diff --git a/lib/_http_client.js b/lib/_http_client.js
index b81ffa1cefc573..4a9d199ba398c7 100644
--- a/lib/_http_client.js
+++ b/lib/_http_client.js
@@ -36,6 +36,7 @@ const {
   StringPrototypeCharCodeAt,
   StringPrototypeIncludes,
   StringPrototypeIndexOf,
+  StringPrototypeStartsWith,
   StringPrototypeToUpperCase,
   Symbol,
   TypedArrayPrototypeSlice,
@@ -270,6 +271,17 @@ function ClientRequest(input, options, cb) {
 
     if (host && !this.getHeader('host') && setHost) {
       let hostHeader = host;
+      let hostHeaderPort = port;
+
+      // Prevent potential domain fronting misjudgement when using proxy
+      // Overwrite the default Host request header with the host of path
+      if (!StringPrototypeStartsWith(this.path, '/')) {
+        const proxyURL = new URL(RegExpPrototypeTest(
+          /^[^:]+:\/\//, this.path) ? this.path : `http://${this.path}`);
+        hostHeader = proxyURL.hostname;
+        hostHeaderPort = proxyURL.port || (
+          proxyURL.protocol === 'https:' ? '443' : '80');
+      }
 
       // For the Host header, ensure that IPv6 addresses are enclosed
       // in square brackets, as defined by URI formatting
@@ -281,8 +293,8 @@ function ClientRequest(input, options, cb) {
         hostHeader = `[${hostHeader}]`;
       }
 
-      if (port && +port !== defaultPort) {
-        hostHeader += ':' + port;
+      if (hostHeaderPort && +hostHeaderPort !== defaultPort) {
+        hostHeader += ':' + hostHeaderPort;
       }
       this.setHeader('Host', hostHeader);
     }
diff --git a/test/parallel/test-tls-over-http-tunnel.js b/test/parallel/test-tls-over-http-tunnel.js
index b26cf7872f6582..6fd552a1e30cc2 100644
--- a/test/parallel/test-tls-over-http-tunnel.js
+++ b/test/parallel/test-tls-over-http-tunnel.js
@@ -61,7 +61,8 @@ const proxy = net.createServer((clientSocket) => {
                          `CONNECT localhost:${server.address().port} ` +
                          'HTTP/1.1\r\n' +
                          'Proxy-Connections: keep-alive\r\n' +
-                         `Host: localhost:${proxy.address().port}\r\n` +
+                         // Match header Host with destination Host
+                         `Host: localhost:${server.address().port}\r\n` +
                          'Connection: close\r\n\r\n');
 
       console.log('PROXY: got CONNECT request');