diff --git a/src/components/AnchorForAttachmentsOnly/BaseAnchorForAttachmentsOnly.js b/src/components/AnchorForAttachmentsOnly/BaseAnchorForAttachmentsOnly.js
index dec809e1266b..a1abfb0326f3 100644
--- a/src/components/AnchorForAttachmentsOnly/BaseAnchorForAttachmentsOnly.js
+++ b/src/components/AnchorForAttachmentsOnly/BaseAnchorForAttachmentsOnly.js
@@ -1,9 +1,30 @@
 import React from 'react';
 import {Pressable} from 'react-native';
-import * as anchorForAttachmentsOnlyPropTypes from './anchorForAttachmentsOnlyPropTypes';
+import PropTypes from 'prop-types';
+import {
+    propTypes as anchorForAttachmentsOnlyPropTypes,
+    defaultProps as anchorForAttachmentsOnlyDefaultProps,
+} from './anchorForAttachmentsOnlyPropTypes';
 import AttachmentView from '../AttachmentView';
 import fileDownload from '../../libs/fileDownload';
 import addEncryptedAuthTokenToURL from '../../libs/addEncryptedAuthTokenToURL';
+import {ShowContextMenuContext, showContextMenuForReport} from '../ShowContextMenuContext';
+
+const propTypes = {
+    /** Press in handler for the link */
+    onPressIn: PropTypes.func,
+
+    /** Press out handler for the link */
+    onPressOut: PropTypes.func,
+
+    ...anchorForAttachmentsOnlyPropTypes,
+};
+
+const defaultProps = {
+    onPressIn: undefined,
+    onPressOut: undefined,
+    ...anchorForAttachmentsOnlyDefaultProps,
+};
 
 class BaseAnchorForAttachmentsOnly extends React.Component {
     constructor(props) {
@@ -30,27 +51,45 @@ class BaseAnchorForAttachmentsOnly extends React.Component {
         const source = addEncryptedAuthTokenToURL(this.props.source);
 
         return (
-            <Pressable
-                style={this.props.style}
-                onPress={() => {
-                    if (this.state.isDownloading) {
-                        return;
-                    }
-                    this.processDownload(source, this.props.displayName);
-                }}
-            >
-                <AttachmentView
-                    sourceURL={source}
-                    file={{name: this.props.displayName}}
-                    shouldShowDownloadIcon
-                    shouldShowLoadingSpinnerIcon={this.state.isDownloading}
-                />
-            </Pressable>
+            <ShowContextMenuContext.Consumer>
+                {({
+                    anchor,
+                    reportID,
+                    action,
+                    checkIfContextMenuActive,
+                }) => (
+                    <Pressable
+                        style={this.props.style}
+                        onPress={() => {
+                            if (this.state.isDownloading) {
+                                return;
+                            }
+                            this.processDownload(source, this.props.displayName);
+                        }}
+                        onPressIn={this.props.onPressIn}
+                        onPressOut={this.props.onPressOut}
+                        onLongPress={event => showContextMenuForReport(
+                            event,
+                            anchor,
+                            reportID,
+                            action,
+                            checkIfContextMenuActive,
+                        )}
+                    >
+                        <AttachmentView
+                            sourceURL={source}
+                            file={{name: this.props.displayName}}
+                            shouldShowDownloadIcon
+                            shouldShowLoadingSpinnerIcon={this.state.isDownloading}
+                        />
+                    </Pressable>
+                )}
+            </ShowContextMenuContext.Consumer>
         );
     }
 }
 
-BaseAnchorForAttachmentsOnly.propTypes = anchorForAttachmentsOnlyPropTypes.propTypes;
-BaseAnchorForAttachmentsOnly.defaultProps = anchorForAttachmentsOnlyPropTypes.defaultProps;
+BaseAnchorForAttachmentsOnly.propTypes = propTypes;
+BaseAnchorForAttachmentsOnly.defaultProps = defaultProps;
 
 export default BaseAnchorForAttachmentsOnly;
diff --git a/src/components/AnchorForAttachmentsOnly/index.js b/src/components/AnchorForAttachmentsOnly/index.js
index a71d65e969cd..9a0fb4be1237 100644
--- a/src/components/AnchorForAttachmentsOnly/index.js
+++ b/src/components/AnchorForAttachmentsOnly/index.js
@@ -1,9 +1,17 @@
 import React from 'react';
 import * as anchorForAttachmentsOnlyPropTypes from './anchorForAttachmentsOnlyPropTypes';
 import BaseAnchorForAttachmentsOnly from './BaseAnchorForAttachmentsOnly';
+import * as DeviceCapabilities from '../../libs/DeviceCapabilities';
+import ControlSelection from '../../libs/ControlSelection';
 
