diff --git a/src/components/AttachmentPicker/attachmentPickerPropTypes.js b/src/components/AttachmentPicker/attachmentPickerPropTypes.js
index 3b6fb7d041c5..1161819408ff 100644
--- a/src/components/AttachmentPicker/attachmentPickerPropTypes.js
+++ b/src/components/AttachmentPicker/attachmentPickerPropTypes.js
@@ -24,10 +24,14 @@ const propTypes = {
 
     /** The types of files that can be selected with this picker. */
     type: PropTypes.oneOf([CONST.ATTACHMENT_PICKER_TYPE.FILE, CONST.ATTACHMENT_PICKER_TYPE.IMAGE]),
+
+    /** Optional callback to fire when we want to do something once the modal is hidden. */
+    onModalHide: PropTypes.func,
 };
 
 const defaultProps = {
     type: CONST.ATTACHMENT_PICKER_TYPE.FILE,
+    onModalHide: () => {},
 };
 
 export {propTypes, defaultProps};
diff --git a/src/components/AttachmentPicker/index.js b/src/components/AttachmentPicker/index.js
index fb2e95b88317..feb9bf714bb2 100644
--- a/src/components/AttachmentPicker/index.js
+++ b/src/components/AttachmentPicker/index.js
@@ -28,6 +28,7 @@ function getAcceptableFileTypes(type) {
 function AttachmentPicker(props) {
     const fileInput = useRef();
     const onPicked = useRef();
+    const onModalHide = useRef();
     return (
         <>
             <input
@@ -51,12 +52,21 @@ function AttachmentPicker(props) {
                 }}
                 // We are stopping the event propagation because triggering the `click()` on the hidden input
                 // causes the event to unexpectedly bubble up to anything wrapping this component e.g. Pressable
-                onClick={(e) => e.stopPropagation()}
+                onClick={(e) => {
+                    e.stopPropagation();
+
+                    // We add this focus event listener to call the onModalHide callback when user does not select any files
+                    // i.e. clicks cancel in the native file picker modal - this is when the app gets the focus back
+                    window.addEventListener('focus', onModalHide.current, {
+                        once: true, // this removes the listener after running once
+                    });
+                }}
                 accept={getAcceptableFileTypes(props.type)}
             />
             {props.children({
-                openPicker: ({onPicked: newOnPicked}) => {
+                openPicker: ({onPicked: newOnPicked, onModalHide: newOnModalHide}) => {
                     onPicked.current = newOnPicked;
+                    onModalHide.current = newOnModalHide;
                     fileInput.current.click();
                 },
             })}
diff --git a/src/components/AttachmentPicker/index.native.js b/src/components/AttachmentPicker/index.native.js
index b0b1222316f0..3e2cc268c527 100644
--- a/src/components/AttachmentPicker/index.native.js
+++ b/src/components/AttachmentPicker/index.native.js
@@ -100,6 +100,7 @@ class AttachmentPicker extends Component {
 
         this.state = {
             isVisible: false,
+            onModalHide: () => {},
             focusedIndex: -1,
         };
 
@@ -232,6 +233,8 @@ class AttachmentPicker extends Component {
         return new Promise((resolve, reject) => {
             imagePickerFunc(getImagePickerOptions(this.props.type), (response) => {
                 if (response.didCancel) {
+                    this.state.onModalHide();
+
                     // When the user cancelled resolve with no attachment
                     return resolve();
                 }
@@ -276,6 +279,7 @@ class AttachmentPicker extends Component {
     showDocumentPicker() {
         return RNDocumentPicker.pick(documentPickerOptions).catch((error) => {
             if (RNDocumentPicker.isCancel(error)) {
+                this.state.onModalHide();
                 return;
             }
 
@@ -341,7 +345,12 @@ class AttachmentPicker extends Component {
      */
     renderChildren() {
         return this.props.children({
-            openPicker: ({onPicked}) => this.open(onPicked),
+            openPicker: ({onPicked, onModalHide}) => {
+                this.open(onPicked);
+                if (onModalHide) {
+                    this.setState({onModalHide});
+                }
+            },
         });
     }
 
