diff --git a/config/proxyConfig.js b/config/proxyConfig.js
new file mode 100644
index 00000000000..0af64857d7b
--- /dev/null
+++ b/config/proxyConfig.js
@@ -0,0 +1,9 @@
+/**
+ * These are the base API root used to send requests to the proxy.
+ * We only specify for staging URLs as API requests are sent to the production
+ * servers by default.
+ */
+module.exports = {
+    STAGING: '/staging-',
+    STAGING_SECURE: '/staging-secure-',
+};
diff --git a/config/webpack/webpack.dev.js b/config/webpack/webpack.dev.js
index 0b48c4e5f35..926dcd0bcc1 100644
--- a/config/webpack/webpack.dev.js
+++ b/config/webpack/webpack.dev.js
@@ -21,6 +21,8 @@ module.exports = (env = {}) => portfinder.getPortPromise({port: BASE_PORT})
             : {
                 proxy: {
                     '/api': 'http://[::1]:9000',
+                    '/staging-api': 'http://[::1]:9000',
+                    '/staging-secure-api': 'http://[::1]:9000',
                     '/chat-attachments': 'http://[::1]:9000',
                 },
             };
diff --git a/src/CONFIG.js b/src/CONFIG.js
index 2dd63730b84..f6db312b7a1 100644
--- a/src/CONFIG.js
+++ b/src/CONFIG.js
@@ -78,4 +78,5 @@ export default {
     DEV_PORT: process.env.PORT || 8080,
     E2E_TESTING: lodashGet(Config, 'E2E_TESTING', 'false') === 'true',
     SEND_CRASH_REPORTS: lodashGet(Config, 'SEND_CRASH_REPORTS', 'false') === 'true',
+    IS_USING_WEB_PROXY: getPlatform() === 'web' && useWebProxy,
 };
diff --git a/src/libs/HttpUtils.js b/src/libs/HttpUtils.js
index a1cd16bcc4f..7d92bf4f491 100644
--- a/src/libs/HttpUtils.js
+++ b/src/libs/HttpUtils.js
@@ -5,15 +5,15 @@ import CONFIG from '../CONFIG';
 import CONST from '../CONST';
 import ONYXKEYS from '../ONYXKEYS';
 import HttpsError from './Errors/HttpsError';
-import shouldUseStagingServer from './shouldUseStagingServer';
 import getPlatform from './getPlatform';
+import proxyConfig from '../../config/proxyConfig';
 
 // Desktop and web use staging config too so we we should default to staging API endpoint if on those platforms
 const shouldDefaultToStaging = _.contains([CONST.PLATFORM.WEB, CONST.PLATFORM.DESKTOP], getPlatform());
-let stagingServerToggleState = false;
+let shouldUseStagingServer = false;
 Onyx.connect({
     key: ONYXKEYS.USER,
-    callback: val => stagingServerToggleState = lodashGet(val, 'shouldUseStagingServer', shouldDefaultToStaging),
+    callback: val => shouldUseStagingServer = lodashGet(val, 'shouldUseStagingServer', shouldDefaultToStaging),
 });
 
 let shouldFailAllRequests = false;
@@ -121,10 +121,13 @@ function xhr(command, data, type = CONST.NETWORK.METHOD.POST, shouldUseSecure =
 
     let apiRoot = shouldUseSecure ? CONFIG.EXPENSIFY.SECURE_EXPENSIFY_URL : CONFIG.EXPENSIFY.URL_API_ROOT;
 
-    if (shouldUseStagingServer(stagingServerToggleState)) {
-        apiRoot = shouldUseSecure ? CONFIG.EXPENSIFY.STAGING_SECURE_EXPENSIFY_URL : CONFIG.EXPENSIFY.STAGING_EXPENSIFY_URL;
+    if (shouldUseStagingServer) {
+        if (CONFIG.IS_USING_WEB_PROXY) {
+            apiRoot = shouldUseSecure ? proxyConfig.STAGING_SECURE : proxyConfig.STAGING;
+        } else {
+            apiRoot = shouldUseSecure ? CONFIG.EXPENSIFY.STAGING_SECURE_EXPENSIFY_URL : CONFIG.EXPENSIFY.STAGING_EXPENSIFY_URL;
+        }
     }
-
     return processHTTPRequest(`${apiRoot}api?command=${command}`, type, formData, data.canCancel);
 }
 