-// eslint-disable-next-line react/jsx-props-no-spreading
-const AnchorForAttachmentsOnly = props => <BaseAnchorForAttachmentsOnly {...props} />;
+const AnchorForAttachmentsOnly = props => (
+    <BaseAnchorForAttachmentsOnly
+        // eslint-disable-next-line react/jsx-props-no-spreading
+        {...props}
+        onPressIn={() => DeviceCapabilities.canUseTouchScreen() && ControlSelection.block()}
+        onPressOut={() => ControlSelection.unblock()}
+    />
+);
 
 AnchorForAttachmentsOnly.propTypes = anchorForAttachmentsOnlyPropTypes.propTypes;
 AnchorForAttachmentsOnly.defaultProps = anchorForAttachmentsOnlyPropTypes.defaultProps;
diff --git a/src/components/AnchorForCommentsOnly/BaseAnchorForCommentsOnly.js b/src/components/AnchorForCommentsOnly/BaseAnchorForCommentsOnly.js
index e48e68e329f5..18d3fbf25960 100644
--- a/src/components/AnchorForCommentsOnly/BaseAnchorForCommentsOnly.js
+++ b/src/components/AnchorForCommentsOnly/BaseAnchorForCommentsOnly.js
@@ -1,6 +1,7 @@
 import _ from 'underscore';
 import React from 'react';
 import {StyleSheet} from 'react-native';
+import PropTypes from 'prop-types';
 import lodashGet from 'lodash/get';
 import Str from 'expensify-common/lib/str';
 import Text from '../Text';
@@ -11,13 +12,28 @@ import Tooltip from '../Tooltip';
 import * as DeviceCapabilities from '../../libs/DeviceCapabilities';
 import styles from '../../styles/styles';
 import withWindowDimensions, {windowDimensionsPropTypes} from '../withWindowDimensions';
-import {propTypes as anchorForCommentsOnlyPropTypes, defaultProps} from './anchorForCommentsOnlyPropTypes';
+import {
+    propTypes as anchorForCommentsOnlyPropTypes,
+    defaultProps as anchorForCommentsOnlyDefaultProps,
+} from './anchorForCommentsOnlyPropTypes';
 
 const propTypes = {
+    /** Press in handler for the link */
+    onPressIn: PropTypes.func,
+
+    /** Press out handler for the link */
+    onPressOut: PropTypes.func,
+
     ...anchorForCommentsOnlyPropTypes,
     ...windowDimensionsPropTypes,
 };
 
+const defaultProps = {
+    onPressIn: undefined,
+    onPressOut: undefined,
+    ...anchorForCommentsOnlyDefaultProps,
+};
+
 /*
  * This is a default anchor component for regular links.
  */
@@ -45,6 +61,9 @@ const BaseAnchorForCommentsOnly = (props) => {
                     );
                 }
             }
+            onPress={linkProps.onPress}
+            onPressIn={props.onPressIn}
+            onPressOut={props.onPressOut}
         >
             <Tooltip containerStyles={[styles.dInline]} text={Str.isValidEmail(props.displayName) ? '' : props.href}>
                 <Text
@@ -55,8 +74,7 @@ const BaseAnchorForCommentsOnly = (props) => {
                         rel: props.rel,
                         target: props.target,
                     }}
-                    // eslint-disable-next-line react/jsx-props-no-spreading
-                    {...linkProps}
+                    href={linkProps.href}
                     // eslint-disable-next-line react/jsx-props-no-spreading
                     {...rest}
                 >
diff --git a/src/components/AnchorForCommentsOnly/index.js b/src/components/AnchorForCommentsOnly/index.js
index 1526e78007fe..d25b819cddba 100644
--- a/src/components/AnchorForCommentsOnly/index.js
+++ b/src/components/AnchorForCommentsOnly/index.js
@@ -1,9 +1,18 @@
 import React from 'react';
 import * as anchorForCommentsOnlyPropTypes from './anchorForCommentsOnlyPropTypes';
 import BaseAnchorForCommentsOnly from './BaseAnchorForCommentsOnly';
+import * as DeviceCapabilities from '../../libs/DeviceCapabilities';
+import ControlSelection from '../../libs/ControlSelection';
+
+const AnchorForCommentsOnly = props => (
+    <BaseAnchorForCommentsOnly
+        // eslint-disable-next-line react/jsx-props-no-spreading
+        {...props}
+        onPressIn={() => DeviceCapabilities.canUseTouchScreen() && ControlSelection.block()}
+        onPressOut={() => ControlSelection.unblock()}
+    />
+);
 
