes/getConversationParams': { id: '' },
+      };
+      await actions.deleteCustomAttribute({ commit, rootGetters }, 'plan');
+      expect(commit).toBeCalledWith('removePendingCustomAttribute', 'plan');
+    });
+
+    it('calls API when conversation exists', async () => {
+      API.post.mockResolvedValue({ data: {} });
+      const rootGetters = {
+        'conversationAttributes/getConversationParams': { id: 123 },
+      };
+      await actions.deleteCustomAttribute({ commit, rootGetters }, 'plan');
+      expect(commit).not.toBeCalledWith(
+        'removePendingCustomAttribute',
+        expect.anything()
+      );
+    });
+  });
+
   describe('#clearConversations', () => {
     it('sends correct mutations', () => {
       actions.clearConversations({ commit });
diff --git a/app/javascript/widget/store/modules/specs/conversation/mutations.spec.js b/app/javascript/widget/store/modules/specs/conversation/mutations.spec.js
index bc6b6bd29..0894c5b52 100644
--- a/app/javascript/widget/store/modules/specs/conversation/mutations.spec.js
+++ b/app/javascript/widget/store/modules/specs/conversation/mutations.spec.js
@@ -169,10 +169,77 @@ describe('#mutations', () => {
   });
 
   describe('#clearConversations', () => {
-    it('clears the state', () => {
-      const state = { conversations: { 1: { id: 1 } } };
+    it('clears conversations and pending metadata', () => {
+      const state = {
+        conversations: { 1: { id: 1 } },
+        pendingCustomAttributes: { plan: 'enterprise' },
+        pendingLabels: ['vip'],
+      };
       mutations.clearConversations(state);
       expect(state.conversations).toEqual({});
+      expect(state.pendingCustomAttributes).toEqual({});
+      expect(state.pendingLabels).toEqual([]);
+    });
+  });
+
+  describe('#setPendingCustomAttributes', () => {
+    it('merges custom attributes into pending state', () => {
+      const state = { pendingCustomAttributes: { existing: 'value' } };
+      mutations.setPendingCustomAttributes(state, { plan: 'enterprise' });
+      expect(state.pendingCustomAttributes).toEqual({
+        existing: 'value',
+        plan: 'enterprise',
+      });
+    });
+  });
+
+  describe('#setPendingLabels', () => {
+    it('adds label to pending state', () => {
+      const state = { pendingLabels: [] };
+      mutations.setPendingLabels(state, 'vip');
+      expect(state.pendingLabels).toEqual(['vip']);
+    });
+
+    it('does not add duplicate labels', () => {
+      const state = { pendingLabels: ['vip'] };
+      mutations.setPendingLabels(state, 'vip');
+      expect(state.pendingLabels).toEqual(['vip']);
+    });
+  });
+
+  describe('#removePendingCustomAttribute', () => {
+    it('removes a single key from pending custom attributes', () => {
+      const state = {
+        pendingCustomAttributes: { plan: 'enterprise', region: 'us' },
+      };
+      mutations.removePendingCustomAttribute(state, 'plan');
+      expect(state.pendingCustomAttributes).toEqual({ region: 'us' });
+    });
+  });
+
+  describe('#removePendingLabel', () => {
+    it('removes a label from pending labels', () => {
+      const state = { pendingLabels: ['vip', 'premium'] };
+      mutations.removePendingLabel(state, 'vip');
+      expect(state.pendingLabels).toEqual(['premium']);
+    });
+
+    it('does nothing if label not present', () => {
+      const state = { pendingLabels: ['vip'] };
+      mutations.removePendingLabel(state, 'premium');
+      expect(state.pendingLabels).toEqual(['vip']);
+    });
+  });
+
+  describe('#clearPendingConversationMetadata', () => {
+    it('clears pending custom attributes and labels', () => {
+      const state = {
+        pendingCustomAttributes: { plan: 'enterprise' },
+        pendingLabels: ['vip'],
+      };
+      mutations.clearPendingConversationMetadata(state);
+      expect(state.pendingCustomAttributes).toEqual({});
+      expect(state.pendingLabels).toEqual([]);
     });
   });
 
diff --git a/app/javascript/widget/views/ArticleViewer.vue b/app/javascript/widget/views/ArticleViewer.vue
index bc4cf775c..9289d0546 100644
--- a/app/javascript/widget/views/ArticleViewer.vue
+++ b/app/javascript/widget/views/ArticleViewer.vue
@@ -10,7 +10,7 @@ export default {
 </script>
 
