diff --git a/app/javascript/dashboard/assets/scss/widgets/_modal.scss b/app/javascript/dashboard/assets/scss/widgets/_modal.scss
index c363d4220..cc22dc778 100644
--- a/app/javascript/dashboard/assets/scss/widgets/_modal.scss
+++ b/app/javascript/dashboard/assets/scss/widgets/_modal.scss
@@ -86,6 +86,12 @@
       margin-left: var(--space-small);
     }
 
+    &:first-child {
+      .button {
+        margin-left: 0;
+      }
+    }
+
     &.justify-content-end {
       justify-content: end;
     }
diff --git a/app/javascript/dashboard/components/ui/ContextMenu.vue b/app/javascript/dashboard/components/ui/ContextMenu.vue
index b968cda19..6d8fca703 100644
--- a/app/javascript/dashboard/components/ui/ContextMenu.vue
+++ b/app/javascript/dashboard/components/ui/ContextMenu.vue
@@ -1,7 +1,5 @@
 <template>
   <div
-    v-show="show"
-    ref="context"
     class="context-menu-container"
     :style="style"
     tabindex="0"
@@ -39,7 +37,6 @@ export default {
   },
   mounted() {
     this.$nextTick(() => this.$el.focus());
-    this.show = true;
   },
 };
 </script>
diff --git a/app/javascript/dashboard/components/widgets/conversation/Message.vue b/app/javascript/dashboard/components/widgets/conversation/Message.vue
index 0a876872f..612039c68 100644
--- a/app/javascript/dashboard/components/widgets/conversation/Message.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/Message.vue
@@ -1,6 +1,6 @@
 <template>
   <li v-if="shouldRenderMessage" :class="alignBubble">
-    <div :class="wrapClass">
+    <div :class="wrapClass" @contextmenu="openContextMenu($event)">
       <div v-tooltip.top-start="messageToolTip" :class="bubbleClass">
         <bubble-mail-head
           :email-attributes="contentAttributes.email"
@@ -73,12 +73,6 @@
           :created-at="createdAt"
         />
       </div>
-      <translate-modal
-        v-if="showTranslateModal"
-        :content="data.content"
-        :content-attributes="contentAttributes"
-        @close="onCloseTranslateModal"
-      />
       <spinner v-if="isPending" size="tiny" />
       <div
         v-if="showAvatar"
@@ -114,15 +108,12 @@
     <div v-if="shouldShowContextMenu" class="context-menu-wrap">
       <context-menu
         v-if="isBubble && !isMessageDeleted"
+        :context-menu-position="contextMenuPosition"
         :is-open="showContextMenu"
-        :show-copy="hasText"
-        :show-delete="hasText || hasAttachments"
-        :show-canned-response-option="isOutgoing && hasText"
-        :menu-position="contextMenuPosition"
-        :message-content="data.content"
-        @toggle="handleContextMenuClick"
-        @delete="handleDelete"
-        @translate="handleTranslate"
+        :enabled-options="contextMenuEnabledOptions"
+        :message="data"
+        @open="openContextMenu"
+        @close="closeContextMenu"
       />
     </div>
   </li>
@@ -145,8 +136,8 @@ import alertMixin from 'shared/mixins/alertMixin';
 import contentTypeMixin from 'shared/mixins/contentTypeMixin';
 import { MESSAGE_TYPE, MESSAGE_STATUS } from 'shared/constants/messages';
 import { generateBotMessageContent } from './helpers/botMessageContentHelper';
-import { mapGetters } from 'vuex';
-import TranslateModal from './bubble/TranslateModal.vue';
+import { BUS_EVENTS } from 'shared/constants/busEvents';
+import { ACCOUNT_EVENTS } from 'dashboard/helper/AnalyticsHelper/events';
 
 export default {
   components: {
@@ -162,7 +153,6 @@ export default {
     ContextMenu,
     Spinner,
     instagramImageErrorPlaceholder,
-    TranslateModal,
   },
   mixins: [alertMixin, messageFormatterMixin, contentTypeMixin],
   props: {
@@ -191,14 +181,10 @@ export default {
     return {
       showContextMenu: false,
       hasImageError: false,
-      showTranslateModal: false,
+      contextMenuPosition: {},
     };
   },
   computed: {
-    ...mapGetters({
