diff --git a/patches/react-native-web+0.19.9+005+image-header-support.patch b/patches/react-native-web+0.19.9+005+image-header-support.patch
new file mode 100644
index 000000000000..4652e22662f0
--- /dev/null
+++ b/patches/react-native-web+0.19.9+005+image-header-support.patch
@@ -0,0 +1,200 @@
+diff --git a/node_modules/react-native-web/dist/exports/Image/index.js b/node_modules/react-native-web/dist/exports/Image/index.js
+index 95355d5..19109fc 100644
+--- a/node_modules/react-native-web/dist/exports/Image/index.js
++++ b/node_modules/react-native-web/dist/exports/Image/index.js
+@@ -135,7 +135,22 @@ function resolveAssetUri(source) {
+   }
+   return uri;
+ }
+-var Image = /*#__PURE__*/React.forwardRef((props, ref) => {
++function raiseOnErrorEvent(uri, _ref) {
++  var onError = _ref.onError,
++    onLoadEnd = _ref.onLoadEnd;
++  if (onError) {
++    onError({
++      nativeEvent: {
++        error: "Failed to load resource " + uri + " (404)"
++      }
++    });
++  }
++  if (onLoadEnd) onLoadEnd();
++}
++function hasSourceDiff(a, b) {
++  return a.uri !== b.uri || JSON.stringify(a.headers) !== JSON.stringify(b.headers);
++}
++var BaseImage = /*#__PURE__*/React.forwardRef((props, ref) => {
+   var ariaLabel = props['aria-label'],
+     blurRadius = props.blurRadius,
+     defaultSource = props.defaultSource,
+@@ -236,16 +251,10 @@ var Image = /*#__PURE__*/React.forwardRef((props, ref) => {
+         }
+       }, function error() {
+         updateState(ERRORED);
+-        if (onError) {
+-          onError({
+-            nativeEvent: {
+-              error: "Failed to load resource " + uri + " (404)"
+-            }
+-          });
+-        }
+-        if (onLoadEnd) {
+-          onLoadEnd();
+-        }
++        raiseOnErrorEvent(uri, {
++          onError,
++          onLoadEnd
++        });
+       });
+     }
+     function abortPendingRequest() {
+@@ -277,10 +286,78 @@ var Image = /*#__PURE__*/React.forwardRef((props, ref) => {
+     suppressHydrationWarning: true
+   }), hiddenImage, createTintColorSVG(tintColor, filterRef.current));
+ });
+-Image.displayName = 'Image';
++BaseImage.displayName = 'Image';
++
++/**
++ * This component handles specifically loading an image source with headers
++ * default source is never loaded using headers
++ */
++var ImageWithHeaders = /*#__PURE__*/React.forwardRef((props, ref) => {
++  // $FlowIgnore: This component would only be rendered when `source` matches `ImageSource`
++  var nextSource = props.source;
++  var _React$useState3 = React.useState(''),
++    blobUri = _React$useState3[0],
++    setBlobUri = _React$useState3[1];
++  var request = React.useRef({
++    cancel: () => {},
++    source: {
++      uri: '',
++      headers: {}
++    },
++    promise: Promise.resolve('')
++  });
++  var onError = props.onError,
++    onLoadStart = props.onLoadStart,
++    onLoadEnd = props.onLoadEnd;
++  React.useEffect(() => {
++    if (!hasSourceDiff(nextSource, request.current.source)) {
++      return;
++    }
++
++    // When source changes we want to clean up any old/running requests
++    request.current.cancel();
++    if (onLoadStart) {
++      onLoadStart();
++    }
++
++    // Store a ref for the current load request so we know what's the last loaded source,
++    // and so we can cancel it if a different source is passed through props
++    request.current = ImageLoader.loadWithHeaders(nextSource);
++    request.current.promise.then(uri => setBlobUri(uri)).catch(() => raiseOnErrorEvent(request.current.source.uri, {
++      onError,
++      onLoadEnd
++    }));
++  }, [nextSource, onLoadStart, onError, onLoadEnd]);
++
++  // Cancel any request on unmount
++  React.useEffect(() => request.current.cancel, []);
++  var propsToPass = _objectSpread(_objectSpread({}, props), {}, {
++    // `onLoadStart` is called from the current component
++    // We skip passing it down to prevent BaseImage raising it a 2nd time
++    onLoadStart: undefined,
++    // Until the current component resolves the request (using headers)
++    // we skip forwarding the source so the base component doesn't attempt
++    // to load the original source