-// eslint-disable-next-line react/jsx-props-no-spreading
-const AnchorForCommentsOnly = props => <BaseAnchorForCommentsOnly {...props} />;
 AnchorForCommentsOnly.propTypes = anchorForCommentsOnlyPropTypes.propTypes;
 AnchorForCommentsOnly.defaultProps = anchorForCommentsOnlyPropTypes.defaultProps;
 AnchorForCommentsOnly.displayName = 'AnchorForCommentsOnly';
diff --git a/src/components/HTMLEngineProvider/HTMLRenderers/ImageRenderer.js b/src/components/HTMLEngineProvider/HTMLRenderers/ImageRenderer.js
index f3e9009a72ca..cef91ba9a9e2 100644
--- a/src/components/HTMLEngineProvider/HTMLRenderers/ImageRenderer.js
+++ b/src/components/HTMLEngineProvider/HTMLRenderers/ImageRenderer.js
@@ -6,6 +6,7 @@ import styles from '../../../styles/styles';
 import ThumbnailImage from '../../ThumbnailImage';
 import PressableWithoutFocus from '../../PressableWithoutFocus';
 import CONST from '../../../CONST';
+import {ShowContextMenuContext, showContextMenuForReport} from '../../ShowContextMenuContext';
 
 const ImageRenderer = (props) => {
     const htmlAttribs = props.tnode.attributes;
@@ -57,27 +58,37 @@ const ImageRenderer = (props) => {
             imageHeight={imageHeight}
         />
     ) : (
-        <AttachmentModal
-            allowDownload
-            sourceURL={source}
-            isAuthTokenRequired={isAttachment}
-            originalFileName={originalFileName}
-        >
-            {({show}) => (
-                <PressableWithoutFocus
-                    style={styles.noOutline}
-                    onPress={show}
+        <ShowContextMenuContext.Consumer>
+            {({
+                anchor,
+                reportID,
+                action,
+                checkIfContextMenuActive,
+            }) => (
+                <AttachmentModal
+                    allowDownload
+                    sourceURL={source}
+                    isAuthTokenRequired={isAttachment}
+                    originalFileName={originalFileName}
                 >
-                    <ThumbnailImage
-                        previewSourceURL={previewSource}
-                        style={styles.webViewStyles.tagStyles.img}
-                        isAuthTokenRequired={isAttachment}
-                        imageWidth={imageWidth}
-                        imageHeight={imageHeight}
-                    />
-                </PressableWithoutFocus>
+                    {({show}) => (
+                        <PressableWithoutFocus
+                            style={styles.noOutline}
+                            onPress={show}
+                            onLongPress={event => showContextMenuForReport(event, anchor, reportID, action, checkIfContextMenuActive)}
+                        >
+                            <ThumbnailImage
+                                previewSourceURL={previewSource}
+                                style={styles.webViewStyles.tagStyles.img}
+                                isAuthTokenRequired={isAttachment}
+                                imageWidth={imageWidth}
+                                imageHeight={imageHeight}
+                            />
+                        </PressableWithoutFocus>
+                    )}
+                </AttachmentModal>
             )}
-        </AttachmentModal>
+        </ShowContextMenuContext.Consumer>
     );
 };
 
diff --git a/src/components/HTMLEngineProvider/HTMLRenderers/PreRenderer/BasePreRenderer.js b/src/components/HTMLEngineProvider/HTMLRenderers/PreRenderer/BasePreRenderer.js
index 5edafb4dc04d..25ea94e0ae6b 100644
--- a/src/components/HTMLEngineProvider/HTMLRenderers/PreRenderer/BasePreRenderer.js
+++ b/src/components/HTMLEngineProvider/HTMLRenderers/PreRenderer/BasePreRenderer.js
@@ -1,28 +1,59 @@
 import React, {forwardRef} from 'react';
 import {ScrollView} from 'react-native-gesture-handler';
-import {View} from 'react-native';
+import {Pressable} from 'react-native';
+import PropTypes from 'prop-types';
 import _ from 'underscore';
 import htmlRendererPropTypes from '../htmlRendererPropTypes';
 import withLocalize from '../../../withLocalize';
+import {ShowContextMenuContext, showContextMenuForReport} from '../../../ShowContextMenuContext';
+
+const propTypes = {
+    /** Press in handler for the code block */
+    onPressIn: PropTypes.func,
+
+    /** Press out handler for the code block */
+    onPressOut: PropTypes.func,
+
+    ...htmlRendererPropTypes,
+};
+
+const defaultProps = {
+    onPressIn: undefined,
+    onPressOut: undefined,
+};
 
