diff --git a/cli/src/commands/args.rs b/cli/src/commands/args.rs
index 92decf5ff0e..5d23bd634fb 100644
--- a/cli/src/commands/args.rs
+++ b/cli/src/commands/args.rs
@@ -6,7 +6,7 @@
 use std::{fmt, path::PathBuf};
 
 use crate::{constants, log, options, tunnels::code_server::CodeServerArgs};
-use clap::{ValueEnum, Args, Parser, Subcommand};
+use clap::{Args, Parser, Subcommand, ValueEnum};
 use const_format::concatcp;
 
 const CLI_NAME: &str = concatcp!(constants::PRODUCT_NAME_LONG, " CLI");
diff --git a/cli/src/commands/tunnels.rs b/cli/src/commands/tunnels.rs
index b8d7b0b60bd..3f29ee7020e 100644
--- a/cli/src/commands/tunnels.rs
+++ b/cli/src/commands/tunnels.rs
@@ -4,7 +4,8 @@
  *--------------------------------------------------------------------------------------------*/
 
 use async_trait::async_trait;
-use base64::{Engine as _, engine::general_purpose as b64};
+use base64::{engine::general_purpose as b64, Engine as _};
+use serde::Serialize;
 use sha2::{Digest, Sha256};
 use std::{str::FromStr, time::Duration};
 use sysinfo::Pid;
@@ -247,8 +248,14 @@ pub async fn kill(ctx: CommandContext) -> Result<i32, AnyError> {
 	.map_err(|e| e.into())
 }
 
+#[derive(Serialize)]
+pub struct StatusOutput {
+	pub tunnel: Option<protocol::singleton::TunnelState>,
+	pub service_installed: bool,
+}
+
 pub async fn status(ctx: CommandContext) -> Result<i32, AnyError> {
-	let status = do_single_rpc_call::<_, protocol::singleton::Status>(
+	let tunnel_status = do_single_rpc_call::<_, protocol::singleton::Status>(
 		&ctx.paths.tunnel_lockfile(),
 		ctx.log.clone(),
 		protocol::singleton::METHOD_STATUS,
@@ -256,17 +263,24 @@ pub async fn status(ctx: CommandContext) -> Result<i32, AnyError> {
 	)
 	.await;
 
-	match status {
-		Err(CodeError::NoRunningTunnel) => {
-			ctx.log.result(CodeError::NoRunningTunnel.to_string());
-			Ok(1)
-		}
-		Err(e) => Err(e.into()),
-		Ok(s) => {
-			ctx.log.result(serde_json::to_string(&s).unwrap());
-			Ok(0)
-		}
-	}
+	let service_installed = create_service_manager(ctx.log.clone(), &ctx.paths)
+		.is_installed()
+		.await
+		.unwrap_or(false);
+
+	ctx.log.result(
+		serde_json::to_string(&StatusOutput {
+			service_installed,
+			tunnel: match tunnel_status {
+				Ok(s) => Some(s.tunnel),
+				Err(CodeError::NoRunningTunnel) => None,
+				Err(e) => return Err(e.into()),
+			},
+		})
+		.unwrap(),
+	);
+
+	Ok(0)
 }
 
 /// Removes unused servers.
diff --git a/cli/src/lib.rs b/cli/src/lib.rs
index 93777852df2..b2e23cb4d69 100644
--- a/cli/src/lib.rs
+++ b/cli/src/lib.rs
@@ -18,8 +18,8 @@ pub mod tunnels;
 pub mod update_service;
 pub mod util;
 
-mod download_cache;
 mod async_pipe;
+mod download_cache;
 mod json_rpc;
 mod msgpack_rpc;
 mod rpc;
diff --git a/cli/src/tunnels/service.rs b/cli/src/tunnels/service.rs
index 31bf6890996..dba68f3b614 100644
--- a/cli/src/tunnels/service.rs
+++ b/cli/src/tunnels/service.rs
@@ -41,6 +41,9 @@ pub trait ServiceManager {
 	/// Show logs from the running service to standard out.
 	async fn show_logs(&self) -> Result<(), AnyError>;
 
+	/// Gets whether the tunnel service is installed.
+	async fn is_installed(&self) -> Result<bool, AnyError>;
+
 	/// Unregisters the current executable as a service.
 	async fn unregister(&self) -> Result<(), AnyError>;
 }
diff --git a/cli/src/tunnels/service_linux.rs b/cli/src/tunnels/service_linux.rs
index 725b72a8d6d..3d1258a469a 100644
--- a/cli/src/tunnels/service_linux.rs
+++ b/cli/src/tunnels/service_linux.rs
@@ -40,7 +40,7 @@ impl SystemdService {
 	async fn connect() -> Result<Connection, AnyError> {
 		let connection = Connection::session()
 			.await
-			.map_err(|e| wrap(e, "error creating dbus session"))?;
+			.map_err(|e| wrap(e, "Error creating dbus session. This command uses systemd for managing services, you should check that systemd is installed and running as a user. If it's already installed, you may need to:\n\n- Install the `dbus-user-session` package and reboot\n- Start the user dbus session with `systemctl --user enable dbus --now`. \n\nThe error encountered was"))?;
 		Ok(connection)
 	}
 
