diff --git a/src/components/AnchorForCommentsOnly/BaseAnchorForCommentsOnly/index.js b/src/components/AnchorForCommentsOnly/BaseAnchorForCommentsOnly/index.js
index 4683d9534e7a..dab9d2ea718f 100644
--- a/src/components/AnchorForCommentsOnly/BaseAnchorForCommentsOnly/index.js
+++ b/src/components/AnchorForCommentsOnly/BaseAnchorForCommentsOnly/index.js
@@ -10,6 +10,7 @@ import * as ReportActionContextMenu from '../../../pages/home/report/ContextMenu
 import * as ContextMenuActions from '../../../pages/home/report/ContextMenu/ContextMenuActions';
 import AttachmentView from '../../AttachmentView';
 import fileDownload from '../../../libs/fileDownload';
+import Tooltip from '../../Tooltip';
 import canUseTouchScreen from '../../../libs/canUseTouchscreen';
 import styles from '../../../styles/styles';
 
@@ -74,20 +75,22 @@ class BaseAnchorForCommentsOnly extends React.Component {
                         }
                     }
                     >
-                        <Text
-                            ref={el => linkRef = el}
-                            style={StyleSheet.flatten([this.props.style, defaultTextStyle])}
-                            accessibilityRole="link"
-                            href={this.props.href}
-                            hrefAttrs={{
-                                rel: this.props.rel,
-                                target: this.props.target,
-                            }}
-                        // eslint-disable-next-line react/jsx-props-no-spreading
-                            {...rest}
-                        >
-                            {this.props.children}
-                        </Text>
+                        <Tooltip text={Str.isValidEmail(this.props.displayName) ? '' : this.props.href}>
+                            <Text
+                                ref={el => linkRef = el}
+                                style={StyleSheet.flatten([this.props.style, defaultTextStyle])}
+                                accessibilityRole="link"
+                                href={this.props.href}
+                                hrefAttrs={{
+                                    rel: this.props.rel,
+                                    target: this.props.target,
+                                }}
+                            // eslint-disable-next-line react/jsx-props-no-spreading
+                                {...rest}
+                            >
+                                {this.props.children}
+                            </Text>
+                        </Tooltip>
                     </PressableWithSecondaryInteraction>
                 )
         );
diff --git a/src/components/ContextMenuItem.js b/src/components/ContextMenuItem.js
index 58b361fca823..339e36afd6eb 100644
--- a/src/components/ContextMenuItem.js
+++ b/src/components/ContextMenuItem.js
@@ -29,6 +29,9 @@ const propTypes = {
 
     /** Automatically reset the success status */
     autoReset: PropTypes.bool,
+
+    /** A description text to show under the title */
+    description: PropTypes.string,
 };
 
 const defaultProps = {
@@ -36,6 +39,7 @@ const defaultProps = {
     successIcon: null,
     successText: '',
     autoReset: false,
+    description: '',
 };
 