 const BasePreRenderer = forwardRef((props, ref) => {
     const TDefaultRenderer = props.TDefaultRenderer;
-    const defaultRendererProps = _.omit(props, ['TDefaultRenderer']);
+    const defaultRendererProps = _.omit(props, ['TDefaultRenderer', 'onPressIn', 'onPressOut', 'onLongPress']);
 
     return (
         <ScrollView
             ref={ref}
             horizontal
         >
-            <View onStartShouldSetResponder={() => true}>
-                {/* eslint-disable-next-line react/jsx-props-no-spreading */}
-                <TDefaultRenderer {...defaultRendererProps} />
-            </View>
+            <ShowContextMenuContext.Consumer>
+                {({
+                    anchor,
+                    reportID,
+                    action,
+                    checkIfContextMenuActive,
+                }) => (
+                    <Pressable
+                        onPressIn={props.onPressIn}
+                        onPressOut={props.onPressOut}
+                        onLongPress={event => showContextMenuForReport(event, anchor, reportID, action, checkIfContextMenuActive)}
+                    >
+                        {/* eslint-disable-next-line react/jsx-props-no-spreading */}
+                        <TDefaultRenderer {...defaultRendererProps} />
+                    </Pressable>
+                )}
+            </ShowContextMenuContext.Consumer>
         </ScrollView>
     );
 });
 
 BasePreRenderer.displayName = 'BasePreRenderer';
-BasePreRenderer.propTypes = htmlRendererPropTypes;
+BasePreRenderer.propTypes = propTypes;
+BasePreRenderer.defaultProps = defaultProps;
 
 export default withLocalize(BasePreRenderer);
diff --git a/src/components/HTMLEngineProvider/HTMLRenderers/PreRenderer/index.js b/src/components/HTMLEngineProvider/HTMLRenderers/PreRenderer/index.js
index 59c05e73ed97..9e158ede05f0 100644
--- a/src/components/HTMLEngineProvider/HTMLRenderers/PreRenderer/index.js
+++ b/src/components/HTMLEngineProvider/HTMLRenderers/PreRenderer/index.js
@@ -3,6 +3,8 @@ import _ from 'underscore';
 import withLocalize from '../../../withLocalize';
 import htmlRendererPropTypes from '../htmlRendererPropTypes';
 import BasePreRenderer from './BasePreRenderer';
+import * as DeviceCapabilities from '../../../../libs/DeviceCapabilities';
+import ControlSelection from '../../../../libs/ControlSelection';
 
 class PreRenderer extends React.Component {
     constructor(props) {
@@ -58,6 +60,8 @@ class PreRenderer extends React.Component {
                 // eslint-disable-next-line react/jsx-props-no-spreading
                 {...this.props}
                 ref={el => this.ref = el}
+                onPressIn={() => DeviceCapabilities.canUseTouchScreen() && ControlSelection.block()}
+                onPressOut={() => ControlSelection.unblock()}
             />
         );
     }
diff --git a/src/components/PressableWithSecondaryInteraction/index.js b/src/components/PressableWithSecondaryInteraction/index.js
index d9e1629d33d6..7b971e726867 100644
--- a/src/components/PressableWithSecondaryInteraction/index.js
+++ b/src/components/PressableWithSecondaryInteraction/index.js
@@ -1,7 +1,6 @@
 import _ from 'underscore';
 import React, {Component} from 'react';
 import {Pressable} from 'react-native';
-import {LongPressGestureHandler, State} from 'react-native-gesture-handler';
 import * as pressableWithSecondaryInteractionPropTypes from './pressableWithSecondaryInteractionPropTypes';
 import styles from '../../styles/styles';
 import * as DeviceCapabilities from '../../libs/DeviceCapabilities';
@@ -12,7 +11,6 @@ import * as DeviceCapabilities from '../../libs/DeviceCapabilities';
 class PressableWithSecondaryInteraction extends Component {
     constructor(props) {
         super(props);
-        this.callSecondaryInteractionWithMappedEvent = this.callSecondaryInteractionWithMappedEvent.bind(this);
         this.executeSecondaryInteractionOnContextMenu = this.executeSecondaryInteractionOnContextMenu.bind(this);
     }
 
@@ -27,27 +25,6 @@ class PressableWithSecondaryInteraction extends Component {
         this.pressableRef.removeEventListener('contextmenu', this.executeSecondaryInteractionOnContextMenu);
     }
 