@@ -113,6 +113,20 @@ impl ServiceManager for SystemdService {
 		Ok(())
 	}
 
+	async fn is_installed(&self) -> Result<bool, AnyError> {
+		let connection = SystemdService::connect().await?;
+		let proxy = SystemdService::proxy(&connection).await?;
+		let state = proxy
+			.get_unit_file_state(SystemdService::service_name_string())
+			.await;
+
+		if let Ok(s) = state {
+			Ok(s == "enabled")
+		} else {
+			Ok(false)
+		}
+	}
+
 	async fn run(
 		self,
 		launcher_paths: crate::state::LauncherPaths,
@@ -219,6 +233,8 @@ trait SystemdManagerDbus {
 		force: bool,
 	) -> zbus::Result<(bool, Vec<(String, String, String)>)>;
 
+	fn get_unit_file_state(&self, file: String) -> zbus::Result<String>;
+
 	fn link_unit_files(
 		&self,
 		files: Vec<String>,
diff --git a/cli/src/tunnels/service_macos.rs b/cli/src/tunnels/service_macos.rs
index dcc676ffce5..2d0a23f8cb2 100644
--- a/cli/src/tunnels/service_macos.rs
+++ b/cli/src/tunnels/service_macos.rs
@@ -75,6 +75,11 @@ impl ServiceManager for LaunchdService {
 		handle.run_service(self.log, launcher_paths).await
 	}
 
+	async fn is_installed(&self) -> Result<bool, AnyError> {
+		let cmd = capture_command_and_check_status("launchctl", &["list"]).await?;
+		Ok(String::from_utf8_lossy(&cmd.stdout).contains(&get_service_label()))
+	}
+
 	async fn unregister(&self) -> Result<(), crate::util::errors::AnyError> {
 		let service_file = get_service_file_path()?;
 
diff --git a/cli/src/tunnels/service_windows.rs b/cli/src/tunnels/service_windows.rs
index 3404b4ed52c..427eddd620d 100644
--- a/cli/src/tunnels/service_windows.rs
+++ b/cli/src/tunnels/service_windows.rs
@@ -114,6 +114,11 @@ impl CliServiceManager for WindowsService {
 		Ok(())
 	}
 
+	async fn is_installed(&self) -> Result<bool, AnyError> {
+		let key = WindowsService::open_key()?;
+		Ok(key.get_raw_value(TUNNEL_ACTIVITY_NAME).is_ok())
+	}
+
 	async fn unregister(&self) -> Result<(), AnyError> {
 		let key = WindowsService::open_key()?;
 		key.delete_value(TUNNEL_ACTIVITY_NAME)
diff --git a/cli/src/util/tar.rs b/cli/src/util/tar.rs
index 77dd67abbb0..248f63f9720 100644
--- a/cli/src/util/tar.rs
+++ b/cli/src/util/tar.rs
@@ -6,7 +6,7 @@ use crate::util::errors::{wrap, WrappedError};
 
 use flate2::read::GzDecoder;
 use std::fs;
-use std::io::{Seek, SeekFrom};
+use std::io::Seek;
 use std::path::{Path, PathBuf};
 use tar::Archive;
 
@@ -65,7 +65,7 @@ where
 
 	// reset since skip logic read the tar already:
 	tar_gz
-		.seek(SeekFrom::Start(0))
+		.rewind()
 		.map_err(|e| wrap(e, "error resetting seek position"))?;
 
 	let tar = GzDecoder::new(tar_gz);
diff --git a/cli/src/util/zipper.rs b/cli/src/util/zipper.rs
index 84eec040b0e..45dd3b7e85d 100644
--- a/cli/src/util/zipper.rs
+++ b/cli/src/util/zipper.rs
@@ -88,8 +88,7 @@ where
 			use std::io::Read;
 			use std::os::unix::ffi::OsStringExt;
 
