diff --git a/cli/src/tunnels/service_linux.rs b/cli/src/tunnels/service_linux.rs
index 3d1258a469a..b60d114dc46 100644
--- a/cli/src/tunnels/service_linux.rs
+++ b/cli/src/tunnels/service_linux.rs
@@ -17,7 +17,7 @@ use crate::{
 	constants::{APPLICATION_NAME, PRODUCT_NAME_LONG},
 	log,
 	state::LauncherPaths,
-	util::errors::{wrap, AnyError},
+	util::errors::{wrap, AnyError, DbusConnectFailedError},
 };
 
 use super::ServiceManager;
@@ -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. 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"))?;
+			.map_err(|e| DbusConnectFailedError(e.to_string()))?;
 		Ok(connection)
 	}
 
@@ -110,6 +110,10 @@ impl ServiceManager for SystemdService {
 
 		info!(self.log, "Tunnel service successfully started");
 
+		if std::env::var("SSH_CLIENT").is_ok() || std::env::var("SSH_TTY").is_ok() {
+			info!(self.log, "Tip: run `sudo loginctl enable-linger $USER` to ensure the service stays running after you disconnect.");
+		}
+
 		Ok(())
 	}
 
diff --git a/cli/src/util/errors.rs b/cli/src/util/errors.rs
index f1c4cbf5c22..6f4630d0c54 100644
--- a/cli/src/util/errors.rs
+++ b/cli/src/util/errors.rs
@@ -442,6 +442,26 @@ macro_rules! makeAnyError {
     };
 }
 
+#[derive(Debug)]
+pub struct DbusConnectFailedError(pub String);
+
+impl Display for DbusConnectFailedError {
+	fn fmt(&self, f: &mut std::fmt::Formatter) -> std::fmt::Result {
+		let mut str = String::new();
+		str.push_str("Error creating dbus session. This command uses systemd for managing services, you should check that systemd is installed and under your user.");
+
+		if std::env::var("WSL_DISTRO_NAME").is_ok() {
+			str.push_str("\n\nTo enable systemd on WSL, check out: https://devblogs.microsoft.com/commandline/systemd-support-is-now-available-in-wsl/.\n\n");
+		}
+
+		str.push_str("If running `systemctl status` works, systemd is ok, but your session dbus may not be. You might need to:\n\n- Install the `dbus-user-session` package, and reboot if it was not installed\n- Start the user dbus session with `systemctl --user enable dbus --now`.\n\nThe error encountered was: ");
+		str.push_str(&self.0);
+		str.push('\n');
+
+		write!(f, "{}", str)
+	}
+}
+
 /// Internal errors in the VS Code CLI.
 /// Note: other error should be migrated to this type gradually
 #[derive(Error, Debug)]
@@ -522,7 +542,8 @@ makeAnyError!(
 	MissingHomeDirectory,
 	OAuthError,
 	InvalidRpcDataError,
-	CodeError
+	CodeError,
+	DbusConnectFailedError
 );
 
 impl From<reqwest::Error> for AnyError {