-    /**
-     * @param {Object} e
-     */
-    callSecondaryInteractionWithMappedEvent(e) {
-        if ((e.nativeEvent.state !== State.ACTIVE) || DeviceCapabilities.hasHoverSupport()) {
-            return;
-        }
-
-        // Map gesture event to normal Responder event
-        const {
-            absoluteX, absoluteY, locationX, locationY,
-        } = e.nativeEvent;
-        const mapEvent = {
-            ...e,
-            nativeEvent: {
-                ...e.nativeEvent, pageX: absoluteX, pageY: absoluteY, x: locationX, y: locationY,
-            },
-        };
-        this.props.onSecondaryInteraction(mapEvent);
-    }
-
     /**
      * @param {contextmenu} e - A right-click MouseEvent.
      * https://developer.mozilla.org/en-US/docs/Web/API/Element/contextmenu_event
@@ -65,19 +42,23 @@ class PressableWithSecondaryInteraction extends Component {
 
         // On Web, Text does not support LongPress events thus manage inline mode with styling instead of using Text.
         return (
-            <LongPressGestureHandler onHandlerStateChange={this.callSecondaryInteractionWithMappedEvent}>
-                <Pressable
-                    style={this.props.inline && styles.dInline}
-                    onPressIn={this.props.onPressIn}
-                    onPressOut={this.props.onPressOut}
-                    onPress={this.props.onPress}
-                    ref={el => this.pressableRef = el}
-                    // eslint-disable-next-line react/jsx-props-no-spreading
-                    {...defaultPressableProps}
-                >
-                    {this.props.children}
-                </Pressable>
-            </LongPressGestureHandler>
+            <Pressable
+                style={this.props.inline && styles.dInline}
+                onPressIn={this.props.onPressIn}
+                onLongPress={(e) => {
+                    if (DeviceCapabilities.hasHoverSupport()) {
+                        return;
+                    }
+                    this.props.onSecondaryInteraction(e);
+                }}
+                onPressOut={this.props.onPressOut}
+                onPress={this.props.onPress}
+                ref={el => this.pressableRef = el}
+                // eslint-disable-next-line react/jsx-props-no-spreading
+                {...defaultPressableProps}
+            >
+                {this.props.children}
+            </Pressable>
         );
     }
 }
diff --git a/src/components/PressableWithSecondaryInteraction/index.native.js b/src/components/PressableWithSecondaryInteraction/index.native.js
index 3b6edfc92198..f186146b4134 100644
--- a/src/components/PressableWithSecondaryInteraction/index.native.js
+++ b/src/components/PressableWithSecondaryInteraction/index.native.js
@@ -1,7 +1,6 @@
 import _ from 'underscore';
 import React, {forwardRef} from 'react';
 import {Pressable} from 'react-native';
-import {LongPressGestureHandler, State} from 'react-native-gesture-handler';
 import * as pressableWithSecondaryInteractionPropTypes from './pressableWithSecondaryInteractionPropTypes';
 import Text from '../Text';
 import HapticFeedback from '../../libs/HapticFeedback';
@@ -16,40 +15,21 @@ const PressableWithSecondaryInteraction = (props) => {
     // Use Text node for inline mode to prevent content overflow.
     const Node = props.inline ? Text : Pressable;
     return (
-        <LongPressGestureHandler
-            onHandlerStateChange={(e) => {
-                if (e.nativeEvent.state !== State.ACTIVE) {
-                    return;
-                }
-
-                // Map gesture event to normal Responder event
-                const {
-                    absoluteX, absoluteY, locationX, locationY,
-                } = e.nativeEvent;
-                const mapEvent = {
-                    ...e,
-                    nativeEvent: {
-                        ...e.nativeEvent, pageX: absoluteX, pageY: absoluteY, x: locationX, y: locationY,
-                    },
-                };
-
+        <Node
+            ref={props.forwardedRef}
+            onPress={props.onPress}
+            onLongPress={(e) => {
                 e.preventDefault();
                 HapticFeedback.trigger();
-                props.onSecondaryInteraction(mapEvent);
+                props.onSecondaryInteraction(e);
             }}
-        >
-            <Node
-                ref={props.forwardedRef}
-                onPress={props.onPress}
-                onPressIn={props.onPressIn}
-                onPressOut={props.onPressOut}
+            onPressIn={props.onPressIn}
+            onPressOut={props.onPressOut}
             // eslint-disable-next-line react/jsx-props-no-spreading
-                {...(_.omit(props, 'onLongPress'))}
-            >
-                {props.children}
-            </Node>
-        </LongPressGestureHandler>
-
+            {...(_.omit(props, 'onLongPress'))}
+        >
+            {props.children}
+        </Node>
     );
 };
 
diff --git a/src/components/PressableWithoutFocus.js b/src/components/PressableWithoutFocus.js
index 30668608496f..10ea16c71d06 100644
--- a/src/components/PressableWithoutFocus.js
+++ b/src/components/PressableWithoutFocus.js
@@ -12,6 +12,9 @@ const propTypes = {
     /** Callback for onPress event */
     onPress: PropTypes.func.isRequired,
 