-			if matches!(file.unix_mode(), Some(mode) if mode & (S_IFLNK as u32) == (S_IFLNK as u32))
-			{
+			if matches!(file.unix_mode(), Some(mode) if mode & S_IFLNK == S_IFLNK) {
 				let mut link_to = Vec::new();
 				file.read_to_end(&mut link_to).map_err(|e| {
 					wrap(
diff --git a/src/vs/platform/remoteTunnel/node/remoteTunnelService.ts b/src/vs/platform/remoteTunnel/node/remoteTunnelService.ts
index 9b73eece6ba..e3cee9778a2 100644
--- a/src/vs/platform/remoteTunnel/node/remoteTunnelService.ts
+++ b/src/vs/platform/remoteTunnel/node/remoteTunnelService.ts
@@ -165,7 +165,7 @@ export class RemoteTunnelService extends Disposable implements IRemoteTunnelServ
 	}
 
 	async startTunnel(session: IRemoteTunnelSession): Promise<TunnelStatus> {
-		if (isSameSession(session, this._session)) {
+		if (isSameSession(session, this._session) && this._tunnelStatus.type !== 'disconnected') {
 			return this._tunnelStatus;
 		}
 		this.setSession(session);
@@ -195,7 +195,7 @@ export class RemoteTunnelService extends Disposable implements IRemoteTunnelServ
 			}
 		};
 		try {
-			await this.runCodeTunneCommand('stop', ['kill'], onOutput);
+			await this.runCodeTunnelCommand('stop', ['kill'], onOutput);
 		} catch (e) {
 			this._logger.error(e);
 		}
@@ -213,26 +213,35 @@ export class RemoteTunnelService extends Disposable implements IRemoteTunnelServ
 		}
 
 		let isAttached = false;
+		let output = '';
 
 		const onOutput = (a: string, isErr: boolean) => {
 			if (isErr) {
 				this._logger.error(a);
 			} else {
-				this._logger.info(a);
+				output += a;
 			}
 			if (!this.environmentService.isBuilt && a.startsWith('   Compiling')) {
 				this.setTunnelStatus(TunnelStates.connecting(localize('remoteTunnelService.building', 'Building CLI from sources')));
 			}
 		};
 
-		const statusProcess = this.runCodeTunneCommand('status', ['status'], onOutput);
+		const statusProcess = this.runCodeTunnelCommand('status', ['status'], onOutput);
 		this._tunnelProcess = statusProcess;
 		try {
-			const status = await statusProcess;
+			await statusProcess;
 			if (this._tunnelProcess !== statusProcess) {
 				return;
 			}
-			isAttached = status === 0;
+
+			// split and find the line, since in dev builds additional noise is
+			// added by cargo to the output.
+			const status: {
+				service_installed: boolean;
+				tunnel: object | null;
+			} = JSON.parse(output.trim().split('\n').find(l => l.startsWith('{'))!);
+
+			isAttached = !!status.tunnel;
 			this._logger.info(isAttached ? 'Other tunnel running, attaching...' : 'No other tunnel running');
 			if (!isAttached && !this._session) {
 				this._tunnelProcess = undefined;
@@ -255,7 +264,7 @@ export class RemoteTunnelService extends Disposable implements IRemoteTunnelServ
 				a = a.replaceAll(token, '*'.repeat(4));
 				onOutput(a, isErr);
 			};
-			const loginProcess = this.runCodeTunneCommand('login', ['user', 'login', '--provider', session.providerId, '--access-token', token, '--log', LogLevelToString(this._logger.getLevel())], onLoginOutput);
+			const loginProcess = this.runCodeTunnelCommand('login', ['user', 'login', '--provider', session.providerId, '--access-token', token, '--log', LogLevelToString(this._logger.getLevel())], onLoginOutput);
 			this._tunnelProcess = loginProcess;
 			try {
 				await loginProcess;
@@ -286,7 +295,7 @@ export class RemoteTunnelService extends Disposable implements IRemoteTunnelServ
 		if (this._preventSleep()) {
 			args.push('--no-sleep');
 		}
-		const serveCommand = this.runCodeTunneCommand('tunnel', args, (message: string, isErr: boolean) => {
+		const serveCommand = this.runCodeTunnelCommand('tunnel', args, (message: string, isErr: boolean) => {
 			if (isErr) {
 				this._logger.error(message);
 			} else {
@@ -315,7 +324,7 @@ export class RemoteTunnelService extends Disposable implements IRemoteTunnelServ
 		});
 	}
 
-	private runCodeTunneCommand(logLabel: string, commandArgs: string[], onOutput: (message: string, isError: boolean) => void = () => { }): CancelablePromise<number> {
+	private runCodeTunnelCommand(logLabel: string, commandArgs: string[], onOutput: (message: string, isError: boolean) => void = () => { }): CancelablePromise<number> {
 		return createCancelablePromise<number>(token => {
 			return new Promise((resolve, reject) => {
 				if (token.isCancellationRequested) {