++    source: blobUri ? _objectSpread(_objectSpread({}, nextSource), {}, {
++      uri: blobUri
++    }) : undefined
++  });
++  return /*#__PURE__*/React.createElement(BaseImage, _extends({
++    ref: ref
++  }, propsToPass));
++});
+ 
+ // $FlowIgnore: This is the correct type, but casting makes it unhappy since the variables aren't defined yet
+-var ImageWithStatics = Image;
++var ImageWithStatics = /*#__PURE__*/React.forwardRef((props, ref) => {
++  if (props.source && props.source.headers) {
++    return /*#__PURE__*/React.createElement(ImageWithHeaders, _extends({
++      ref: ref
++    }, props));
++  }
++  return /*#__PURE__*/React.createElement(BaseImage, _extends({
++    ref: ref
++  }, props));
++});
+ ImageWithStatics.getSize = function (uri, success, failure) {
+   ImageLoader.getSize(uri, success, failure);
+ };
+diff --git a/node_modules/react-native-web/dist/modules/ImageLoader/index.js b/node_modules/react-native-web/dist/modules/ImageLoader/index.js
+index bc06a87..e309394 100644
+--- a/node_modules/react-native-web/dist/modules/ImageLoader/index.js
++++ b/node_modules/react-native-web/dist/modules/ImageLoader/index.js
+@@ -76,7 +76,7 @@ var ImageLoader = {
+       var image = requests["" + requestId];
+       if (image) {
+         var naturalHeight = image.naturalHeight,
+-          naturalWidth = image.naturalWidth;
++            naturalWidth = image.naturalWidth;
+         if (naturalHeight && naturalWidth) {
+           success(naturalWidth, naturalHeight);
+           complete = true;
+@@ -102,11 +102,19 @@ var ImageLoader = {
+     id += 1;
+     var image = new window.Image();
+     image.onerror = onError;
+-    image.onload = e => {
++    image.onload = nativeEvent => {
+       // avoid blocking the main thread
+-      var onDecode = () => onLoad({
+-        nativeEvent: e
+-      });
++      var onDecode = () => {
++        // Append `source` to match RN's ImageLoadEvent interface
++        nativeEvent.source = {
++          uri: image.src,
++          width: image.naturalWidth,
++          height: image.naturalHeight
++        };
++        onLoad({
++          nativeEvent
++        });
++      };
+       if (typeof image.decode === 'function') {
+         // Safari currently throws exceptions when decoding svgs.
+         // We want to catch that error and allow the load handler
+@@ -120,6 +128,32 @@ var ImageLoader = {
+     requests["" + id] = image;
+     return id;
+   },
++  loadWithHeaders(source) {
++    var uri;
++    var abortController = new AbortController();
++    var request = new Request(source.uri, {
++      headers: source.headers,
++      signal: abortController.signal
++    });
++    request.headers.append('accept', 'image/*');
++    var promise = fetch(request).then(response => response.blob()).then(blob => {
++      uri = URL.createObjectURL(blob);
++      return uri;
++    }).catch(error => {
++      if (error.name === 'AbortError') {
++        return '';
++      }
++      throw error;
++    });
++    return {
++      promise,
++      source,
++      cancel: () => {
++        abortController.abort();
++        URL.revokeObjectURL(uri);
++      }
++    };
++  },
+   prefetch(uri) {
+     return new Promise((resolve, reject) => {
+       ImageLoader.load(uri, () => {
diff --git a/src/components/Image/BaseImage.js b/src/components/Image/BaseImage.js
new file mode 100644
index 000000000000..cd2326900c6c
--- /dev/null
+++ b/src/components/Image/BaseImage.js
@@ -0,0 +1,29 @@
+import React, {useCallback} from 'react';
+import {Image as RNImage} from 'react-native';
+import {defaultProps, imagePropTypes} from './imagePropTypes';
+
+function BaseImage({onLoad, ...props}) {
+    const imageLoadedSuccessfully = useCallback(
+        ({nativeEvent}) => {
+            // We override `onLoad`, so both web and native have the same signature
+            const {width, height} = nativeEvent.source;
+            onLoad({nativeEvent: {width, height}});
+        },
+        [onLoad],
+    );
+
+    return (
+        <RNImage
+            // Only subscribe to onLoad when a handler is provided to avoid unnecessary event registrations, optimizing performance.