+    /** Callback for onLongPress event */
+    onLongPress: PropTypes.func,
+
     /** Styles that should be passed to touchable container */
     // eslint-disable-next-line react/forbid-prop-types
     styles: PropTypes.arrayOf(PropTypes.object),
@@ -19,6 +22,7 @@ const propTypes = {
 
 const defaultProps = {
     styles: [],
+    onLongPress: undefined,
 };
 
 /**
@@ -41,7 +45,12 @@ class PressableWithoutFocus extends React.Component {
 
     render() {
         return (
-            <Pressable onPress={this.pressAndBlur} ref={el => this.pressableRef = el} style={this.props.styles}>
+            <Pressable
+                onPress={this.pressAndBlur}
+                onLongPress={this.props.onLongPress}
+                ref={el => this.pressableRef = el}
+                style={this.props.styles}
+            >
                 {this.props.children}
             </Pressable>
         );
diff --git a/src/components/ReportActionItem/IOUAction.js b/src/components/ReportActionItem/IOUAction.js
index 8896b4a41b58..ba78f8cd9cb8 100644
--- a/src/components/ReportActionItem/IOUAction.js
+++ b/src/components/ReportActionItem/IOUAction.js
@@ -25,6 +25,12 @@ const propTypes = {
     /** Is this IOUACTION the most recent? */
     isMostRecentIOUReportAction: PropTypes.bool.isRequired,
 
+    /** Popover context menu anchor, used for showing context menu */
+    contextMenuAnchor: PropTypes.shape({current: PropTypes.elementType}),
+
+    /** Callback for updating context menu active state, used for showing context menu */
+    checkIfContextMenuActive: PropTypes.func,
+
     /* Onyx Props */
     /** chatReport associated with iouReport */
     chatReport: PropTypes.shape({
@@ -48,6 +54,8 @@ const propTypes = {
 };
 
 const defaultProps = {
+    contextMenuAnchor: undefined,
+    checkIfContextMenuActive: () => {},
     chatReport: {
         participants: [],
     },
@@ -79,13 +87,19 @@ const IOUAction = (props) => {
         <>
             <IOUQuote
                 action={props.action}
+                chatReportID={props.chatReportID}
+                contextMenuAnchor={props.contextMenuAnchor}
                 shouldAllowViewDetails={Boolean(props.action.originalMessage.IOUReportID)}
                 onViewDetailsPressed={launchDetailsModal}
+                checkIfContextMenuActive={props.checkIfContextMenuActive}
             />
             {shouldShowIOUPreview && (
                 <IOUPreview
                     iouReportID={props.action.originalMessage.IOUReportID.toString()}
                     chatReportID={props.chatReportID}
+                    action={props.action}
+                    contextMenuAnchor={props.contextMenuAnchor}
+                    checkIfContextMenuActive={props.checkIfContextMenuActive}
                     shouldShowPendingConversionMessage={shouldShowPendingConversionMessage}
                     onPayButtonPressed={launchDetailsModal}
                     onPreviewPressed={launchDetailsModal}
diff --git a/src/components/ReportActionItem/IOUPreview.js b/src/components/ReportActionItem/IOUPreview.js
index 1c997119d6d7..3a149f683c21 100644
--- a/src/components/ReportActionItem/IOUPreview.js
+++ b/src/components/ReportActionItem/IOUPreview.js
@@ -22,6 +22,10 @@ import Text from '../Text';
 import * as PaymentMethods from '../../libs/actions/PaymentMethods';
 import OfflineWithFeedback from '../OfflineWithFeedback';
 import walletTermsPropTypes from '../../pages/EnablePayments/walletTermsPropTypes';
+import ControlSelection from '../../libs/ControlSelection';
+import * as DeviceCapabilities from '../../libs/DeviceCapabilities';
+import reportActionPropTypes from '../../pages/home/report/reportActionPropTypes';
+import {showContextMenuForReport} from '../ShowContextMenuContext';
 import * as ReportUtils from '../../libs/ReportUtils';
 import Button from '../Button';
 
@@ -42,6 +46,15 @@ const propTypes = {
     /** Callback for the preview pressed */
     onPreviewPressed: PropTypes.func,
 