 class ContextMenuItem extends Component {
@@ -109,6 +113,7 @@ class ContextMenuItem extends Component {
                         onPress={this.triggerPressAndUpdateSuccess}
                         wrapperStyle={styles.pr9}
                         success={this.state.success}
+                        description={this.props.description}
                     />
                 )
         );
diff --git a/src/components/MenuItem.js b/src/components/MenuItem.js
index 6c5c20eb008e..9e40683893ba 100644
--- a/src/components/MenuItem.js
+++ b/src/components/MenuItem.js
@@ -59,7 +59,7 @@ const MenuItem = props => (
     >
         {({hovered, pressed}) => (
             <>
-                <View style={[styles.flexRow, styles.pointerEventsNone]}>
+                <View style={[styles.flexRow, styles.pointerEventsNone, styles.flex1]}>
                     {(props.icon && props.iconType === CONST.ICON_TYPE_ICON) && (
                         <View
                             style={[
@@ -90,7 +90,7 @@ const MenuItem = props => (
                             />
                         </View>
                     )}
-                    <View style={[styles.justifyContentCenter, styles.menuItemTextContainer]}>
+                    <View style={[styles.justifyContentCenter, styles.menuItemTextContainer, styles.flex1]}>
                         <Text
                             style={[
                                 styles.popoverMenuText,
@@ -101,8 +101,11 @@ const MenuItem = props => (
                         >
                             {props.title}
                         </Text>
-                        {props.description && (
-                            <Text style={[styles.textLabelSupporting, styles.ml3, styles.mt1]}>
+                        {Boolean(props.description) && (
+                            <Text
+                                style={[styles.textLabelSupporting, styles.ml3, styles.mt1, styles.breakAll]}
+                                numberOfLines={2}
+                            >
                                 {props.description}
                             </Text>
                         )}
diff --git a/src/pages/home/report/ContextMenu/BaseReportActionContextMenu.js b/src/pages/home/report/ContextMenu/BaseReportActionContextMenu.js
index 98bcc5dca80d..ea0b478aaf63 100755
--- a/src/pages/home/report/ContextMenu/BaseReportActionContextMenu.js
+++ b/src/pages/home/report/ContextMenu/BaseReportActionContextMenu.js
@@ -10,12 +10,15 @@ import {
 } from './genericReportActionContextMenuPropTypes';
 import withLocalize, {withLocalizePropTypes} from '../../../../components/withLocalize';
 import ContextMenuActions, {CONTEXT_MENU_TYPES} from './ContextMenuActions';
+import compose from '../../../../libs/compose';
+import withWindowDimensions, {windowDimensionsPropTypes} from '../../../../components/withWindowDimensions';
 
 const propTypes = {
     /** String representing the context menu type [LINK, REPORT_ACTION] which controls context menu choices  */
     type: PropTypes.string,
     ...genericReportActionContextMenuPropTypes,
     ...withLocalizePropTypes,
+    ...windowDimensionsPropTypes,
 };
 
 const defaultProps = {
@@ -49,6 +52,7 @@ class BaseReportActionContextMenu extends React.Component {
                             draftMessage: this.props.draftMessage,
                             selection: this.props.selection,
                         })}
+                        description={contextAction.getDescription(this.props.selection, this.props.isSmallScreenWidth)}
                     />
                 ))}
             </View>
@@ -59,4 +63,7 @@ class BaseReportActionContextMenu extends React.Component {
 BaseReportActionContextMenu.propTypes = propTypes;
 BaseReportActionContextMenu.defaultProps = defaultProps;
 
-export default withLocalize(BaseReportActionContextMenu);
+export default compose(
+    withLocalize,
+    withWindowDimensions,
+)(BaseReportActionContextMenu);
diff --git a/src/pages/home/report/ContextMenu/ContextMenuActions.js b/src/pages/home/report/ContextMenu/ContextMenuActions.js
index 099ee746b9c9..ec14d63b88b5 100644
--- a/src/pages/home/report/ContextMenu/ContextMenuActions.js
+++ b/src/pages/home/report/ContextMenu/ContextMenuActions.js
@@ -11,6 +11,7 @@ import CONST from '../../../../CONST';
 import getAttachmentDetails from '../../../../libs/fileDownload/getAttachmentDetails';
 import fileDownload from '../../../../libs/fileDownload';
 import addEncryptedAuthTokenToURL from '../../../../libs/addEncryptedAuthTokenToURL';
+import * as ContextMenuUtils from './ContextMenuUtils';
 
