diff --git a/app/builders/messages/message_builder.rb b/app/builders/messages/message_builder.rb
index a01df50c4..0eeba6b95 100644
--- a/app/builders/messages/message_builder.rb
+++ b/app/builders/messages/message_builder.rb
@@ -41,7 +41,7 @@ class Messages::MessageBuilder
   def build_message
     @message = conversation.messages.create!(message_params)
     (response.attachments || []).each do |attachment|
-      attachment_obj = @message.build_attachment(attachment_params(attachment).except(:remote_file_url))
+      attachment_obj = @message.attachments.new(attachment_params(attachment).except(:remote_file_url))
       attachment_obj.save!
       attach_file(attachment_obj, attachment_params(attachment)[:remote_file_url]) if attachment_params(attachment)[:remote_file_url]
     end
diff --git a/app/builders/messages/outgoing/normal_builder.rb b/app/builders/messages/outgoing/normal_builder.rb
index c420b2a41..3b44fcd0e 100644
--- a/app/builders/messages/outgoing/normal_builder.rb
+++ b/app/builders/messages/outgoing/normal_builder.rb
@@ -10,19 +10,22 @@ class Messages::Outgoing::NormalBuilder
     @fb_id = params[:fb_id]
     @content_type = params[:content_type]
     @items = params.to_unsafe_h&.dig(:content_attributes, :items)
-    @attachment = params[:attachment]
+    @attachments = params[:attachments]
   end
 
   def perform
     @message = @conversation.messages.build(message_params)
-    if @attachment
-      @message.attachment = Attachment.new(
-        account_id: message.account_id,
-        file_type: file_type(@attachment[:file]&.content_type)
-      )
-      @message.attachment.file.attach(@attachment[:file])
-    end
     @message.save
+    if @attachments.present?
+      @attachments.each do |uploaded_attachment|
+        attachment = @message.attachments.new(
+          account_id: @message.account_id,
+          file_type: file_type(uploaded_attachment&.content_type)
+        )
+        attachment.file.attach(uploaded_attachment)
+      end
+      @message.save
+    end
     @message
   end
 
diff --git a/app/controllers/api/v1/widget/messages_controller.rb b/app/controllers/api/v1/widget/messages_controller.rb
index 7e0c446ea..a65e01f9c 100644
--- a/app/controllers/api/v1/widget/messages_controller.rb
+++ b/app/controllers/api/v1/widget/messages_controller.rb
@@ -10,8 +10,8 @@ class Api::V1::Widget::MessagesController < Api::V1::Widget::BaseController
 
   def create
     @message = conversation.messages.new(message_params)
+    @message.save
     build_attachment
-    @message.save!
   end
 
   def update
@@ -28,13 +28,16 @@ class Api::V1::Widget::MessagesController < Api::V1::Widget::BaseController
   private
 
   def build_attachment
-    return if params[:message][:attachment].blank?
+    return if params[:message][:attachments].blank?
 
-    @message.attachment = Attachment.new(
-      account_id: @message.account_id,
-      file_type: helpers.file_type(params[:message][:attachment][:file]&.content_type)
-    )
-    @message.attachment.file.attach(params[:message][:attachment][:file])
+    params[:message][:attachments].each do |uploaded_attachment|
+      attachment = @message.attachments.new(
+        account_id: @message.account_id,
+        file_type: helpers.file_type(uploaded_attachment&.content_type)
+      )
+      attachment.file.attach(uploaded_attachment)
+    end
+    @message.save!
   end
 
   def set_conversation
diff --git a/app/finders/message_finder.rb b/app/finders/message_finder.rb
index f21093b48..00ef8ab3b 100644
--- a/app/finders/message_finder.rb
+++ b/app/finders/message_finder.rb
@@ -11,7 +11,7 @@ class MessageFinder
   private
 
   def conversation_messages
-    @conversation.messages.includes(:attachment, user: { avatar_attachment: :blob })
+    @conversation.messages.includes(:attachments, user: { avatar_attachment: :blob })
   end
 
   def messages
diff --git a/app/javascript/dashboard/api/inbox/message.js b/app/javascript/dashboard/api/inbox/message.js
index 4ceac84d0..c9681f685 100644
--- a/app/javascript/dashboard/api/inbox/message.js
+++ b/app/javascript/dashboard/api/inbox/message.js
@@ -22,7 +22,7 @@ class MessageApi extends ApiClient {
 