+    /** All the data of the action, used for showing context menu */
+    action: PropTypes.shape(reportActionPropTypes),
+
+    /** Popover context menu anchor, used for showing context menu */
+    contextMenuAnchor: PropTypes.shape({current: PropTypes.elementType}),
+
+    /** Callback for updating context menu active state, used for showing context menu */
+    checkIfContextMenuActive: PropTypes.func,
+
     /** Extra styles to pass to View wrapper */
     // eslint-disable-next-line react/forbid-prop-types
     containerStyles: PropTypes.arrayOf(PropTypes.object),
@@ -96,6 +109,9 @@ const defaultProps = {
     shouldHidePayButton: false,
     onPayButtonPressed: null,
     onPreviewPressed: () => {},
+    action: undefined,
+    contextMenuAnchor: undefined,
+    checkIfContextMenuActive: () => {},
     containerStyles: [],
     walletTerms: {},
     pendingAction: null,
@@ -129,8 +145,30 @@ const IOUPreview = (props) => {
             {style: 'currency', currency: props.iouReport.currency},
         ) : '';
     const avatarTooltip = [Str.removeSMSDomain(managerEmail), Str.removeSMSDomain(ownerEmail)];
+
+    const showContextMenu = (event) => {
+        // Use action and shouldHidePayButton props to check if we are in IOUDetailsModal,
+        // if it's true, do nothing when user long press, otherwise show context menu.
+        if (!props.action && props.shouldHidePayButton) {
+            return;
+        }
+
+        showContextMenuForReport(
+            event,
+            props.contextMenuAnchor,
+            props.chatReportID,
+            props.action,
+            props.checkIfContextMenuActive,
+        );
+    };
+
     return (
-        <TouchableWithoutFeedback onPress={props.onPreviewPressed}>
+        <TouchableWithoutFeedback
+            onPress={props.onPreviewPressed}
+            onPressIn={() => DeviceCapabilities.canUseTouchScreen() && ControlSelection.block()}
+            onPressOut={() => ControlSelection.unblock()}
+            onLongPress={showContextMenu}
+        >
             <View style={[styles.iouPreviewBox, ...props.containerStyles]}>
                 <OfflineWithFeedback
                     pendingAction={props.pendingAction}
@@ -194,6 +232,9 @@ const IOUPreview = (props) => {
                                 <Button
                                     style={styles.mt4}
                                     onPress={props.onPayButtonPressed}
+                                    onPressIn={() => DeviceCapabilities.canUseTouchScreen() && ControlSelection.block()}
+                                    onPressOut={() => ControlSelection.unblock()}
+                                    onLongPress={showContextMenu}
                                     text={props.translate('iou.pay')}
                                     success
                                     medium
diff --git a/src/components/ReportActionItem/IOUQuote.js b/src/components/ReportActionItem/IOUQuote.js
index 11544cbc60dd..1a51e3242857 100644
--- a/src/components/ReportActionItem/IOUQuote.js
+++ b/src/components/ReportActionItem/IOUQuote.js
@@ -10,23 +10,37 @@ import styles from '../../styles/styles';
 import themeColors from '../../styles/themes/default';
 import reportActionPropTypes from '../../pages/home/report/reportActionPropTypes';
 import withLocalize, {withLocalizePropTypes} from '../withLocalize';
+import ControlSelection from '../../libs/ControlSelection';
+import * as DeviceCapabilities from '../../libs/DeviceCapabilities';
+import {showContextMenuForReport} from '../ShowContextMenuContext';
 
 const propTypes = {
     /** All the data of the action */
     action: PropTypes.shape(reportActionPropTypes).isRequired,
 
+    /** The associated chatReport */
+    chatReportID: PropTypes.string.isRequired,
+
+    /** Popover context menu anchor, used for showing context menu */
+    contextMenuAnchor: PropTypes.shape({current: PropTypes.elementType}),
+
     /** Whether it is allowed to view details. */
     shouldAllowViewDetails: PropTypes.bool,
 
     /** Callback invoked when View Details is pressed */
     onViewDetailsPressed: PropTypes.func,
 
+    /** Callback for updating context menu active state, used for showing context menu */
+    checkIfContextMenuActive: PropTypes.func,
+
     ...withLocalizePropTypes,
 };
 
 const defaultProps = {
+    contextMenuAnchor: null,
     shouldAllowViewDetails: false,
     onViewDetailsPressed: () => {},
+    checkIfContextMenuActive: () => {},
 };
 