-      getAccount: 'accounts/getAccount',
-      currentAccountId: 'getCurrentAccountId',
-    }),
     shouldRenderMessage() {
       return (
         this.hasAttachments ||
@@ -256,6 +242,13 @@ export default {
         ) + botMessageContent
       );
     },
+    contextMenuEnabledOptions() {
+      return {
+        copy: this.hasText,
+        delete: this.hasText || this.hasAttachments,
+        cannedResponse: this.isOutgoing && this.hasText,
+      };
+    },
     contentAttributes() {
       return this.data.content_attributes || {};
     },
@@ -384,10 +377,6 @@ export default {
       if (this.isPending || this.isFailed) return false;
       return !this.sender.type || this.sender.type === 'agent_bot';
     },
-    contextMenuPosition() {
-      const { message_type: messageType } = this.data;
-      return messageType ? 'right' : 'left';
-    },
     shouldShowContextMenu() {
       return !(this.isFailed || this.isPending);
     },
@@ -416,6 +405,10 @@ export default {
   },
   mounted() {
     this.hasImageError = false;
+    bus.$on(BUS_EVENTS.ON_MESSAGE_LIST_SCROLL, this.closeContextMenu);
+  },
+  beforeDestroy() {
+    bus.$off(BUS_EVENTS.ON_MESSAGE_LIST_SCROLL, this.closeContextMenu);
   },
   methods: {
     hasMediaAttachment(type) {
@@ -429,37 +422,29 @@ export default {
     handleContextMenuClick() {
       this.showContextMenu = !this.showContextMenu;
     },
-    async handleDelete() {
-      const { conversation_id: conversationId, id: messageId } = this.data;
-      try {
-        await this.$store.dispatch('deleteMessage', {
-          conversationId,
-          messageId,
-        });
-        this.showAlert(this.$t('CONVERSATION.SUCCESS_DELETE_MESSAGE'));
-        this.showContextMenu = false;
-      } catch (error) {
-        this.showAlert(this.$t('CONVERSATION.FAIL_DELETE_MESSSAGE'));
-      }
-    },
     async retrySendMessage() {
       await this.$store.dispatch('sendMessageWithData', this.data);
     },
     onImageLoadError() {
       this.hasImageError = true;
     },
-    handleTranslate() {
-      const { locale } = this.getAccount(this.currentAccountId);
-      const { conversation_id: conversationId, id: messageId } = this.data;
-      this.$store.dispatch('translateMessage', {
-        conversationId,
-        messageId,
-        targetLanguage: locale || 'en',
-      });
-      this.showTranslateModal = true;
+    openContextMenu(e) {
+      if (getSelection().toString()) {
+        return;
+      }
+      e.preventDefault();
+      if (e.type === 'contextmenu') {
+        this.$track(ACCOUNT_EVENTS.OPEN_MESSAGE_CONTEXT_MENU);
+      }
+      this.contextMenuPosition = {
+        x: e.pageX || e.clientX,
+        y: e.pageY || e.clientY,
+      };
+      this.showContextMenu = true;
     },
-    onCloseTranslateModal() {
-      this.showTranslateModal = false;
+    closeContextMenu() {
+      this.showContextMenu = false;
+      this.contextMenuPosition = { x: null, y: null };
     },
   },
 };
diff --git a/app/javascript/dashboard/components/widgets/conversation/MessagesView.vue b/app/javascript/dashboard/components/widgets/conversation/MessagesView.vue
index dad2b28a0..a11ed206b 100644
--- a/app/javascript/dashboard/components/widgets/conversation/MessagesView.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/MessagesView.vue
@@ -355,6 +355,7 @@ export default {
     },
 
     handleScroll(e) {
+      bus.$emit(BUS_EVENTS.ON_MESSAGE_LIST_SCROLL);
       this.setScrollParams();
 
       const dataFetchCheck =
diff --git a/app/javascript/dashboard/helper/AnalyticsHelper/events.js b/app/javascript/dashboard/helper/AnalyticsHelper/events.js
index 0ffccd668..f8615a30c 100644
--- a/app/javascript/dashboard/helper/AnalyticsHelper/events.js
+++ b/app/javascript/dashboard/helper/AnalyticsHelper/events.js
@@ -13,6 +13,7 @@ export const ACCOUNT_EVENTS = Object.freeze({