   sendAttachment([conversationId, { file }]) {
     const formData = new FormData();
-    formData.append('attachment[file]', file);
+    formData.append('attachments[]', file, file.name);
     return axios({
       method: 'post',
       url: `${this.url}/${conversationId}/messages`,
diff --git a/app/javascript/dashboard/components/widgets/conversation/ConversationCard.vue b/app/javascript/dashboard/components/widgets/conversation/ConversationCard.vue
index 7292344f8..4afe61c31 100644
--- a/app/javascript/dashboard/components/widgets/conversation/ConversationCard.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/ConversationCard.vue
@@ -105,15 +105,17 @@ export default {
       router.push({ path: frontendURL(path) });
     },
     extractMessageText(chatItem) {
-      if (chatItem.content) {
-        return chatItem.content;
+      const { content, attachments } = chatItem;
+
+      if (content) {
+        return content;
       }
-      let fileType = '';
-      if (chatItem.attachment) {
-        fileType = chatItem.attachment.file_type;
-      } else {
+      if (!attachments) {
         return ' ';
       }
+
+      const [attachment] = attachments;
+      const { file_type: fileType } = attachment;
       const key = `CHAT_LIST.ATTACHMENTS.${fileType}`;
       return `
         <i class="small-icon ${this.$t(`${key}.ICON`)}"></i>
diff --git a/app/javascript/dashboard/components/widgets/conversation/Message.vue b/app/javascript/dashboard/components/widgets/conversation/Message.vue
index 7095b2d86..4ef1ddb4c 100644
--- a/app/javascript/dashboard/components/widgets/conversation/Message.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/Message.vue
@@ -1,22 +1,26 @@
 <template>
-  <li v-if="data.attachment || data.content" :class="alignBubble">
+  <li v-if="hasAttachments || data.content" :class="alignBubble">
     <div :class="wrapClass">
       <p v-tooltip.top-start="sentByMessage" :class="bubbleClass">
-        <bubble-image
-          v-if="data.attachment && data.attachment.file_type === 'image'"
-          :url="data.attachment.data_url"
-          :readable-time="readableTime"
-        />
-        <bubble-file
-          v-if="data.attachment && data.attachment.file_type !== 'image'"
-          :url="data.attachment.data_url"
-          :readable-time="readableTime"
-        />
         <bubble-text
           v-if="data.content"
           :message="message"
           :readable-time="readableTime"
         />
+        <span v-if="hasAttachments">
+          <span v-for="attachment in data.attachments" :key="attachment.id">
+            <bubble-image
+              v-if="attachment.file_type === 'image'"
+              :url="attachment.data_url"
+              :readable-time="readableTime"
+            />
+            <bubble-file
+              v-if="attachment.file_type !== 'image'"
+              :url="attachment.data_url"
+              :readable-time="readableTime"
+            />
+          </span>
+        </span>
         <i
           v-if="isPrivate"
           v-tooltip.top-start="toolTipMessage"
@@ -71,10 +75,16 @@ export default {
     isBubble() {
       return [0, 1, 3].includes(this.data.message_type);
     },
+    hasAttachments() {
+      return !!(this.data.attachments && this.data.attachments.length > 0);
+    },
     hasImageAttachment() {
-      const { attachment = {} } = this.data;
-      const { file_type: fileType } = attachment;
-      return fileType === 'image';
+      if (this.hasAttachments && this.data.attachments.length > 0) {
+        const { attachments = [{}] } = this.data;
+        const { file_type: fileType } = attachments[0];
+        return fileType === 'image';
+      }
+      return false;
     },
     isPrivate() {
       return this.data.private;
diff --git a/app/javascript/dashboard/helper/actionCable.js b/app/javascript/dashboard/helper/actionCable.js
index 27ff80dbc..38500f16b 100644
--- a/app/javascript/dashboard/helper/actionCable.js
+++ b/app/javascript/dashboard/helper/actionCable.js
@@ -6,6 +6,7 @@ class ActionCableConnector extends BaseActionCableConnector {
     super(app, pubsubToken);
     this.events = {
       'message.created': this.onMessageCreated,
+      'message.updated': this.onMessageUpdated,
       'conversation.created': this.onConversationCreated,
       'status_change:conversation': this.onStatusChange,
       'user:logout': this.onLogout,
@@ -14,6 +15,10 @@ class ActionCableConnector extends BaseActionCableConnector {
     };
   }
 