diff --git a/src/libs/shouldUseStagingServer/index.js b/src/libs/shouldUseStagingServer/index.js
deleted file mode 100644
index 745dd03b448..00000000000
--- a/src/libs/shouldUseStagingServer/index.js
+++ /dev/null
@@ -1,13 +0,0 @@
-import CONFIG from '../../CONFIG';
-
-/**
- * Helper method used to decide which API endpoint to call
- *
- * @param {Boolean} stagingServerToggleState
- * @returns {Boolean}
- */
-function shouldUseStagingServer(stagingServerToggleState) {
-    return CONFIG.IS_IN_STAGING && stagingServerToggleState;
-}
-
-export default shouldUseStagingServer;
diff --git a/src/libs/shouldUseStagingServer/index.native.js b/src/libs/shouldUseStagingServer/index.native.js
deleted file mode 100644
index 92baff89c83..00000000000
--- a/src/libs/shouldUseStagingServer/index.native.js
+++ /dev/null
@@ -1,13 +0,0 @@
-import * as Environment from '../Environment/Environment';
-
-/**
- * Helper method used to decide which API endpoint to call in the Native apps.
- * We build the staging native apps with production env config so we cannot rely on those values,
- * hence we will decide solely on the value of the shouldUseStagingServer value (always false in production).
- *
- * @param {Boolean} stagingServerToggleState
- * @returns {Boolean}
- */
-export default function shouldUseStagingServer(stagingServerToggleState) {
-    return !Environment.isDevelopment() && stagingServerToggleState;
-}
diff --git a/web/proxy.js b/web/proxy.js
index 768963d0810..4dc1a1018c1 100644
--- a/web/proxy.js
+++ b/web/proxy.js
@@ -1,21 +1,18 @@
 const http = require('http');
 const https = require('https');
+const proxyConfig = require('../config/proxyConfig');
 require('dotenv').config();
 
 if (process.env.USE_WEB_PROXY === 'false') {
     process.stdout.write('Skipping proxy as USE_WEB_PROXY was set to false.\n');
     process.exit();
 }
-
-let host = 'www.expensify.com';
-
-// If we are testing against the staging API then we must use the correct host here or nothing with work.
-if (/staging/.test(process.env.EXPENSIFY_URL)) {
-    host = 'staging.expensify.com';
-}
+const host = new URL(process.env.EXPENSIFY_URL || 'https://www.expensify.com').hostname;
+const stagingHost = new URL(process.env.STAGING_EXPENSIFY_URL || 'https://staging.expensify.com').hostname;
+const stagingSecureHost = new URL(process.env.STAGING_SECURE_EXPENSIFY_URL || 'https://staging-secure.expensify.com').hostname;
 
 // eslint-disable-next-line no-console
-console.log(`Creating proxy with host: ${host}`);
+console.log(`Creating proxy with host: ${host} for production API and ${stagingHost} for staging API`);
 
 /**
  * Local proxy server that hits the production endpoint
@@ -24,13 +21,35 @@ console.log(`Creating proxy with host: ${host}`);
  * environment that has no local API.
  */
 const server = http.createServer((request, response) => {
+    let hostname = host;
+    let requestPath = request.url;
+
+    /**
+     * When a request is matching a proxy config path we might direct it to a different host (e.g. staging)
+     * For requests matching proxy config patterns we replace the mapping url (prefix) with the actual path.
+     * This is done because the staging api root is only intended for the proxy,
+     * the actual server request must use the /api path.
+     * For example,
+     * /api?command=OpenReport => request sent to production server
+     * /staging-api?command=OpenReport => request sent to staging server
+     * /staging-secure-api?command=OpenReport => request sent to secure staging server
+     * /chat-attachments/46545... => request sent to production server
+     */
+    if (request.url.startsWith(proxyConfig.STAGING_SECURE)) {
+        hostname = stagingSecureHost;
+        requestPath = request.url.replace(proxyConfig.STAGING_SECURE, '/');
+    } else if (request.url.startsWith(proxyConfig.STAGING)) {
+        hostname = stagingHost;
+        requestPath = request.url.replace(proxyConfig.STAGING, '/');
+    }
+
     const proxyRequest = https.request({
-        hostname: host,
+        hostname,
         method: 'POST',
-        path: request.url,
+        path: requestPath,
         headers: {
             ...request.headers,
-            host,
+            host: hostname,
             'user-agent': request.headers['user-agent'].concat(' Development-NewDot/1.0'),
         },
         port: 443,