   ADDED_TO_CANNED_RESPONSE: 'Used added to canned response option',
   ADDED_A_CUSTOM_ATTRIBUTE: 'Added a custom attribute',
   ADDED_AN_INBOX: 'Added an inbox',
+  OPEN_MESSAGE_CONTEXT_MENU: 'Opened message context menu',
 });
 
 export const LABEL_EVENTS = Object.freeze({
diff --git a/app/javascript/dashboard/i18n/locale/en/conversation.json b/app/javascript/dashboard/i18n/locale/en/conversation.json
index f98a3cdc0..5eb562d83 100644
--- a/app/javascript/dashboard/i18n/locale/en/conversation.json
+++ b/app/javascript/dashboard/i18n/locale/en/conversation.json
@@ -166,7 +166,13 @@
       "COPY": "Copy",
       "DELETE": "Delete",
       "CREATE_A_CANNED_RESPONSE": "Add to canned responses",
-      "TRANSLATE": "Translate"
+      "TRANSLATE": "Translate",
+      "DELETE_CONFIRMATION": {
+        "TITLE": "Are you sure you want to delete this message?",
+        "MESSAGE": "You cannot undo this action",
+        "DELETE": "Delete",
+        "CANCEL": "Cancel"
+      }
     }
   },
   "EMAIL_TRANSCRIPT": {
diff --git a/app/javascript/dashboard/modules/conversations/components/MessageContextMenu.vue b/app/javascript/dashboard/modules/conversations/components/MessageContextMenu.vue
index d3b98bcac..7462dd4f1 100644
--- a/app/javascript/dashboard/modules/conversations/components/MessageContextMenu.vue
+++ b/app/javascript/dashboard/modules/conversations/components/MessageContextMenu.vue
@@ -1,7 +1,8 @@
 <template>
   <div class="context-menu">
+    <!-- Add To Canned Responses -->
     <woot-modal
-      v-if="isCannedResponseModalOpen && showCannedResponseOption"
+      v-if="isCannedResponseModalOpen && enabledOptions['cannedResponse']"
       :show.sync="isCannedResponseModalOpen"
       :on-close="hideCannedResponseModal"
     >
@@ -10,156 +11,229 @@
         :on-close="hideCannedResponseModal"
       />
     </woot-modal>
+    <!-- Translate Content -->
+    <translate-modal
+      v-if="showTranslateModal"
+      :content="messageContent"
+      :content-attributes="contentAttributes"
+      @close="onCloseTranslateModal"
+    />
+    <!-- Confirm Deletion -->
+    <woot-delete-modal
+      v-if="showDeleteModal"
+      class="context-menu--delete-modal"
+      :show.sync="showDeleteModal"
+      :on-close="closeDeleteModal"
+      :on-confirm="confirmDeletion"
+      :title="$t('CONVERSATION.CONTEXT_MENU.DELETE_CONFIRMATION.TITLE')"
+      :message="$t('CONVERSATION.CONTEXT_MENU.DELETE_CONFIRMATION.MESSAGE')"
+      :confirm-text="$t('CONVERSATION.CONTEXT_MENU.DELETE_CONFIRMATION.DELETE')"
+      :reject-text="$t('CONVERSATION.CONTEXT_MENU.DELETE_CONFIRMATION.CANCEL')"
+    />
     <woot-button
       icon="more-vertical"
       color-scheme="secondary"
       variant="clear"
       size="small"
-      @click="handleContextMenuClick"
+      @click="handleOpen"
     />
-    <div
+    <woot-context-menu
       v-if="isOpen && !isCannedResponseModalOpen"
-      v-on-clickaway="handleContextMenuClick"
-      class="dropdown-pane dropdown-pane--open"
-      :class="`dropdown-pane--${menuPosition}`"
+      :x="contextMenuPosition.x"
+      :y="contextMenuPosition.y"
+      @close="handleClose"
     >
-      <woot-dropdown-menu>
-        <woot-dropdown-item v-if="showDelete">
-          <woot-button
-            variant="clear"
-            color-scheme="alert"
-            size="small"
-            icon="delete"
-            @click="handleDelete"
-          >
-            {{ $t('CONVERSATION.CONTEXT_MENU.DELETE') }}
-          </woot-button>
-        </woot-dropdown-item>
-        <woot-dropdown-item v-if="showCopy">
-          <woot-button
-            variant="clear"
-            size="small"
-            icon="clipboard"
-            color-scheme="secondary"
-            @click="handleCopy"
-          >
-            {{ $t('CONVERSATION.CONTEXT_MENU.COPY') }}
-          </woot-button>
-        </woot-dropdown-item>
