diff --git a/src/vs/base/node/ports.ts b/src/vs/base/node/ports.ts
index 6ecdc71019c..9d3a8bdcfe1 100644
--- a/src/vs/base/node/ports.ts
+++ b/src/vs/base/node/ports.ts
@@ -63,6 +63,90 @@ function doFindFreePort(startPort: number, giveUpAfter: number, stride: number,
 	client.connect(startPort, '127.0.0.1');
 }
 
+// Reference: https://chromium.googlesource.com/chromium/src.git/+/refs/heads/main/net/base/port_util.cc#56
+export const BROWSER_RESTRICTED_PORTS: any = {
+    1: true,      // tcpmux
+    7: true,      // echo
+    9: true,      // discard
+    11: true,     // systat
+    13: true,     // daytime
+    15: true,     // netstat
+    17: true,     // qotd
+    19: true,     // chargen
+    20: true,     // ftp data
+    21: true,     // ftp access
+    22: true,     // ssh
+    23: true,     // telnet
+    25: true,     // smtp
+    37: true,     // time
+    42: true,     // name
+    43: true,     // nicname
+    53: true,     // domain
+    69: true,     // tftp
+    77: true,     // priv-rjs
+    79: true,     // finger
+    87: true,     // ttylink
+    95: true,     // supdup
+    101: true,    // hostriame
+    102: true,    // iso-tsap
+    103: true,    // gppitnp
+    104: true,    // acr-nema
+    109: true,    // pop2
+    110: true,    // pop3
+    111: true,    // sunrpc
+    113: true,    // auth
+    115: true,    // sftp
+    117: true,    // uucp-path
+    119: true,    // nntp
+    123: true,    // NTP
+    135: true,    // loc-srv /epmap
+    137: true,    // netbios
+    139: true,    // netbios
+    143: true,    // imap2
+    161: true,    // snmp
+    179: true,    // BGP
+    389: true,    // ldap
+    427: true,    // SLP (Also used by Apple Filing Protocol)
+    465: true,    // smtp+ssl
+    512: true,    // print / exec
+    513: true,    // login
+    514: true,    // shell
+    515: true,    // printer
+    526: true,    // tempo
+    530: true,    // courier
+    531: true,    // chat
+    532: true,    // netnews
+    540: true,    // uucp
+    548: true,    // AFP (Apple Filing Protocol)
+    554: true,    // rtsp
+    556: true,    // remotefs
+    563: true,    // nntp+ssl
+    587: true,    // smtp (rfc6409)
+    601: true,    // syslog-conn (rfc3195)
+    636: true,    // ldap+ssl
+    989: true,    // ftps-data
+    990: true,    // ftps
+    993: true,    // ldap+ssl
+    995: true,    // pop3+ssl
+    1719: true,   // h323gatestat
+    1720: true,   // h323hostcall
+    1723: true,   // pptp
+    2049: true,   // nfs
+    3659: true,   // apple-sasl / PasswordServer
+    4045: true,   // lockd
+    5060: true,   // sip
+    5061: true,   // sips
+    6000: true,   // X11
+    6566: true,   // sane-port
+    6665: true,   // Alternate IRC [Apple addition]
+    6666: true,   // Alternate IRC [Apple addition]
+    6667: true,   // Standard IRC [Apple addition]
+    6668: true,   // Alternate IRC [Apple addition]
+    6669: true,   // Alternate IRC [Apple addition]
+    6697: true,   // IRC + TLS
+    10080: true   // Amanda
+};
+
 /**
  * Uses listen instead of connect. Is faster, but if there is another listener on 0.0.0.0 then this will take 127.0.0.1 from that listener.
  */
diff --git a/src/vs/platform/remote/node/tunnelService.ts b/src/vs/platform/remote/node/tunnelService.ts
index 2a6c75f4532..322b743d2c9 100644
--- a/src/vs/platform/remote/node/tunnelService.ts
+++ b/src/vs/platform/remote/node/tunnelService.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as net from 'net';
-import { findFreePortFaster } from 'vs/base/node/ports';
+import { BROWSER_RESTRICTED_PORTS, findFreePortFaster } from 'vs/base/node/ports';
 import { NodeSocket } from 'vs/base/parts/ipc/node/ipc.net';
 import { nodeSocketFactory } from 'vs/platform/remote/node/nodeSocketFactory';
 
@@ -18,8 +18,18 @@ import { AbstractTunnelService, isAllInterfaces, ISharedTunnelsService as IShare
 import { ISignService } from 'vs/platform/sign/common/sign';
 
 async function createRemoteTunnel(options: IConnectionOptions, defaultTunnelHost: string, tunnelRemoteHost: string, tunnelRemotePort: number, tunnelLocalPort?: number): Promise<RemoteTunnel> {
-	const tunnel = new NodeRemoteTunnel(options, defaultTunnelHost, tunnelRemoteHost, tunnelRemotePort, tunnelLocalPort);
-	return tunnel.waitForReady();
+	let readyTunnel: NodeRemoteTunnel | undefined;
+	for (let attempts = 3; attempts; attempts--) {
+		if (readyTunnel) {
+			readyTunnel.dispose();
+		}
+		const tunnel = new NodeRemoteTunnel(options, defaultTunnelHost, tunnelRemoteHost, tunnelRemotePort, tunnelLocalPort);
+		readyTunnel = await tunnel.waitForReady();
+		if ((tunnelLocalPort && BROWSER_RESTRICTED_PORTS[tunnelLocalPort]) || !BROWSER_RESTRICTED_PORTS[readyTunnel.tunnelLocalPort]) {
+			break;
+		}
+	}
+	return readyTunnel!;
 }
 
 class NodeRemoteTunnel extends Disposable implements RemoteTunnel {