 <template>
-  <div class="bg-n-solid-1 h-full">
+  <div class="bg-white h-full">
     <IframeLoader :url="$route.query.link" />
   </div>
 </template>
diff --git a/app/listeners/agent_bot_listener.rb b/app/listeners/agent_bot_listener.rb
index ccac8005f..8fdf964fb 100644
--- a/app/listeners/agent_bot_listener.rb
+++ b/app/listeners/agent_bot_listener.rb
@@ -15,6 +15,14 @@ class AgentBotListener < BaseListener
     agent_bots_for(inbox, conversation).each { |agent_bot| process_webhook_bot_event(agent_bot, payload) }
   end
 
+  def conversation_updated(event)
+    conversation = extract_conversation_and_account(event)[0]
+    inbox = conversation.inbox
+    event_name = __method__.to_s
+    payload = conversation.webhook_data.merge(event: event_name)
+    agent_bots_for(inbox, conversation).each { |agent_bot| process_webhook_bot_event(agent_bot, payload) }
+  end
+
   def message_created(event)
     message = extract_message_and_account(event)[0]
     inbox = message.inbox
diff --git a/app/models/attachment.rb b/app/models/attachment.rb
index a1cc062a0..769e134be 100644
--- a/app/models/attachment.rb
+++ b/app/models/attachment.rb
@@ -37,6 +37,7 @@ class Attachment < ApplicationRecord
   belongs_to :account
   belongs_to :message
   has_one_attached :file
+  before_save :set_extension
   validate :acceptable_file
   validates :external_url, length: { maximum: Limits::URL_LENGTH_LIMIT }
   enum file_type: { :image => 0, :audio => 1, :video => 2, :file => 3, :location => 4, :fallback => 5, :share => 6, :story_mention => 7,
@@ -111,6 +112,7 @@ class Attachment < ApplicationRecord
   def file_metadata
     metadata = {
       extension: extension,
+      content_type: file.content_type,
       data_url: file_url,
       thumb_url: thumb_url,
       file_size: file.byte_size,
@@ -118,7 +120,7 @@ class Attachment < ApplicationRecord
       height: file.metadata[:height]
     }
 
-    metadata[:data_url] = metadata[:thumb_url] = external_url if message.inbox.instagram? && message.incoming?
+    metadata[:data_url] = metadata[:thumb_url] = external_url if instagram_incoming_message?
     metadata
   end
 
@@ -154,6 +156,21 @@ class Attachment < ApplicationRecord
     }
   end
 
+  def instagram_incoming_message?
+    return false unless message.incoming?
+
+    return true if message.inbox.instagram_direct?
+
+    message.inbox.instagram? && message.conversation&.additional_attributes&.dig('type') == 'instagram_direct_message'
+  end
+
+  def set_extension
+    return unless file.attached?
+    return if extension.present?
+
+    self.extension = File.extname(file.filename.to_s).delete_prefix('.').presence
+  end
+
   def should_validate_file?
     return unless file.attached?
     # we are only limiting attachment types in case of website widget
diff --git a/app/views/layouts/portal.html.erb b/app/views/layouts/portal.html.erb
index 52d8e2789..78418881a 100644
--- a/app/views/layouts/portal.html.erb
+++ b/app/views/layouts/portal.html.erb
@@ -58,9 +58,9 @@ By default, it renders:
       }
     </script>
   </head>
-  <body class="bg-white dark:bg-slate-900">
+  <body>
     <div id="portal" class="antialiased">
-      <main class="flex flex-col min-h-screen main-content" role="main">
+      <main class="flex flex-col min-h-screen bg-white main-content dark:bg-slate-900" role="main">
         <% if !@is_plain_layout_enabled %>
           <%= render "public/api/v1/portals/header", portal: @portal %>
         <% end %>
diff --git a/enterprise/app/controllers/enterprise/super_admin/accounts_controller.rb b/enterprise/app/controllers/enterprise/super_admin/accounts_controller.rb
index 305699dcb..23a8cc5de 100644
--- a/enterprise/app/controllers/enterprise/super_admin/accounts_controller.rb
+++ b/enterprise/app/controllers/enterprise/super_admin/accounts_controller.rb
@@ -1,4 +1,15 @@
 module Enterprise::SuperAdmin::AccountsController
+  def create
+    manually_managed = params[:account]&.delete(:manually_managed_features)
+
+    super do |resource|
+      if manually_managed.present?
+        service = ::Internal::Accounts::InternalAttributesService.new(resource)
+        service.manually_managed_features = manually_managed
+      end
+    end
+  end
+
   def update
     # Handle manually managed features from form submission
     if params[:account] && params[:account][:manually_managed_features].present?
diff --git a/spec/controllers/api/v1/widget/messages_controller_spec.rb b/spec/controllers/api/v1/widget/messages_controller_spec.rb
index 11c916514..902b4ec01 100644
--- a/spec/controllers/api/v1/widget/messages_controller_spec.rb
+++ b/spec/controllers/api/v1/widget/messages_controller_spec.rb
@@ -56,6 +56,65 @@ RSpec.describe '/api/v1/widget/messages', type: :request do
         expect(json_response['content']).to eq(message_params[:content])
       end
 