@@ -352,7 +361,15 @@ class AttachmentPicker extends Component {
                     onClose={this.close}
                     isVisible={this.state.isVisible}
                     anchorPosition={styles.createMenuPosition}
-                    onModalHide={this.onModalHide}
+                    onModalHide={() => {
+                        // this.modalHide is triggered when the modal is closed by selecting an item and
+                        // this.state.onModalHide is triggered when the modal is closed by touching outside or back button
+                        if (this.onModalHide) {
+                            this.onModalHide();
+                        } else {
+                            this.state.onModalHide();
+                        }
+                    }}
                 >
                     <View style={this.props.isSmallScreenWidth ? {} : styles.createMenuContainer}>
                         <ArrowKeyFocusManager
diff --git a/src/components/Modal/index.ios.js b/src/components/Modal/index.ios.js
index d8206d12532d..54c2ee6322e2 100644
--- a/src/components/Modal/index.ios.js
+++ b/src/components/Modal/index.ios.js
@@ -1,13 +1,36 @@
-import React from 'react';
+import React, {useState, useEffect} from 'react';
+import {Keyboard} from 'react-native';
+import compose from '../../libs/compose';
+import withKeyboardState from '../withKeyboardState';
 import withWindowDimensions from '../withWindowDimensions';
 import BaseModal from './BaseModal';
 import {propTypes, defaultProps} from './modalPropTypes';
 
 function Modal(props) {
+    const [isVisible, setIsVisible] = useState(false);
+
+    // This closes the keyboard before opening the modal to avoid the issue where iOS automatically reopens
+    // the keyboard if it was already open before any modals were opened. We manage the keyboard behaviour
+    // explicitly at other places in the app to be consistent across all platforms
+    useEffect(() => {
+        if (!props.isVisible) {
+            setIsVisible(false);
+        } else if (props.isKeyboardShown) {
+            const keyboardListener = Keyboard.addListener('keyboardDidHide', () => {
+                setIsVisible(true);
+                keyboardListener.remove();
+            });
+            Keyboard.dismiss();
+        } else {
+            setIsVisible(true);
+        }
+    }, [props.isVisible, props.isKeyboardShown]);
+
     return (
         <BaseModal
             // eslint-disable-next-line react/jsx-props-no-spreading
             {...props}
+            isVisible={isVisible}
         >
             {props.children}
         </BaseModal>
@@ -17,4 +40,4 @@ function Modal(props) {
 Modal.propTypes = propTypes;
 Modal.defaultProps = defaultProps;
 Modal.displayName = 'Modal';
-export default withWindowDimensions(Modal);
+export default compose(withWindowDimensions, withKeyboardState)(Modal);
diff --git a/src/components/PopoverMenu/index.js b/src/components/PopoverMenu/index.js
index 1cafa9e12664..33ad89cd198e 100644
--- a/src/components/PopoverMenu/index.js
+++ b/src/components/PopoverMenu/index.js
@@ -61,19 +61,24 @@ function PopoverMenu(props) {
         {isActive: props.isVisible},
     );
 
+    const resetFocusAndHideModal = () => {
+        setFocusedIndex(-1); // Reset the focusedIndex on modal hide
+        if (selectedItemIndex !== null) {
+            props.menuItems[selectedItemIndex].onSelected();
+            setSelectedItemIndex(null);
+        } else if (props.onModalHide) {
+            // trigger the onModalHide callback only when modal is closed by clicking outside or back button
+            props.onModalHide();
+        }
+    };
+
     return (
         <PopoverWithMeasuredContent
             anchorPosition={props.anchorPosition}
             anchorAlignment={props.anchorAlignment}
             onClose={props.onClose}
             isVisible={props.isVisible}
-            onModalHide={() => {
-                setFocusedIndex(-1);
-                if (selectedItemIndex !== null) {
-                    props.menuItems[selectedItemIndex].onSelected();
-                    setSelectedItemIndex(null);
-                }
-            }}
+            onModalHide={resetFocusAndHideModal}
             animationIn={props.animationIn}
             animationOut={props.animationOut}
             animationInTiming={props.animationInTiming}
diff --git a/src/pages/home/report/ReportActionCompose.js b/src/pages/home/report/ReportActionCompose.js
index e5a5bf61716f..3680106e7a79 100644
--- a/src/pages/home/report/ReportActionCompose.js
+++ b/src/pages/home/report/ReportActionCompose.js
@@ -177,6 +177,7 @@ class ReportActionCompose extends React.Component {
         this.getMoneyRequestOptions = this.getMoneyRequestOptions.bind(this);
         this.getTaskOption = this.getTaskOption.bind(this);
         this.addAttachment = this.addAttachment.bind(this);
+        this.finishAddAttachmentFlow = this.finishAddAttachmentFlow.bind(this);
         this.insertSelectedEmoji = this.insertSelectedEmoji.bind(this);
         this.insertSelectedMention = this.insertSelectedMention.bind(this);
         this.setExceededMaxCommentLength = this.setExceededMaxCommentLength.bind(this);
@@ -206,6 +207,7 @@ class ReportActionCompose extends React.Component {
         const isMobileSafari = Browser.isMobileSafari();
 