+            onLoad={onLoad ? imageLoadedSuccessfully : undefined}
+            // eslint-disable-next-line react/jsx-props-no-spreading
+            {...props}
+        />
+    );
+}
+
+BaseImage.propTypes = imagePropTypes;
+BaseImage.defaultProps = defaultProps;
+BaseImage.displayName = 'BaseImage';
+
+export default BaseImage;
diff --git a/src/components/Image/BaseImage.native.js b/src/components/Image/BaseImage.native.js
new file mode 100644
index 000000000000..a621947267a1
--- /dev/null
+++ b/src/components/Image/BaseImage.native.js
@@ -0,0 +1,3 @@
+import RNFastImage from 'react-native-fast-image';
+
+export default RNFastImage;
diff --git a/src/components/Image/index.js b/src/components/Image/index.js
index ef1a69e19c12..8cee1cf95e14 100644
--- a/src/components/Image/index.js
+++ b/src/components/Image/index.js
@@ -1,51 +1,35 @@
 import lodashGet from 'lodash/get';
-import React, {useEffect, useMemo} from 'react';
-import {Image as RNImage} from 'react-native';
+import React, {useMemo} from 'react';
 import {withOnyx} from 'react-native-onyx';
-import _ from 'underscore';
+import CONST from '@src/CONST';
 import ONYXKEYS from '@src/ONYXKEYS';
+import BaseImage from './BaseImage';
 import {defaultProps, imagePropTypes} from './imagePropTypes';
 import RESIZE_MODES from './resizeModes';
 
-function Image(props) {
-    const {source: propsSource, isAuthTokenRequired, onLoad, session} = props;
-    /**
-     * Check if the image source is a URL - if so the `encryptedAuthToken` is appended
-     * to the source.
-     */
+function Image({source: propsSource, isAuthTokenRequired, session, ...forwardedProps}) {
+    // Update the source to include the auth token if required
     const source = useMemo(() => {
-        if (isAuthTokenRequired) {
-            // There is currently a `react-native-web` bug preventing the authToken being passed
-            // in the headers of the image request so the authToken is added as a query param.
-            // On native the authToken IS passed in the image request headers
-            const authToken = lodashGet(session, 'encryptedAuthToken', null);
-            return {uri: `${propsSource.uri}?encryptedAuthToken=${encodeURIComponent(authToken)}`};
+        if (typeof lodashGet(propsSource, 'uri') === 'number') {
+            return propsSource.uri;
         }
+        if (typeof propsSource !== 'number' && isAuthTokenRequired) {
+            const authToken = lodashGet(session, 'encryptedAuthToken');
+            return {
+                ...propsSource,
+                headers: {
+                    [CONST.CHAT_ATTACHMENT_TOKEN_KEY]: authToken,
+                },
+            };
+        }
+
         return propsSource;
         // The session prop is not required, as it causes the image to reload whenever the session changes. For more information, please refer to issue #26034.
