diff --git a/src/vs/platform/tunnel/common/tunnel.ts b/src/vs/platform/tunnel/common/tunnel.ts
index 9fd03586d78..82c93b7d5ad 100644
--- a/src/vs/platform/tunnel/common/tunnel.ts
+++ b/src/vs/platform/tunnel/common/tunnel.ts
@@ -126,6 +126,7 @@ export interface ITunnelService {
 
 	canTunnel(uri: URI): boolean;
 	openTunnel(addressProvider: IAddressProvider | undefined, remoteHost: string | undefined, remotePort: number, localPort?: number, elevateIfNeeded?: boolean, privacy?: string, protocol?: string): Promise<RemoteTunnel | undefined> | undefined;
+	getExistingTunnel(remoteHost: string, remotePort: number): Promise<RemoteTunnel | undefined>;
 	setEnvironmentTunnel(remoteHost: string, remotePort: number, localAddress: string, privacy: string, protocol: string): void;
 	closeTunnel(remoteHost: string, remotePort: number): Promise<void>;
 	setTunnelProvider(provider: ITunnelProvider | undefined): IDisposable;
@@ -282,6 +283,19 @@ export abstract class AbstractTunnelService implements ITunnelService {
 		}));
 	}
 
+	async getExistingTunnel(remoteHost: string, remotePort: number): Promise<RemoteTunnel | undefined> {
+		if (isAllInterfaces(remoteHost) || isLocalhost(remoteHost)) {
+			remoteHost = LOCALHOST_ADDRESSES[0];
+		}
+
+		const existing = this.getTunnelFromMap(remoteHost, remotePort);
+		if (existing) {
+			++existing.refcount;
+			return existing.value;
+		}
+		return undefined;
+	}
+
 	openTunnel(addressProvider: IAddressProvider | undefined, remoteHost: string | undefined, remotePort: number, localPort?: number, elevateIfNeeded: boolean = false, privacy?: string, protocol?: string): Promise<RemoteTunnel | undefined> | undefined {
 		this.logService.trace(`ForwardedPorts: (TunnelService) openTunnel request for ${remoteHost}:${remotePort} on local port ${localPort}.`);
 		if (!addressProvider) {
diff --git a/src/vs/workbench/electron-sandbox/window.ts b/src/vs/workbench/electron-sandbox/window.ts
index 24826e7f998..46307d1d7a4 100644
--- a/src/vs/workbench/electron-sandbox/window.ts
+++ b/src/vs/workbench/electron-sandbox/window.ts
@@ -769,13 +769,16 @@ export class NativeWindow extends Disposable {
 								return (await this.remoteAuthorityResolverService.resolveAuthority(remoteAuthority)).authority;
 							}
 						} : undefined;
-						const tunnel = await this.tunnelService.openTunnel(addressProvider, portMappingRequest.address, portMappingRequest.port);
+						let tunnel = await this.tunnelService.getExistingTunnel(portMappingRequest.address, portMappingRequest.port);
+						if (!tunnel) {
+							tunnel = await this.tunnelService.openTunnel(addressProvider, portMappingRequest.address, portMappingRequest.port);
+						}
 						if (tunnel) {
 							const addressAsUri = URI.parse(tunnel.localAddress);
 							const resolved = addressAsUri.scheme.startsWith(uri.scheme) ? addressAsUri : uri.with({ authority: tunnel.localAddress });
 							return {
 								resolved,
-								dispose: () => tunnel.dispose(),
+								dispose: () => tunnel?.dispose(),
 							};
 						}
 					}
diff --git a/src/vs/workbench/services/remote/common/remoteExplorerService.ts b/src/vs/workbench/services/remote/common/remoteExplorerService.ts
index 234f9eb50c0..1993302a228 100644
--- a/src/vs/workbench/services/remote/common/remoteExplorerService.ts
+++ b/src/vs/workbench/services/remote/common/remoteExplorerService.ts
@@ -473,6 +473,7 @@ export class TunnelModel extends Disposable {
 		this._register(this.tunnelService.onTunnelOpened(async (tunnel) => {
 			const key = makeAddress(tunnel.tunnelRemoteHost, tunnel.tunnelRemotePort);
 			if (!mapHasAddressLocalhostOrAllInterfaces(this.forwarded, tunnel.tunnelRemoteHost, tunnel.tunnelRemotePort)
+				&& !mapHasAddressLocalhostOrAllInterfaces(this.detected, tunnel.tunnelRemoteHost, tunnel.tunnelRemotePort)
 				&& !mapHasAddressLocalhostOrAllInterfaces(this.inProgress, tunnel.tunnelRemoteHost, tunnel.tunnelRemotePort)
 				&& tunnel.localAddress) {
 				const matchingCandidate = mapHasAddressLocalhostOrAllInterfaces(this._candidates ?? new Map(), tunnel.tunnelRemoteHost, tunnel.tunnelRemotePort);