-        <woot-dropdown-item v-if="showCannedResponseOption">
-          <woot-button
-            variant="clear"
-            size="small"
-            icon="comment-add"
-            color-scheme="secondary"
-            @click="showCannedResponseModal"
-          >
-            {{ $t('CONVERSATION.CONTEXT_MENU.CREATE_A_CANNED_RESPONSE') }}
-          </woot-button>
-        </woot-dropdown-item>
-        <woot-dropdown-item>
-          <woot-button
-            variant="clear"
-            size="small"
-            icon="translate"
-            color-scheme="secondary"
-            @click="handleTranslate"
-          >
-            {{ $t('CONVERSATION.CONTEXT_MENU.TRANSLATE') }}
-          </woot-button>
-        </woot-dropdown-item>
-      </woot-dropdown-menu>
-    </div>
+      <div class="menu-container">
+        <menu-item
+          v-if="enabledOptions['copy']"
+          :option="{
+            icon: 'clipboard',
+            label: this.$t('CONVERSATION.CONTEXT_MENU.COPY'),
+          }"
+          variant="icon"
+          @click="handleCopy"
+        />
+        <menu-item
+          :option="{
+            icon: 'translate',
+            label: this.$t('CONVERSATION.CONTEXT_MENU.TRANSLATE'),
+          }"
+          variant="icon"
+          @click="handleTranslate"
+        />
+        <hr v-if="enabledOptions['cannedResponse']" />
+        <menu-item
+          v-if="enabledOptions['cannedResponse']"
+          :option="{
+            icon: 'comment-add',
+            label: this.$t(
+              'CONVERSATION.CONTEXT_MENU.CREATE_A_CANNED_RESPONSE'
+            ),
+          }"
+          variant="icon"
+          @click="showCannedResponseModal"
+        />
+        <hr v-if="enabledOptions['delete']" />
+        <menu-item
+          v-if="enabledOptions['delete']"
+          :option="{
+            icon: 'delete',
+            label: this.$t('CONVERSATION.CONTEXT_MENU.DELETE'),
+          }"
+          variant="icon"
+          @click="openDeleteModal"
+        />
+      </div>
+    </woot-context-menu>
   </div>
 </template>
 <script>
 import alertMixin from 'shared/mixins/alertMixin';
+import { mapGetters } from 'vuex';
 import { mixin as clickaway } from 'vue-clickaway';
 import messageFormatterMixin from 'shared/mixins/messageFormatterMixin';
-
 import AddCannedModal from 'dashboard/routes/dashboard/settings/canned/AddCanned';
-import WootDropdownItem from 'shared/components/ui/dropdown/DropdownItem';
-import WootDropdownMenu from 'shared/components/ui/dropdown/DropdownMenu';
 import { copyTextToClipboard } from 'shared/helpers/clipboard';
 import { ACCOUNT_EVENTS } from '../../../helper/AnalyticsHelper/events';
+import TranslateModal from 'dashboard/components/widgets/conversation/bubble/TranslateModal';
+import MenuItem from '../../../components/widgets/conversation/contextMenu/menuItem.vue';
 
 export default {
   components: {
     AddCannedModal,
-    WootDropdownMenu,
-    WootDropdownItem,
+    TranslateModal,
+    MenuItem,
   },
   mixins: [alertMixin, clickaway, messageFormatterMixin],
   props: {
-    messageContent: {
-      type: String,
-      default: '',
+    message: {
+      type: Object,
+      required: true,
     },
     isOpen: {
       type: Boolean,
       default: false,
     },
-    showCopy: {
-      type: Boolean,
-      default: false,
+    enabledOptions: {
+      type: Object,
+      default: () => ({}),
     },
-    showDelete: {
-      type: Boolean,
-      default: false,
-    },
-    menuPosition: {
-      type: String,
-      default: 'left',
-    },
-    showCannedResponseOption: {
-      type: Boolean,
-      default: true,
+    contextMenuPosition: {
+      type: Object,
+      default: () => ({}),
     },
   },
   data() {
-    return { isCannedResponseModalOpen: false };
+    return {
+      isCannedResponseModalOpen: false,