         this.state = {
+            isInAddAttachmentFlow: false,
             isFocused: this.shouldFocusInputOnScreenFocus && !this.props.modal.isVisible && !this.props.modal.willAlertModalBecomeVisible && this.props.shouldShowComposeInput,
             isFullComposerAvailable: props.isComposerFullSize,
             textInputShouldClear: false,
@@ -257,7 +259,13 @@ class ReportActionCompose extends React.Component {
         // We want to focus or refocus the input when a modal has been closed or the underlying screen is refocused.
         // We avoid doing this on native platforms since the software keyboard popping
         // open creates a jarring and broken UX.
-        if (this.willBlurTextInputOnTapOutside && !this.props.modal.isVisible && this.props.isFocused && (prevProps.modal.isVisible || !prevProps.isFocused)) {
+        if (
+            this.willBlurTextInputOnTapOutside &&
+            !this.props.modal.isVisible &&
+            this.props.isFocused &&
+            !this.state.isInAddAttachmentFlow &&
+            (prevProps.modal.isVisible || !prevProps.isFocused)
+        ) {
             this.focus();
         }
 
@@ -412,6 +420,15 @@ class ReportActionCompose extends React.Component {
         }
     }
 
+    /**
+     * Set isInAddAttachmentFlow state
+     *
+     * @param {Boolean} value
+     */
+    setIsInAddAttachmentFlow(value) {
+        this.setState({isInAddAttachmentFlow: value});
+    }
+
     /**
      * Determines if we can show the task option
      * @param {Array} reportParticipants
@@ -878,6 +895,17 @@ class ReportActionCompose extends React.Component {
         this.setTextInputShouldClear(false);
     }
 
+    /**
+     * Set the focus back to the composer
+     */
+    finishAddAttachmentFlow() {
+        this.setIsInAddAttachmentFlow(false);
+
+        // Explicitly focus the composer from here as componentDidUpdate does not do that in native
+        // because willBlurTextInputOnTapOutside is false on native which doesn't let it focus
+        this.focus(true);
+    }
+
     /**
      * Add a new comment to this chat
      *
@@ -953,6 +981,7 @@ class ReportActionCompose extends React.Component {
                             onConfirm={this.addAttachment}
                             onModalShow={() => this.setState({isAttachmentPreviewActive: true})}
                             onModalHide={() => {
+                                this.finishAddAttachmentFlow();
                                 this.shouldBlockEmojiCalc = false;
                                 this.shouldBlockMentionCalc = false;
                                 this.setState({isAttachmentPreviewActive: false});
@@ -1016,6 +1045,10 @@ class ReportActionCompose extends React.Component {
 
                                                                 // Drop focus to avoid blue focus ring.
                                                                 this.actionButton.blur();
+
+                                                                // we blur the input here to avoid an android specific issue where the keyboard
+                                                                // doesn't open when we re-focus the input due to it never losing focus
+                                                                this.textInput.blur();
                                                                 this.setMenuVisibility(true);
                                                             }}
                                                             style={styles.composerSizeButton}
@@ -1031,7 +1064,11 @@ class ReportActionCompose extends React.Component {
                                                     animationInTiming={CONST.ANIMATION_IN_TIMING}
                                                     isVisible={this.state.isMenuVisible}
                                                     onClose={() => this.setMenuVisibility(false)}
-                                                    onItemSelected={() => this.setMenuVisibility(false)}
+                                                    onModalHide={this.finishAddAttachmentFlow}
+                                                    onItemSelected={(item) => {
+                                                        this.setMenuVisibility(false);
+                                                        this.setIsInAddAttachmentFlow(item.text === this.props.translate('reportActionCompose.addAttachment'));
+                                                    }}
                                                     anchorPosition={styles.createMenuPositionReportActionCompose(this.props.windowHeight)}
                                                     anchorAlignment={{horizontal: CONST.MODAL.ANCHOR_ORIGIN_HORIZONTAL.LEFT, vertical: CONST.MODAL.ANCHOR_ORIGIN_VERTICAL.BOTTOM}}
                                                     menuItems={[
@@ -1050,6 +1087,7 @@ class ReportActionCompose extends React.Component {
 
                                                                 openPicker({
                                                                     onPicked: displayFileInModal,
+                                                                    onModalHide: this.finishAddAttachmentFlow,
                                                                 });
                                                             },
                                                         },