 /**
  * Gets the HTML version of the message in an action.
@@ -51,6 +52,7 @@ export default [
             sourceURL = addEncryptedAuthTokenToURL(sourceURL);
             fileDownload(sourceURL, originalFileName);
         },
+        getDescription: () => {},
     },
     {
         textTranslateKey: 'reportActionContextMenu.copyURLToClipboard',
@@ -62,6 +64,7 @@ export default [
             Clipboard.setString(selection);
             hideContextMenu(true, ReportActionComposeFocusManager.focus);
         },
+        getDescription: ContextMenuUtils.getPopoverDescription,
     },
     {
         textTranslateKey: 'reportActionContextMenu.copyEmailToClipboard',
@@ -73,6 +76,7 @@ export default [
             Clipboard.setString(selection.replace('mailto:', ''));
             hideContextMenu(true, ReportActionComposeFocusManager.focus);
         },
+        getDescription: () => {},
     },
     {
         textTranslateKey: 'reportActionContextMenu.copyToClipboard',
@@ -107,6 +111,7 @@ export default [
                 hideContextMenu(true, ReportActionComposeFocusManager.focus);
             }
         },
+        getDescription: () => {},
     },
 
     {
@@ -114,6 +119,7 @@ export default [
         icon: Expensicons.LinkCopy,
         shouldShow: () => false,
         onPress: () => {},
+        getDescription: () => {},
     },
 
     {
@@ -128,6 +134,7 @@ export default [
                 hideContextMenu(true, ReportActionComposeFocusManager.focus);
             }
         },
+        getDescription: () => {},
     },
 
     {
@@ -152,6 +159,7 @@ export default [
             // No popover to hide, call editAction immediately
             editAction();
         },
+        getDescription: () => {},
     },
     {
         textTranslateKey: 'reportActionContextMenu.deleteComment',
@@ -171,6 +179,7 @@ export default [
             // No popover to hide, call showDeleteConfirmModal immediately
             showDeleteModal(reportID, reportAction);
         },
+        getDescription: () => {},
     },
 ];
 
diff --git a/src/pages/home/report/ContextMenu/ContextMenuUtils/index.js b/src/pages/home/report/ContextMenu/ContextMenuUtils/index.js
new file mode 100644
index 000000000000..f694f413e29a
--- /dev/null
+++ b/src/pages/home/report/ContextMenu/ContextMenuUtils/index.js
@@ -0,0 +1,17 @@
+/* eslint-disable import/prefer-default-export */
+
+/**
+ * The popover description will be an empty string on anything but mobile web
+ * because we show link in tooltip instead of popover on web
+ *
+ * @param {String} selection
+ * @param {Boolean} isSmallScreenWidth
+ * @returns {String}
+ */
+function getPopoverDescription(selection, isSmallScreenWidth) {
+    return isSmallScreenWidth ? selection : '';
+}
+
+export {
+    getPopoverDescription,
+};
diff --git a/src/pages/home/report/ContextMenu/ContextMenuUtils/index.native.js b/src/pages/home/report/ContextMenu/ContextMenuUtils/index.native.js
new file mode 100644
index 000000000000..3dbf81926098
--- /dev/null
+++ b/src/pages/home/report/ContextMenu/ContextMenuUtils/index.native.js
@@ -0,0 +1,15 @@
+/* eslint-disable import/prefer-default-export */
+
+/**
+ * Always show popover description on native platforms
+ *
+ * @param {String} selection
+ * @returns {String}
+ */
+function getPopoverDescription(selection) {
+    return selection;
+}
+
+export {
+    getPopoverDescription,
+};
diff --git a/src/pages/home/report/ContextMenu/PopoverReportActionContextMenu.js b/src/pages/home/report/ContextMenu/PopoverReportActionContextMenu.js
index bb2668573d70..b77599ad9bea 100644
--- a/src/pages/home/report/ContextMenu/PopoverReportActionContextMenu.js
+++ b/src/pages/home/report/ContextMenu/PopoverReportActionContextMenu.js
@@ -285,7 +285,7 @@ class PopoverReportActionContextMenu extends React.Component {
                     animationOutTiming={1}
                     measureContent={this.measureContent}
                     shouldSetModalVisibility={false}
-                    fullscreen={false}
+                    fullscreen
                 >
                     <BaseReportActionContextMenu
                         isVisible