+      it 'creates conversation with custom_attributes when first message is sent' do
+        conversation.destroy!
+        message_params = { content: 'hello world', timestamp: Time.current }
+        custom_attributes = { plan: 'enterprise', source: 'website' }
+        post api_v1_widget_messages_url,
+             params: { website_token: web_widget.website_token, message: message_params, custom_attributes: custom_attributes },
+             headers: { 'X-Auth-Token' => token },
+             as: :json
+
+        expect(response).to have_http_status(:success)
+        new_conversation = contact.conversations.last
+        expect(new_conversation.custom_attributes).to include('plan' => 'enterprise', 'source' => 'website')
+      end
+
+      it 'creates conversation with labels when first message is sent' do
+        conversation.destroy!
+        label = create(:label, title: 'vip', account: account)
+        message_params = { content: 'hello world', timestamp: Time.current }
+        post api_v1_widget_messages_url,
+             params: { website_token: web_widget.website_token, message: message_params, labels: [label.title] },
+             headers: { 'X-Auth-Token' => token },
+             as: :json
+
+        expect(response).to have_http_status(:success)
+        new_conversation = contact.conversations.last
+        expect(new_conversation.label_list).to include('vip')
+      end
+
+      it 'ignores invalid labels when creating conversation with first message' do
+        conversation.destroy!
+        create(:label, title: 'valid-label', account: account)
+        message_params = { content: 'hello world', timestamp: Time.current }
+        post api_v1_widget_messages_url,
+             params: { website_token: web_widget.website_token, message: message_params, labels: %w[valid-label nonexistent] },
+             headers: { 'X-Auth-Token' => token },
+             as: :json
+
+        expect(response).to have_http_status(:success)
+        new_conversation = contact.conversations.last
+        expect(new_conversation.label_list).to include('valid-label')
+        expect(new_conversation.label_list).not_to include('nonexistent')
+      end
+
+      it 'does not apply labels or custom_attributes when conversation already exists' do
+        create(:label, title: 'vip', account: account)
+        message_params = { content: 'hello world', timestamp: Time.current }
+        custom_attributes = { plan: 'enterprise' }
+        post api_v1_widget_messages_url,
+             params: { website_token: web_widget.website_token, message: message_params,
+                       custom_attributes: custom_attributes, labels: ['vip'] },
+             headers: { 'X-Auth-Token' => token },
+             as: :json
+
+        expect(response).to have_http_status(:success)
+        conversation.reload
+        expect(conversation.custom_attributes).not_to include('plan' => 'enterprise')
+        expect(conversation.label_list).not_to include('vip')
+      end
+
       it 'does not create the message' do
         conversation.destroy! # Test all params
         message_params = { content: "#{'h' * 150 * 1000}a", timestamp: Time.current }
diff --git a/spec/listeners/agent_bot_listener_spec.rb b/spec/listeners/agent_bot_listener_spec.rb
index 56c478a1b..24af37383 100644
--- a/spec/listeners/agent_bot_listener_spec.rb
+++ b/spec/listeners/agent_bot_listener_spec.rb
@@ -57,6 +57,39 @@ describe AgentBotListener do
     end
   end
 