+  onMessageUpdated = data => {
+    this.app.$store.dispatch('updateMessage', data);
+  };
+
   onAssigneeChanged = payload => {
     const { meta = {}, id } = payload;
     const { assignee } = meta || {};
diff --git a/app/javascript/dashboard/store/modules/conversations/actions.js b/app/javascript/dashboard/store/modules/conversations/actions.js
index df299fabc..c770c6a46 100644
--- a/app/javascript/dashboard/store/modules/conversations/actions.js
+++ b/app/javascript/dashboard/store/modules/conversations/actions.js
@@ -145,6 +145,10 @@ const actions = {
     commit(types.default.ADD_MESSAGE, message);
   },
 
+  updateMessage({ commit }, message) {
+    commit(types.default.ADD_MESSAGE, message);
+  },
+
   addConversation({ commit }, conversation) {
     commit(types.default.ADD_CONVERSATION, conversation);
   },
@@ -192,7 +196,7 @@ const actions = {
 
   sendAttachment: async ({ commit }, data) => {
     try {
-      const response = MessageApi.sendAttachment(data);
+      const response = await MessageApi.sendAttachment(data);
       commit(types.default.SEND_MESSAGE, response.data);
     } catch (error) {
       // Handle error
diff --git a/app/javascript/dashboard/store/modules/conversations/index.js b/app/javascript/dashboard/store/modules/conversations/index.js
index 317be297b..f61c3add4 100644
--- a/app/javascript/dashboard/store/modules/conversations/index.js
+++ b/app/javascript/dashboard/store/modules/conversations/index.js
@@ -122,12 +122,13 @@ const mutations = {
     _state.selectedChat.status = status;
   },
 
-  [types.default.SEND_MESSAGE](_state, data) {
+  [types.default.SEND_MESSAGE](_state, currentMessage) {
     const [chat] = getSelectedChatConversation(_state);
-    const previousMessageIds = chat.messages.map(m => m.id);
-    if (!previousMessageIds.includes(data.id)) {
-      chat.messages.push(data);
-    }
+    const allMessagesExceptCurrent = (chat.messages || []).filter(
+      message => message.id !== currentMessage.id
+    );
+    allMessagesExceptCurrent.push(currentMessage);
+    chat.messages = allMessagesExceptCurrent;
   },
 
   [types.default.ADD_MESSAGE](_state, message) {
@@ -135,12 +136,16 @@ const mutations = {
       c => c.id === message.conversation_id
     );
     if (!chat) return;
-    const previousMessageIds = chat.messages.map(m => m.id);
-    if (!previousMessageIds.includes(message.id)) {
+    const previousMessageIndex = chat.messages.findIndex(
+      m => m.id === message.id
+    );
+    if (previousMessageIndex === -1) {
       chat.messages.push(message);
       if (_state.selectedChat.id === message.conversation_id) {
         window.bus.$emit('scrollToMessage');
       }
+    } else {
+      chat.messages[previousMessageIndex] = message;
     }
   },
 
diff --git a/app/javascript/widget/api/conversation.js b/app/javascript/widget/api/conversation.js
index 542d8a213..3bacc3a36 100755
--- a/app/javascript/widget/api/conversation.js
+++ b/app/javascript/widget/api/conversation.js
@@ -8,7 +8,7 @@ const sendMessageAPI = async content => {
 };
 
 const sendAttachmentAPI = async attachment => {
-  const urlData = endPoints.sendAttachmnet(attachment);
+  const urlData = endPoints.sendAttachment(attachment);
   const result = await API.post(urlData.url, urlData.params);
   return result;
 };
diff --git a/app/javascript/widget/api/endPoints.js b/app/javascript/widget/api/endPoints.js
index 4cc4cf726..c86f915e4 100755
--- a/app/javascript/widget/api/endPoints.js
+++ b/app/javascript/widget/api/endPoints.js
@@ -9,14 +9,13 @@ const sendMessage = content => ({
   },
 });
 
-const sendAttachmnet = ({ attachment }) => {
+const sendAttachment = ({ attachment }) => {
   const { refererURL = '' } = window;
   const timestamp = new Date().toString();
-  const { file, file_type: fileType } = attachment;
+  const { file } = attachment;
 
   const formData = new FormData();
-  formData.append('message[attachment][file]', file);
-  formData.append('message[attachment][file_type]', fileType);
+  formData.append('message[attachments][]', file, file.name);
   formData.append('message[referer_url]', refererURL);
   formData.append('message[timestamp]', timestamp);
   return {
@@ -43,7 +42,7 @@ const getAvailableAgents = token => ({
 
