diff --git a/app/helpers/file_type_helper.rb b/app/helpers/file_type_helper.rb
index 64d67701a..503c7f25b 100644
--- a/app/helpers/file_type_helper.rb
+++ b/app/helpers/file_type_helper.rb
@@ -1,16 +1,29 @@
 module FileTypeHelper
+  # NOTE: video, audio, image, etc are filetypes previewable in frontend
   def file_type(content_type)
-    return :image if [
-      'image/jpeg',
-      'image/png',
-      'image/gif',
-      'image/tiff',
-      'image/bmp'
-    ].include?(content_type)
-
-    return :video if content_type.include?('video/')
+    return :image if image_file?(content_type)
+    return :video if video_file?(content_type)
     return :audio if content_type.include?('audio/')
 
     :file
   end
+
+  def image_file?(content_type)
+    [
+      'image/jpeg',
+      'image/png',
+      'image/gif',
+      'image/bmp',
+      'image/webp'
+    ].include?(content_type)
+  end
+
+  def video_file?(content_type)
+    [
+      'video/ogg',
+      'video/mp4',
+      'video/webm',
+      'video/quicktime'
+    ].include?(content_type)
+  end
 end
diff --git a/app/javascript/dashboard/assets/scss/_foundation-settings.scss b/app/javascript/dashboard/assets/scss/_foundation-settings.scss
index 13b7dfafd..c6b7f6fd3 100644
--- a/app/javascript/dashboard/assets/scss/_foundation-settings.scss
+++ b/app/javascript/dashboard/assets/scss/_foundation-settings.scss
@@ -45,6 +45,9 @@
 // 1. Global
 // ---------
 
+// Disable contrast warnings in Foundation.
+$contrast-warnings: false;
+
 $global-font-size: 10px;
 $global-width: 100%;
 $global-lineheight: 1.5;
diff --git a/app/javascript/dashboard/components/widgets/WootWriter/ReplyBottomPanel.vue b/app/javascript/dashboard/components/widgets/WootWriter/ReplyBottomPanel.vue
index 5b47648d1..594aaa6aa 100644
--- a/app/javascript/dashboard/components/widgets/WootWriter/ReplyBottomPanel.vue
+++ b/app/javascript/dashboard/components/widgets/WootWriter/ReplyBottomPanel.vue
@@ -15,7 +15,7 @@
       <file-upload
         ref="upload"
         :size="4096 * 4096"
-        accept="image/png, image/jpeg, image/gif, image/bmp, image/tiff, application/pdf, audio/mpeg, video/mp4, audio/ogg, text/csv"
+        :accept="allowedFileTypes"
         :drop="true"
         :drop-directory="false"
         @input-file="onFileUpload"
@@ -84,6 +84,7 @@ import {
   hasPressedAltAndAKey,
 } from 'shared/helpers/KeyboardHelpers';
 import eventListenerMixins from 'shared/mixins/eventListenerMixins';
+import { ALLOWED_FILE_TYPES } from 'shared/constants/messages';
 