+  describe '#conversation_updated' do
+    let(:event_name) { 'conversation.updated' }
+    let!(:event) { Events::Base.new(event_name, Time.zone.now, conversation: conversation) }
+
+    context 'when agent bot is not configured' do
+      it 'does not send webhook' do
+        expect(AgentBots::WebhookJob).not_to receive(:perform_later)
+        listener.conversation_updated(event)
+      end
+    end
+
+    context 'when agent bot is configured on inbox' do
+      it 'sends webhook to the inbox agent bot' do
+        create(:agent_bot_inbox, inbox: inbox, agent_bot: agent_bot)
+        expect(AgentBots::WebhookJob).to receive(:perform_later).with(agent_bot.outgoing_url,
+                                                                      conversation.webhook_data.merge(event: 'conversation_updated')).once
+        listener.conversation_updated(event)
+      end
+    end
+
+    context 'when conversation is assigned to an agent bot' do
+      before do
+        conversation.update!(assignee_agent_bot: agent_bot, assignee: nil)
+      end
+
+      it 'sends webhook to the assigned agent bot' do
+        expect(AgentBots::WebhookJob).to receive(:perform_later).with(agent_bot.outgoing_url,
+                                                                      conversation.webhook_data.merge(event: 'conversation_updated')).once
+        listener.conversation_updated(event)
+      end
+    end
+  end
+
   describe '#webwidget_triggered' do
     let(:event_name) { 'webwidget.triggered' }
 
diff --git a/spec/models/attachment_spec.rb b/spec/models/attachment_spec.rb
index a17839174..82fb51bf1 100644
--- a/spec/models/attachment_spec.rb
+++ b/spec/models/attachment_spec.rb
@@ -57,11 +57,6 @@ RSpec.describe Attachment do
       }.to_json, headers: {})
     end
 
-    it 'returns external url as data and thumb urls when message is incoming' do
-      external_url = instagram_message.attachments.first.external_url
-      expect(instagram_message.attachments.first.push_event_data[:data_url]).to eq external_url
-    end
-
     it 'returns original attachment url as data url if the message is outgoing' do
       message = create(:message, :instagram_story_mention, message_type: :outgoing)
       expect(message.attachments.first.push_event_data[:data_url]).not_to eq message.attachments.first.external_url
@@ -155,6 +150,83 @@ RSpec.describe Attachment do
     end
   end
 