 export default {
   sendMessage,
-  sendAttachmnet,
+  sendAttachment,
   getConversation,
   updateMessage,
   getAvailableAgents,
diff --git a/app/javascript/widget/components/AgentMessage.vue b/app/javascript/widget/components/AgentMessage.vue
index 0341e46af..31f33d190 100755
--- a/app/javascript/widget/components/AgentMessage.vue
+++ b/app/javascript/widget/components/AgentMessage.vue
@@ -11,26 +11,26 @@
       </div>
       <div class="message-wrap">
         <AgentMessageBubble
-          v-if="showTextBubble && shouldDisplayAgentMessage"
+          v-if="!hasAttachments && shouldDisplayAgentMessage"
           :content-type="contentType"
           :message-content-attributes="messageContentAttributes"
           :message-id="message.id"
           :message-type="messageType"
           :message="message.content"
         />
-        <div v-if="hasAttachment" class="chat-bubble has-attachment agent">
-          <file-bubble
-            v-if="
-              message.attachment && message.attachment.file_type !== 'image'
-            "
-            :url="message.attachment.data_url"
-          />
-          <image-bubble
-            v-else
-            :url="message.attachment.data_url"
-            :thumb="message.attachment.thumb_url"
-            :readable-time="readableTime"
-          />
+        <div v-if="hasAttachments" class="chat-bubble has-attachment agent">
+          <div v-for="attachment in message.attachments" :key="attachment.id">
+            <file-bubble
+              v-if="attachment.file_type !== 'image'"
+              :url="attachment.data_url"
+            />
+            <image-bubble
+              v-else
+              :url="attachment.data_url"
+              :thumb="attachment.thumb_url"
+              :readable-time="readableTime"
+            />
+          </div>
         </div>
         <p v-if="message.showAvatar || hasRecordedResponse" class="agent-name">
           {{ agentName }}
@@ -78,12 +78,10 @@ export default {
       }
       return true;
     },
-    hasAttachment() {
-      return !!this.message.attachment;
-    },
-    showTextBubble() {
-      const { message } = this;
-      return !message.attachment;
+    hasAttachments() {
+      return !!(
+        this.message.attachments && this.message.attachments.length > 0
+      );
     },
     readableTime() {
       const { created_at: createdAt = '' } = this.message;
diff --git a/app/javascript/widget/components/ImageBubble.vue b/app/javascript/widget/components/ImageBubble.vue
index e81661c63..02078398b 100644
--- a/app/javascript/widget/components/ImageBubble.vue
+++ b/app/javascript/widget/components/ImageBubble.vue
@@ -47,6 +47,7 @@ export default {
 
   img {
     width: 100%;
+    max-width: 250px;
   }
 
   .time {
diff --git a/app/javascript/widget/components/UserMessage.vue b/app/javascript/widget/components/UserMessage.vue
index a07f9b05b..578a9b939 100755
--- a/app/javascript/widget/components/UserMessage.vue
+++ b/app/javascript/widget/components/UserMessage.vue
@@ -6,18 +6,20 @@
         :message="message.content"
         :status="message.status"
       />
-      <div v-if="hasAttachment" class="chat-bubble has-attachment user">
-        <file-bubble
-          v-if="message.attachment && message.attachment.file_type !== 'image'"
-          :url="message.attachment.data_url"
-          :is-in-progress="isInProgress"
-        />
-        <image-bubble
-          v-else
-          :url="message.attachment.data_url"
-          :thumb="message.attachment.thumb_url"
-          :readable-time="readableTime"
-        />
+      <div v-if="hasAttachments" class="chat-bubble has-attachment user">
+        <div v-for="attachment in message.attachments" :key="attachment.id">
+          <file-bubble
+            v-if="attachment.file_type !== 'image'"
+            :url="attachment.data_url"
+            :is-in-progress="isInProgress"
+          />
+          <image-bubble
+            v-else
+            :url="attachment.data_url"
+            :thumb="attachment.thumb_url"
+            :readable-time="readableTime"
+          />
+        </div>
       </div>
     </div>
   </div>
@@ -48,8 +50,10 @@ export default {
       const { status = '' } = this.message;
       return status === 'in_progress';
     },
-    hasAttachment() {
-      return !!this.message.attachment;
+    hasAttachments() {
+      return !!(
+        this.message.attachments && this.message.attachments.length > 0
+      );
     },
     showTextBubble() {
       const { message } = this;
diff --git a/app/javascript/widget/helpers/actionCable.js b/app/javascript/widget/helpers/actionCable.js
index a7706bbe5..1518fb6bb 100644
--- a/app/javascript/widget/helpers/actionCable.js
+++ b/app/javascript/widget/helpers/actionCable.js
@@ -5,12 +5,17 @@ class ActionCableConnector extends BaseActionCableConnector {
     super(app, pubsubToken);
     this.events = {
       'message.created': this.onMessageCreated,
+      'message.updated': this.onMessageUpdated,
     };
   }
 