+      showTranslateModal: false,
+      showDeleteModal: false,
+    };
   },
   computed: {
+    ...mapGetters({
+      getAccount: 'accounts/getAccount',
+      currentAccountId: 'getCurrentAccountId',
+    }),
     plainTextContent() {
       return this.getPlainText(this.messageContent);
     },
+    conversationId() {
+      return this.message.conversation_id;
+    },
+    messageId() {
+      return this.message.id;
+    },
+    messageContent() {
+      return this.message.content;
+    },
+    contentAttributes() {
+      return this.message.content_attributes;
+    },
   },
   methods: {
-    handleContextMenuClick() {
-      this.$emit('toggle', !this.isOpen);
-    },
     async handleCopy() {
       await copyTextToClipboard(this.plainTextContent);
       this.showAlert(this.$t('CONTACT_PANEL.COPY_SUCCESSFUL'));
-      this.$emit('toggle', false);
-    },
-    handleDelete() {
-      this.$emit('delete');
-    },
-    hideCannedResponseModal() {
-      this.isCannedResponseModalOpen = false;
-      this.$emit('toggle', false);
+      this.handleClose();
     },
     showCannedResponseModal() {
       this.$track(ACCOUNT_EVENTS.ADDED_TO_CANNED_RESPONSE);
       this.isCannedResponseModalOpen = true;
     },
-
+    hideCannedResponseModal() {
+      this.isCannedResponseModalOpen = false;
+      this.handleClose();
+    },
+    handleOpen(e) {
+      this.$emit('open', e);
+    },
+    handleClose(e) {
+      this.$emit('close', e);
+    },
     handleTranslate() {
-      this.$emit('translate');
-      this.handleContextMenuClick();
+      const { locale } = this.getAccount(this.currentAccountId);
+      this.$store.dispatch('translateMessage', {
+        conversationId: this.conversationId,
+        messageId: this.messageId,
+        targetLanguage: locale || 'en',
+      });
+      this.handleClose();
+      this.showTranslateModal = true;
+    },
+    onCloseTranslateModal() {
+      this.showTranslateModal = false;
+    },
+
+    openDeleteModal() {
+      this.handleClose();
+      this.showDeleteModal = true;
+    },
+    async confirmDeletion() {
+      try {
+        await this.$store.dispatch('deleteMessage', {
+          conversationId: this.conversationId,
+          messageId: this.messageId,
+        });
+        this.showAlert(this.$t('CONVERSATION.SUCCESS_DELETE_MESSAGE'));
+        this.handleClose();
+      } catch (error) {
+        this.showAlert(this.$t('CONVERSATION.FAIL_DELETE_MESSSAGE'));
+      }
+    },
+    closeDeleteModal() {
+      this.showDeleteModal = false;
     },
   },
 };
 </script>
 <style lang="scss" scoped>
-.dropdown-pane {
-  bottom: var(--space-large);
+.menu-container {
+  padding: var(--space-smaller);
+  background-color: var(--white);
+  box-shadow: var(--shadow-context-menu);
+  border-radius: var(--border-radius-normal);
+
+  hr {
+    border-bottom: 1px solid var(--color-border-light);
+    margin: var(--space-smaller);
+  }
 }
-.dropdown-pane--left {
-  right: var(--space-minus-small);
-}
-.dropdown-pane--right {
-  left: var(--space-minus-small);
+
+.context-menu--delete-modal {
+  ::v-deep {
+    .modal-container {
+      max-width: 48rem;
+
+      h2 {
+        font-weight: var(--font-weight-medium);
+        font-size: var(--font-size-default);
+      }
+    }
+
+    .modal-footer {
+      padding: var(--space-normal) var(--space-large) var(--space-large);
+    }
+  }
 }
 </style>
diff --git a/app/javascript/shared/constants/busEvents.js b/app/javascript/shared/constants/busEvents.js
index a1f1b1f07..0c446afea 100644
--- a/app/javascript/shared/constants/busEvents.js
+++ b/app/javascript/shared/constants/busEvents.js
@@ -6,4 +6,5 @@ export const BUS_EVENTS = {
   SCROLL_TO_MESSAGE: 'SCROLL_TO_MESSAGE',
   TOGGLE_SIDEMENU: 'TOGGLE_SIDEMENU',
   WEBSOCKET_DISCONNECT: 'WEBSOCKET_DISCONNECT',
+  ON_MESSAGE_LIST_SCROLL: 'ON_MESSAGE_LIST_SCROLL',
 };