+  describe 'push_event_data for instagram direct message attachments' do
+    let(:account) { create(:account) }
+    let(:instagram_inbox) do
+      create(:inbox, account: account,
+                     channel: create(:channel_instagram_fb_page, account: account, instagram_id: 'instagram-dm-test'))
+    end
+
+    context 'when conversation type is instagram_direct_message' do
+      let(:conversation) do
+        create(:conversation, account: account, inbox: instagram_inbox,
+                              additional_attributes: { 'type' => 'instagram_direct_message' })
+      end
+      let(:instagram_message) { create(:message, account: account, inbox: instagram_inbox, conversation: conversation, message_type: :incoming) }
+
+      it 'uses external_url for data_url and thumb_url' do
+        attachment = instagram_message.attachments.new(account_id: account.id, file_type: :image, external_url: 'https://instagram.com/image.jpg')
+        attachment.file.attach(io: Rails.root.join('spec/assets/avatar.png').open, filename: 'avatar.png', content_type: 'image/png')
+        attachment.save!
+
+        event_data = attachment.push_event_data
+        expect(event_data[:data_url]).to eq('https://instagram.com/image.jpg')
+        expect(event_data[:thumb_url]).to eq('https://instagram.com/image.jpg')
+      end
+    end
+
+    context 'when conversation type is not instagram_direct_message' do
+      let(:conversation) do
+        create(:conversation, account: account, inbox: instagram_inbox,
+                              additional_attributes: { 'type' => 'other_type' })
+      end
+      let(:instagram_message) { create(:message, account: account, inbox: instagram_inbox, conversation: conversation, message_type: :incoming) }
+
+      it 'uses file_url for data_url instead of external_url' do
+        attachment = instagram_message.attachments.new(account_id: account.id, file_type: :image, external_url: 'https://instagram.com/image.jpg')
+        attachment.file.attach(io: Rails.root.join('spec/assets/avatar.png').open, filename: 'avatar.png', content_type: 'image/png')
+        attachment.save!
+
+        event_data = attachment.push_event_data
+        expect(event_data[:data_url]).not_to eq('https://instagram.com/image.jpg')
+      end
+    end
+
+    context 'when message is outgoing on instagram DM conversation' do
+      let(:conversation) do
+        create(:conversation, account: account, inbox: instagram_inbox,
+                              additional_attributes: { 'type' => 'instagram_direct_message' })
+      end
+      let(:outgoing_message) { create(:message, account: account, inbox: instagram_inbox, conversation: conversation, message_type: :outgoing) }
+
+      it 'does not override data_url with external_url' do
+        attachment = outgoing_message.attachments.new(account_id: account.id, file_type: :image, external_url: 'https://instagram.com/image.jpg')
+        attachment.file.attach(io: Rails.root.join('spec/assets/avatar.png').open, filename: 'avatar.png', content_type: 'image/png')
+        attachment.save!
+
+        event_data = attachment.push_event_data
+        expect(event_data[:data_url]).not_to eq('https://instagram.com/image.jpg')
+      end
+    end
+
+    context 'when inbox is Channel::Instagram (direct login)' do
+      let(:instagram_channel) { create(:channel_instagram, account: account) }
+      let(:direct_inbox) { instagram_channel.inbox }
+      let(:conversation) { create(:conversation, account: account, inbox: direct_inbox) }
+      let(:incoming_message) { create(:message, account: account, inbox: direct_inbox, conversation: conversation, message_type: :incoming) }
+
+      it 'uses external_url for data_url and thumb_url' do
+        attachment = incoming_message.attachments.new(account_id: account.id, file_type: :image, external_url: 'https://instagram.com/image.jpg')
+        attachment.file.attach(io: Rails.root.join('spec/assets/avatar.png').open, filename: 'avatar.png', content_type: 'image/png')
+        attachment.save!
+
+        event_data = attachment.push_event_data
+        expect(event_data[:data_url]).to eq('https://instagram.com/image.jpg')
+        expect(event_data[:thumb_url]).to eq('https://instagram.com/image.jpg')
+      end
+    end
+  end
+
   describe 'push_event_data for ig_reel attachments' do
     it 'returns external_url as data_url when no file is attached' do
       attachment = message.attachments.create!(
@@ -187,6 +259,44 @@ RSpec.describe Attachment do
     end
   end
 
+  describe 'set_extension' do
+    it 'sets extension from filename on save' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file)
+      attachment.file.attach(io: StringIO.new('fake pdf'), filename: 'test.pdf', content_type: 'application/pdf')
+      attachment.save!
+
+      expect(attachment.extension).to eq('pdf')
+    end
+
+    it 'does not overwrite extension if already set' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file, extension: 'doc')
+      attachment.file.attach(io: StringIO.new('fake pdf'), filename: 'test.pdf', content_type: 'application/pdf')
+      attachment.save!
+
+      expect(attachment.extension).to eq('doc')
+    end
+
+    it 'handles filenames without extension' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file)
+      attachment.file.attach(io: StringIO.new('fake data'), filename: 'README', content_type: 'text/plain')
+      attachment.save!
+
+      expect(attachment.extension).to be_nil
+    end
+  end
+
+  describe 'push_event_data includes extension and content_type' do
+    it 'returns extension and content_type for file attachments' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file)
+      attachment.file.attach(io: StringIO.new('fake pdf'), filename: 'test.pdf', content_type: 'application/pdf')
+      attachment.save!
+
+      event_data = attachment.push_event_data
+      expect(event_data[:extension]).to eq('pdf')
+      expect(event_data[:content_type]).to eq('application/pdf')
+    end
+  end
+
   describe 'file size validation' do
     let(:attachment) { message.attachments.new(account_id: message.account_id, file_type: :image) }