   onMessageCreated = data => {
     this.app.$store.dispatch('conversation/addMessage', data);
   };
+
+  onMessageUpdated = data => {
+    this.app.$store.dispatch('conversation/updateMessage', data);
+  };
 }
 
 export const refreshActionCableConnector = pubsubToken => {
diff --git a/app/javascript/widget/store/modules/conversation.js b/app/javascript/widget/store/modules/conversation.js
index 3a7762a42..c33c84b9c 100755
--- a/app/javascript/widget/store/modules/conversation.js
+++ b/app/javascript/widget/store/modules/conversation.js
@@ -12,12 +12,12 @@ import DateHelper from '../../../shared/helpers/DateHelper';
 
 const groupBy = require('lodash.groupby');
 
-export const createTemporaryMessage = ({ attachment, content }) => {
+export const createTemporaryMessage = ({ attachments, content }) => {
   const timestamp = new Date().getTime() / 1000;
   return {
     id: getUuid(),
     content,
-    attachment,
+    attachments,
     status: 'in_progress',
     created_at: timestamp,
     message_type: MESSAGE_TYPE.INCOMING,
@@ -97,11 +97,14 @@ export const actions = {
       file_type: fileType,
       status: 'in_progress',
     };
-    const tempMessage = createTemporaryMessage({ attachment });
+    const tempMessage = createTemporaryMessage({ attachments: [attachment] });
     commit('pushMessageToConversation', tempMessage);
     try {
       const { data } = await sendAttachmentAPI(params);
-      commit('setMessageStatus', { message: data, tempId: tempMessage.id });
+      commit('updateAttachmentMessageStatus', {
+        message: data,
+        tempId: tempMessage.id,
+      });
     } catch (error) {
       // Show error
     }
@@ -125,6 +128,10 @@ export const actions = {
 
     commit('pushMessageToConversation', data);
   },
+
+  updateMessage({ commit }, data) {
+    commit('pushMessageToConversation', data);
+  },
 };
 
 export const mutations = {
@@ -151,24 +158,15 @@ export const mutations = {
     }
   },
 
-  setMessageStatus($state, { message, tempId }) {
-    const { status, id } = message;
+  updateAttachmentMessageStatus($state, { message, tempId }) {
+    const { id } = message;
     const messagesInbox = $state.conversations;
 
     const messageInConversation = messagesInbox[tempId];
 
     if (messageInConversation) {
       Vue.delete(messagesInbox, tempId);
-      const { attachment } = messageInConversation;
-      if (attachment.file_type === 'file') {
-        attachment.data_url = message.attachment.data_url;
-      }
-      Vue.set(messagesInbox, id, {
-        ...messageInConversation,
-        attachment,
-        id,
-        status,
-      });
+      Vue.set(messagesInbox, id, { ...message });
     }
   },
 
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 1cf371e89..87dad5eda 100644
--- a/app/javascript/widget/store/modules/specs/conversation/actions.spec.js
+++ b/app/javascript/widget/store/modules/specs/conversation/actions.spec.js
@@ -26,6 +26,13 @@ describe('#actions', () => {
     });
   });
 
+  describe('#updateMessage', () => {
+    it('sends correct mutations', () => {
+      actions.updateMessage({ commit }, { id: 1 });
+      expect(commit).toBeCalledWith('pushMessageToConversation', { id: 1 });
+    });
+  });
+
   describe('#sendMessage', () => {
     it('sends correct mutations', () => {
       const mockDate = new Date(1466424490000);
@@ -59,12 +66,14 @@ describe('#actions', () => {
         status: 'in_progress',
         created_at: 1466424490,
         message_type: 0,
-        attachment: {
-          thumb_url: '',
-          data_url: '',
-          file_type: 'file',
-          status: 'in_progress',
-        },
+        attachments: [
+          {
+            thumb_url: '',
+            data_url: '',
+            file_type: 'file',
+            status: 'in_progress',
+          },
+        ],
       });
     });
   });
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 3a99b509f..9f29b531b 100644
--- a/app/javascript/widget/store/modules/specs/conversation/mutations.spec.js
+++ b/app/javascript/widget/store/modules/specs/conversation/mutations.spec.js
@@ -93,7 +93,7 @@ describe('#mutations', () => {
     });
   });
 