 const IOUQuote = props => (
@@ -37,6 +51,15 @@ const IOUQuote = props => (
                 onPress={props.shouldAllowViewDetails
                     ? props.onViewDetailsPressed
                     : () => {}}
+                onPressIn={() => DeviceCapabilities.canUseTouchScreen() && ControlSelection.block()}
+                onPressOut={() => ControlSelection.unblock()}
+                onLongPress={event => showContextMenuForReport(
+                    event,
+                    props.contextMenuAnchor,
+                    props.chatReportID,
+                    props.action,
+                    props.checkIfContextMenuActive,
+                )}
                 style={[styles.flexRow, styles.justifyContentBetween,
                     props.shouldAllowViewDetails
                         ? undefined
diff --git a/src/components/ShowContextMenuContext.js b/src/components/ShowContextMenuContext.js
new file mode 100644
index 000000000000..d063d8ff1eb7
--- /dev/null
+++ b/src/components/ShowContextMenuContext.js
@@ -0,0 +1,40 @@
+import React from 'react';
+import * as ReportActionContextMenu from '../pages/home/report/ContextMenu/ReportActionContextMenu';
+import * as ContextMenuActions from '../pages/home/report/ContextMenu/ContextMenuActions';
+
+const ShowContextMenuContext = React.createContext({
+    anchor: null,
+    reportID: null,
+    action: undefined,
+    checkIfContextMenuActive: () => {},
+});
+
+ShowContextMenuContext.displayName = 'ShowContextMenuContext';
+
+/**
+ * Show the report action context menu.
+ *
+ * @param {Object} event - Press event object
+ * @param {Element} anchor - Context menu anchor
+ * @param {String} reportID - Active Report ID
+ * @param {Object} action - ReportAction for ContextMenu
+ * @param {Function} checkIfContextMenuActive Callback to update context menu active state
+ */
+function showContextMenuForReport(event, anchor, reportID, action, checkIfContextMenuActive) {
+    ReportActionContextMenu.showContextMenu(
+        ContextMenuActions.CONTEXT_MENU_TYPES.REPORT_ACTION,
+        event,
+        '',
+        anchor,
+        reportID,
+        action,
+        '',
+        checkIfContextMenuActive,
+        checkIfContextMenuActive,
+    );
+}
+
+export {
+    ShowContextMenuContext,
+    showContextMenuForReport,
+};
diff --git a/src/pages/home/report/ReportActionItem.js b/src/pages/home/report/ReportActionItem.js
index be4eb73886ca..80323f34135a 100644
--- a/src/pages/home/report/ReportActionItem.js
+++ b/src/pages/home/report/ReportActionItem.js
@@ -33,6 +33,7 @@ import * as ReportUtils from '../../../libs/ReportUtils';
 import OfflineWithFeedback from '../../../components/OfflineWithFeedback';
 import * as ReportActions from '../../../libs/actions/ReportActions';
 import reportPropTypes from '../../reportPropTypes';
+import {ShowContextMenuContext} from '../../../components/ShowContextMenuContext';
 import focusTextInputAfterAnimation from '../../../libs/focusTextInputAfterAnimation';
 
 const propTypes = {
@@ -150,26 +151,39 @@ class ReportActionItem extends Component {
                     action={this.props.action}
                     isMostRecentIOUReportAction={this.props.isMostRecentIOUReportAction}
                     isHovered={hovered}
+                    contextMenuAnchor={this.popoverAnchor}
+                    checkIfContextMenuActive={this.checkIfContextMenuActive}
                 />
             );
         } else {
-            children = !this.props.draftMessage
-                ? (
-                    <ReportActionItemMessage action={this.props.action} />
-                ) : (
-                    <ReportActionItemMessageEdit
-                        action={this.props.action}
-                        draftMessage={this.props.draftMessage}
-                        reportID={this.props.report.reportID}
-                        index={this.props.index}
-                        ref={el => this.textInput = el}
-                        report={this.props.report}
-                        shouldDisableEmojiPicker={
-                            (ReportUtils.chatIncludesConcierge(this.props.report) && User.isBlockedFromConcierge(this.props.blockedFromConcierge))
-                            || ReportUtils.isArchivedRoom(this.props.report)
-                        }
-                    />
-                );
+            children = (
+                <ShowContextMenuContext.Provider
+                    value={{
+                        anchor: this.popoverAnchor,
+                        reportID: this.props.report.reportID,
+                        action: this.props.action,
+                        checkIfContextMenuActive: this.checkIfContextMenuActive,
+                    }}
+                >
+                    {!this.props.draftMessage
+                        ? (
+                            <ReportActionItemMessage action={this.props.action} />
+                        ) : (
+                            <ReportActionItemMessageEdit
+                                action={this.props.action}
+                                draftMessage={this.props.draftMessage}
+                                reportID={this.props.report.reportID}
+                                index={this.props.index}
+                                ref={el => this.textInput = el}
+                                report={this.props.report}
+                                shouldDisableEmojiPicker={
+                                    (ReportUtils.chatIncludesConcierge(this.props.report) && User.isBlockedFromConcierge(this.props.blockedFromConcierge))
+                                    || ReportUtils.isArchivedRoom(this.props.report)
+                                }
+                            />
+                        )}
+                </ShowContextMenuContext.Provider>
+            );
         }
         return children;
     }