 import { REPLY_EDITOR_MODES } from './constants';
 export default {
@@ -161,6 +162,9 @@ export default {
     showAttachButton() {
       return this.showFileUpload || this.isNote;
     },
+    allowedFileTypes() {
+      return ALLOWED_FILE_TYPES;
+    },
   },
   methods: {
     handleKeyEvents(e) {
diff --git a/app/javascript/dashboard/components/widgets/conversation/Message.vue b/app/javascript/dashboard/components/widgets/conversation/Message.vue
index 5d04199e1..0612783bb 100644
--- a/app/javascript/dashboard/components/widgets/conversation/Message.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/Message.vue
@@ -24,9 +24,10 @@
         <div v-if="!isPending && hasAttachments">
           <div v-for="attachment in data.attachments" :key="attachment.id">
             <bubble-image
-              v-if="attachment.file_type === 'image'"
+              v-if="attachment.file_type === 'image' && !hasImageError"
               :url="attachment.data_url"
               :readable-time="readableTime"
+              @error="onImageLoadError"
             />
             <audio v-else-if="attachment.file_type === 'audio'" controls>
               <source :src="attachment.data_url" />
@@ -133,6 +134,7 @@ export default {
   data() {
     return {
       showContextMenu: false,
+      hasImageError: false,
     };
   },
   computed: {
@@ -287,12 +289,20 @@ export default {
       return messageType ? 'right' : 'left';
     },
   },
+  watch: {
+    data() {
+      this.hasImageError = false;
+    },
+  },
+  mounted() {
+    this.hasImageError = false;
+  },
   methods: {
     hasMediaAttachment(type) {
       if (this.hasAttachments && this.data.attachments.length > 0) {
         const { attachments = [{}] } = this.data;
         const { file_type: fileType } = attachments[0];
-        return fileType === type;
+        return fileType === type && !this.hasImageError;
       }
       return false;
     },
@@ -317,6 +327,9 @@ export default {
       this.showAlert(this.$t('CONTACT_PANEL.COPY_SUCCESSFUL'));
       this.showContextMenu = false;
     },
+    onImageLoadError() {
+      this.hasImageError = true;
+    },
   },
 };
 </script>
diff --git a/app/javascript/dashboard/components/widgets/conversation/bubble/Image.vue b/app/javascript/dashboard/components/widgets/conversation/bubble/Image.vue
index 124ce09c9..828b8059b 100644
--- a/app/javascript/dashboard/components/widgets/conversation/bubble/Image.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/bubble/Image.vue
@@ -1,6 +1,6 @@
 <template>
   <div class="image message-text__wrap">
-    <img :src="url" @click="onClick" />
+    <img :src="url" @click="onClick" @error="onImgError()" />
     <woot-modal :full-width="true" :show.sync="show" :on-close="onClose">
       <img :src="url" class="modal-image" />
     </woot-modal>
@@ -9,6 +9,7 @@
 
 <script>
 export default {
+  components: {},
   props: {
     url: {
       type: String,
@@ -27,6 +28,9 @@ export default {
     onClick() {
       this.show = true;
     },
+    onImgError() {
+      this.$emit('error');
+    },
   },
 };
 </script>
diff --git a/app/javascript/dashboard/routes/dashboard/settings/inbox/Settings.vue b/app/javascript/dashboard/routes/dashboard/settings/inbox/Settings.vue
index ac54dac85..cb61c2f97 100644
--- a/app/javascript/dashboard/routes/dashboard/settings/inbox/Settings.vue
+++ b/app/javascript/dashboard/routes/dashboard/settings/inbox/Settings.vue
@@ -32,7 +32,11 @@
           :label="inboxNameLabel"
           :placeholder="inboxNamePlaceHolder"
         />
-        <label for="toggle-business-hours" class="toggle-input-wrap" v-if="isATwitterInbox">
+        <label
+          v-if="isATwitterInbox"
+          for="toggle-business-hours"
+          class="toggle-input-wrap"
+        >
           <input
             v-model="tweetsEnabled"
             type="checkbox"
diff --git a/app/javascript/shared/constants/messages.js b/app/javascript/shared/constants/messages.js
index f9d7cb332..16bd332fa 100644
--- a/app/javascript/shared/constants/messages.js
+++ b/app/javascript/shared/constants/messages.js
@@ -13,6 +13,17 @@ export const MESSAGE_TYPE = {
 // Size in mega bytes
 export const MAXIMUM_FILE_UPLOAD_SIZE = 40;
 