-  describe('#setMessageStatus', () => {
+  describe('#updateAttachmentMessageStatus', () => {
     it('Updates status of loading messages if payload is not empty', () => {
       const state = {
         conversations: {
@@ -113,12 +113,18 @@ describe('#mutations', () => {
         id: '1',
         content: '',
         status: 'sent',
-        attachment: {
-          file: '',
-          file_type: 'image',
-        },
+        message_type: 0,
+        attachments: [
+          {
+            file: '',
+            file_type: 'image',
+          },
+        ],
       };
-      mutations.setMessageStatus(state, { message, tempId: 'rand_id_123' });
+      mutations.updateAttachmentMessageStatus(state, {
+        message,
+        tempId: 'rand_id_123',
+      });
 
       expect(state.conversations).toEqual({
         1: {
@@ -126,10 +132,12 @@ describe('#mutations', () => {
           content: '',
           message_type: 0,
           status: 'sent',
-          attachment: {
-            file: '',
-            file_type: 'image',
-          },
+          attachments: [
+            {
+              file: '',
+              file_type: 'image',
+            },
+          ],
         },
       });
     });
diff --git a/app/listeners/action_cable_listener.rb b/app/listeners/action_cable_listener.rb
index ca79ceba3..fc4e16960 100644
--- a/app/listeners/action_cable_listener.rb
+++ b/app/listeners/action_cable_listener.rb
@@ -22,6 +22,15 @@ class ActionCableListener < BaseListener
     send_to_contact(contact, MESSAGE_CREATED, message)
   end
 
+  def message_updated(event)
+    message, account, timestamp = extract_message_and_account(event)
+    conversation = message.conversation
+    contact = conversation.contact
+    members = conversation.inbox.members.pluck(:pubsub_token)
+    send_to_members(members, MESSAGE_UPDATED, message.push_event_data)
+    send_to_contact(contact, MESSAGE_UPDATED, message)
+  end
+
   def conversation_reopened(event)
     conversation, account, timestamp = extract_conversation_and_account(event)
     members = conversation.inbox.members.pluck(:pubsub_token)
diff --git a/app/models/message.rb b/app/models/message.rb
index cc323ebd0..218059537 100644
--- a/app/models/message.rb
+++ b/app/models/message.rb
@@ -35,6 +35,8 @@
 class Message < ApplicationRecord
   include Events::Types
 
+  NUMBER_OF_PERMITTED_ATTACHMENTS = 15
+
   validates :account_id, presence: true
   validates :inbox_id, presence: true
   validates :conversation_id, presence: true
@@ -65,7 +67,7 @@ class Message < ApplicationRecord
   belongs_to :user, required: false
   belongs_to :contact, required: false
 
-  has_one :attachment, dependent: :destroy, autosave: true
+  has_many :attachments, dependent: :destroy, autosave: true, before_add: :validate_attachments_limit
 
   after_create :reopen_conversation,
                :dispatch_event,
@@ -85,7 +87,7 @@ class Message < ApplicationRecord
       message_type: message_type_before_type_cast,
       conversation_id: conversation.display_id
     )
-    data.merge!(attachment: attachment.push_event_data) if attachment
+    data.merge!(attachments: attachments.map(&:push_event_data)) if attachments.present?
     data.merge!(sender: user.push_event_data) if user
     data
   end
@@ -159,4 +161,8 @@ class Message < ApplicationRecord
       ConversationReplyEmailWorker.perform_in(2.minutes, conversation.id, Time.zone.now)
     end
   end
+
+  def validate_attachments_limit(_attachment)
+    errors.add(attachments: 'exceeded maximum allowed') if attachments.size >= NUMBER_OF_PERMITTED_ATTACHMENTS
+  end
 end
diff --git a/app/services/facebook/send_reply_service.rb b/app/services/facebook/send_reply_service.rb
index 87e07fe8c..df897a1f2 100644
--- a/app/services/facebook/send_reply_service.rb
+++ b/app/services/facebook/send_reply_service.rb
@@ -46,7 +46,7 @@ class Facebook::SendReplyService
         attachment: {
           type: 'image',
           payload: {
-            url: message.attachment.file_url
+            url: message.attachments.first.file_url
           }
         }
       }
@@ -54,7 +54,7 @@ class Facebook::SendReplyService
   end
 