         // eslint-disable-next-line react-hooks/exhaustive-deps
     }, [propsSource, isAuthTokenRequired]);
 
-    /**
-     * The natural image dimensions are retrieved using the updated source
-     * and as a result the `onLoad` event needs to be manually invoked to return these dimensions
-     */
-    useEffect(() => {
-        // If an onLoad callback was specified then manually call it and pass
-        // the natural image dimensions to match the native API
-        if (onLoad == null) {
-            return;
-        }
-        RNImage.getSize(source.uri, (width, height) => {
-            onLoad({nativeEvent: {width, height}});
-        });
-    }, [onLoad, source]);
-
-    // Omit the props which the underlying RNImage won't use
-    const forwardedProps = _.omit(props, ['source', 'onLoad', 'session', 'isAuthTokenRequired']);
-
     return (
-        <RNImage
+        <BaseImage
             // eslint-disable-next-line react/jsx-props-no-spreading
             {...forwardedProps}
             source={source}
diff --git a/src/components/Image/index.native.js b/src/components/Image/index.native.js
deleted file mode 100644
index cf5320392d1b..000000000000
--- a/src/components/Image/index.native.js
+++ /dev/null
@@ -1,63 +0,0 @@
-import lodashGet from 'lodash/get';
-import React from 'react';
-import RNFastImage from 'react-native-fast-image';
-import {withOnyx} from 'react-native-onyx';
-import CONST from '@src/CONST';
-import ONYXKEYS from '@src/ONYXKEYS';
-import {defaultProps, imagePropTypes} from './imagePropTypes';
-import RESIZE_MODES from './resizeModes';
-
-const dimensionsCache = new Map();
-
-function resolveDimensions(key) {
-    return dimensionsCache.get(key);
-}
-
-function Image(props) {
-    // eslint-disable-next-line react/destructuring-assignment
-    const {source, isAuthTokenRequired, session, ...rest} = props;
-
-    let imageSource = source;
-    if (source && source.uri && typeof source.uri === 'number') {
-        imageSource = source.uri;
-    }
-    if (typeof imageSource !== 'number' && isAuthTokenRequired) {
-        const authToken = lodashGet(props, 'session.encryptedAuthToken', null);
-        imageSource = {
-            ...source,
-            headers: authToken
-                ? {
-                      [CONST.CHAT_ATTACHMENT_TOKEN_KEY]: authToken,
-                  }
-                : null,
-        };
-    }
-
-    return (
-        <RNFastImage
-            // eslint-disable-next-line react/jsx-props-no-spreading
-            {...rest}
-            source={imageSource}
-            onLoad={(evt) => {
-                const {width, height} = evt.nativeEvent;
-                dimensionsCache.set(source.uri, {width, height});
-                if (props.onLoad) {
-                    props.onLoad(evt);
-                }
-            }}
-        />
-    );
-}
-
-Image.propTypes = imagePropTypes;
-Image.defaultProps = defaultProps;
-Image.displayName = 'Image';
-const ImageWithOnyx = withOnyx({
-    session: {
-        key: ONYXKEYS.SESSION,
-    },
-})(Image);
-ImageWithOnyx.resizeMode = RESIZE_MODES;
-ImageWithOnyx.resolveDimensions = resolveDimensions;
-
-export default ImageWithOnyx;
diff --git a/src/components/RoomHeaderAvatars.js b/src/components/RoomHeaderAvatars.js
index bd7a24d15f1f..4a1d60a869ad 100644
--- a/src/components/RoomHeaderAvatars.js
+++ b/src/components/RoomHeaderAvatars.js
@@ -33,7 +33,6 @@ function RoomHeaderAvatars(props) {
             <AttachmentModal
                 headerTitle={props.icons[0].name}
                 source={UserUtils.getFullSizeAvatar(props.icons[0].source, props.icons[0].id)}
-                isAuthTokenRequired
                 isWorkspaceAvatar={props.icons[0].type === CONST.ICON_TYPE_WORKSPACE}
                 originalFileName={props.icons[0].name}
             >
@@ -78,7 +77,6 @@ function RoomHeaderAvatars(props) {
                         <AttachmentModal
                             headerTitle={icon.name}
                             source={UserUtils.getFullSizeAvatar(icon.source, icon.id)}
-                            isAuthTokenRequired
                             originalFileName={icon.name}
                             isWorkspaceAvatar={icon.type === CONST.ICON_TYPE_WORKSPACE}
                         >
diff --git a/src/pages/DetailsPage.js b/src/pages/DetailsPage.js
index 66345107dbb1..6d3f0198bbfe 100755
--- a/src/pages/DetailsPage.js
+++ b/src/pages/DetailsPage.js
@@ -134,7 +134,6 @@ function DetailsPage(props) {
                                 <AttachmentModal
                                     headerTitle={details.displayName}
                                     source={UserUtils.getFullSizeAvatar(details.avatar, details.accountID)}
-                                    isAuthTokenRequired
                                     originalFileName={details.originalFileName}
                                 >
                                     {({show}) => (
diff --git a/src/pages/ProfilePage.js b/src/pages/ProfilePage.js
index 97ec3f99da3c..ece75b7f6918 100755
--- a/src/pages/ProfilePage.js
+++ b/src/pages/ProfilePage.js
@@ -159,7 +159,6 @@ function ProfilePage(props) {
                             <AttachmentModal
                                 headerTitle={displayName}
                                 source={UserUtils.getFullSizeAvatar(avatar, accountID)}
-                                isAuthTokenRequired
                                 originalFileName={originalFileName}
                                 fallbackSource={fallbackIcon}
                             >