+export const ALLOWED_FILE_TYPES =
+  'image/*,' +
+  'audio/*,' +
+  'video/*,' +
+  '.3gpp,' +
+  'text/csv, text/plain, application/json, application/pdf, text/rtf,' +
+  'application/zip, application/x-7z-compressed application/vnd.rar application/x-tar,' +
+  'application/msword, application/vnd.ms-excel, application/vnd.ms-powerpoint, application/vnd.oasis.opendocument.text,' +
+  'application/vnd.openxmlformats-officedocument.presentationml.presentation, application/vnd.openxmlformats-officedocument.spreadsheetml.sheet,' +
+  'application/vnd.openxmlformats-officedocument.wordprocessingml.document,';
+
 export const CSAT_RATINGS = [
   {
     key: 'disappointed',
diff --git a/app/javascript/widget/components/ChatAttachment.vue b/app/javascript/widget/components/ChatAttachment.vue
index e33c3812e..501c1bcb2 100755
--- a/app/javascript/widget/components/ChatAttachment.vue
+++ b/app/javascript/widget/components/ChatAttachment.vue
@@ -1,7 +1,7 @@
 <template>
   <file-upload
     :size="4096 * 2048"
-    accept="image/*, application/pdf, audio/mpeg, video/mp4, audio/ogg, text/csv"
+    :accept="allowedFileTypes"
     @input-file="onFileUpload"
   >
     <button class="icon-button flex items-center justify-center">
@@ -15,7 +15,10 @@
 import FileUpload from 'vue-upload-component';
 import Spinner from 'shared/components/Spinner.vue';
 import { checkFileSizeLimit } from 'shared/helpers/FileHelper';
-import { MAXIMUM_FILE_UPLOAD_SIZE } from 'shared/constants/messages';
+import {
+  MAXIMUM_FILE_UPLOAD_SIZE,
+  ALLOWED_FILE_TYPES,
+} from 'shared/constants/messages';
 import { BUS_EVENTS } from 'shared/constants/busEvents';
 import FluentIcon from 'shared/components/FluentIcon/Index.vue';
 export default {
@@ -33,6 +36,9 @@ export default {
     fileUploadSizeLimit() {
       return MAXIMUM_FILE_UPLOAD_SIZE;
     },
+    allowedFileTypes() {
+      return ALLOWED_FILE_TYPES;
+    },
   },
   methods: {
     getFileType(fileType) {
diff --git a/app/models/attachment.rb b/app/models/attachment.rb
index 0db94b9ba..cea0721b8 100644
--- a/app/models/attachment.rb
+++ b/app/models/attachment.rb
@@ -17,6 +17,18 @@
 
 class Attachment < ApplicationRecord
   include Rails.application.routes.url_helpers
+
+  ACCEPTABLE_FILE_TYPES = %w[
+    text/csv text/plain text/rtf
+    application/json application/pdf
+    application/zip application/x-7z-compressed application/vnd.rar application/x-tar
+    application/msword application/vnd.ms-excel application/vnd.ms-powerpoint application/rtf
+    application/vnd.oasis.opendocument.text
+    application/vnd.openxmlformats-officedocument.presentationml.presentation
+    application/vnd.openxmlformats-officedocument.spreadsheetml.sheet
+    application/vnd.openxmlformats-officedocument.wordprocessingml.document
+  ].freeze
+
   belongs_to :account
   belongs_to :message
   has_one_attached :file
@@ -90,10 +102,19 @@ class Attachment < ApplicationRecord
   def acceptable_file
     return unless should_validate_file?
 
-    errors.add(:file, 'is too big') if file.byte_size > 40.megabytes
+    validate_file_size(file.byte_size)
+    validate_file_content_type(file.content_type)
+  end
 
-    acceptable_types = ['image/png', 'image/jpeg', 'image/gif', 'image/bmp', 'image/tiff', 'application/pdf', 'audio/mpeg', 'video/mp4', 'audio/ogg',
-                        'text/csv'].freeze
-    errors.add(:file, 'filetype not supported') unless acceptable_types.include?(file.content_type)
+  def validate_file_content_type(file_content_type)
+    errors.add(:file, 'type not supported') unless media_file?(file_content_type) || ACCEPTABLE_FILE_TYPES.include?(file_content_type)
+  end
+
+  def validate_file_size(byte_size)
+    errors.add(:file, 'size is too big') if byte_size > 40.megabytes
+  end
+
+  def media_file?(file_content_type)
+    file_content_type.start_with?('image/', 'video/', 'audio/')
   end
 end