   def fb_message_params
-    if message.attachment.blank?
+    if message.attachments.blank?
       fb_text_message_params
     else
       fb_attachment_message_params
diff --git a/app/views/api/v1/accounts/conversations/messages/create.json.jbuilder b/app/views/api/v1/accounts/conversations/messages/create.json.jbuilder
index e01408e43..0dc5b827e 100644
--- a/app/views/api/v1/accounts/conversations/messages/create.json.jbuilder
+++ b/app/views/api/v1/accounts/conversations/messages/create.json.jbuilder
@@ -7,4 +7,4 @@ json.content_type @message.content_type
 json.content_attributes @message.content_attributes
 json.created_at @message.created_at.to_i
 json.private @message.private
-json.attachment @message.attachment.push_event_data if @message.attachment
+json.attachments @message.attachments.map(&:push_event_data) if @message.attachments.present?
diff --git a/app/views/api/v1/accounts/conversations/messages/index.json.jbuilder b/app/views/api/v1/accounts/conversations/messages/index.json.jbuilder
index f9b88c36c..64333d3ec 100644
--- a/app/views/api/v1/accounts/conversations/messages/index.json.jbuilder
+++ b/app/views/api/v1/accounts/conversations/messages/index.json.jbuilder
@@ -14,7 +14,7 @@ json.payload do
     json.created_at message.created_at.to_i
     json.private message.private
     json.source_id message.source_id
-    json.attachment message.attachment.push_event_data if message.attachment
+    json.attachments message.attachments.map(&:push_event_data) if message.attachments.present?
     json.sender message.user.push_event_data if message.user
   end
 end
diff --git a/app/views/api/v1/widget/messages/create.json.jbuilder b/app/views/api/v1/widget/messages/create.json.jbuilder
index 051a911e7..ff442b304 100644
--- a/app/views/api/v1/widget/messages/create.json.jbuilder
+++ b/app/views/api/v1/widget/messages/create.json.jbuilder
@@ -6,5 +6,5 @@ json.message_type @message.message_type_before_type_cast
 json.created_at @message.created_at.to_i
 json.private @message.private
 json.source_id @message.source_id
-json.attachment @message.attachment.push_event_data if @message.attachment
+json.attachments @message.attachments.map(&:push_event_data) if @message.attachments.present?
 json.sender @message.user.push_event_data if @message.user
diff --git a/app/views/api/v1/widget/messages/index.json.jbuilder b/app/views/api/v1/widget/messages/index.json.jbuilder
index c39ed54b8..f6491991c 100644
--- a/app/views/api/v1/widget/messages/index.json.jbuilder
+++ b/app/views/api/v1/widget/messages/index.json.jbuilder
@@ -6,6 +6,6 @@ json.array! @messages do |message|
   json.content_attributes message.content_attributes
   json.created_at message.created_at.to_i
   json.conversation_id message.conversation.display_id
-  json.attachment message.attachment.push_event_data if message.attachment
+  json.attachments message.attachments.map(&:push_event_data) if message.attachments.present?
   json.sender message.user.push_event_data if message.user
 end
diff --git a/app/views/mailers/conversation_reply_mailer/reply_with_summary.html.erb b/app/views/mailers/conversation_reply_mailer/reply_with_summary.html.erb
index 51e486380..5a490de62 100644
--- a/app/views/mailers/conversation_reply_mailer/reply_with_summary.html.erb
+++ b/app/views/mailers/conversation_reply_mailer/reply_with_summary.html.erb
@@ -9,11 +9,14 @@
         <b><%= message.incoming? ? 'You' : message.user.name %></b>
       </td>
       <td>:
-        <% if message.attachment %>
-          attachment [<a href="<%= message.attachment.file_url %>" _target="blank">click here to view</a>]
-        <% else %>
+        <% if message.content %>
           <%= message.content %>
         <% end %>
+        <% if message.attachments %>
+          <% message.attachments.each do |attachment| %>
+            attachment [<a href="<%= attachment.file_url %>" _target="blank">click here to view</a>]
+          <% end %>
+        <% end %>
       </td>
     </tr>
   <% end %>
diff --git a/docs/development/environment-setup/mac-os.md b/docs/development/environment-setup/mac-os.md
index 36321ebc6..860291e79 100644
--- a/docs/development/environment-setup/mac-os.md
+++ b/docs/development/environment-setup/mac-os.md
@@ -99,11 +99,14 @@ launchctl unload ~/Library/LaunchAgents/homebrew.mxcl.redis.plist
 ```
 
 ### Install imagemagick
+Chatwoot uses `imagemagick` library to resize images for showing previews and smaller size based on context.
 
 ```bash
 brew install imagemagick
 ```
 
+You can read more on installing imagemagick from source from [here](https://imagemagick.org/script/download.php).
+
 ### Install Docker
 
 This is an optional step. Those who are doing development can install docker from [Docker Desktop](https://www.docker.com/products/docker-desktop).
diff --git a/spec/controllers/api/v1/accounts/conversations/messages_controller_spec.rb b/spec/controllers/api/v1/accounts/conversations/messages_controller_spec.rb
index 588a129ab..6137a7298 100644
--- a/spec/controllers/api/v1/accounts/conversations/messages_controller_spec.rb
+++ b/spec/controllers/api/v1/accounts/conversations/messages_controller_spec.rb
@@ -33,15 +33,15 @@ RSpec.describe 'Conversation Messages API', type: :request do
 
       it 'creates a new outgoing message with attachment' do
         file = fixture_file_upload(Rails.root.join('spec/assets/avatar.png'), 'image/png')
-        params = { content: 'test-message', attachment: { file: file } }
+        params = { content: 'test-message', attachments: [file] }
 
         post api_v1_account_conversation_messages_url(account_id: account.id, conversation_id: conversation.display_id),
              params: params,
              headers: agent.create_new_auth_token
 
         expect(response).to have_http_status(:success)
-        expect(conversation.messages.last.attachment.file.present?).to eq(true)
-        expect(conversation.messages.last.attachment.file_type).to eq('image')
+        expect(conversation.messages.last.attachments.first.file.present?).to eq(true)
+        expect(conversation.messages.last.attachments.first.file_type).to eq('image')
       end
     end
 
diff --git a/spec/controllers/api/v1/widget/messages_controller_spec.rb b/spec/controllers/api/v1/widget/messages_controller_spec.rb
index 8ce37e17a..62c374295 100644
--- a/spec/controllers/api/v1/widget/messages_controller_spec.rb
+++ b/spec/controllers/api/v1/widget/messages_controller_spec.rb
@@ -47,7 +47,7 @@ RSpec.describe '/api/v1/widget/messages', type: :request do
 
       it 'creates attachment message in conversation' do
         file = fixture_file_upload(Rails.root.join('spec/assets/avatar.png'), 'image/png')
-        message_params = { content: 'hello world', timestamp: Time.current, attachment: { file: file } }
+        message_params = { content: 'hello world', timestamp: Time.current, attachments: [file] }
         post api_v1_widget_messages_url,
              params: { website_token: web_widget.website_token, message: message_params },
              headers: { 'X-Auth-Token' => token }
@@ -56,8 +56,8 @@ RSpec.describe '/api/v1/widget/messages', type: :request do
         json_response = JSON.parse(response.body)
         expect(json_response['content']).to eq(message_params[:content])
 
-        expect(conversation.messages.last.attachment.file.present?).to eq(true)
-        expect(conversation.messages.last.attachment.file_type).to eq('image')
+        expect(conversation.messages.last.attachments.first.file.present?).to eq(true)
+        expect(conversation.messages.last.attachments.first.file_type).to eq('image')
       end
     end
   end
diff --git a/spec/services/facebook/send_reply_service_spec.rb b/spec/services/facebook/send_reply_service_spec.rb
index 11aea9d58..74a06f237 100644
--- a/spec/services/facebook/send_reply_service_spec.rb
+++ b/spec/services/facebook/send_reply_service_spec.rb
@@ -50,8 +50,8 @@ describe Facebook::SendReplyService do
       it 'if message with attachment is sent from chatwoot and is outgoing' do
         create(:message, message_type: :incoming, inbox: facebook_inbox, account: account, conversation: conversation)
         message = build(:message, message_type: 'outgoing', inbox: facebook_inbox, account: account, conversation: conversation)
-        message.attachment = Attachment.new(account_id: message.account_id, file_type: :image)
-        message.attachment.file.attach(io: File.open(Rails.root.join('spec/assets/avatar.png')), filename: 'avatar.png', content_type: 'image/png')
+        attachment = message.attachments.new(account_id: message.account_id, file_type: :image)
+        attachment.file.attach(io: File.open(Rails.root.join('spec/assets/avatar.png')), filename: 'avatar.png', content_type: 'image/png')
         message.save!
         expect(bot).to have_received(:deliver)
       end