diff --git a/espanso/src/cli/launcher/mod.rs b/espanso/src/cli/launcher/mod.rs
index dd6f0db..9be664a 100644
--- a/espanso/src/cli/launcher/mod.rs
+++ b/espanso/src/cli/launcher/mod.rs
@@ -94,6 +94,24 @@ fn launcher_main(args: CliModuleArgs) -> i32 {
       },
     });
 
+  let is_auto_start_page_enabled = !preferences.has_selected_auto_start_option();
+  let preferences_clone = preferences.clone();
+  let auto_start_handler = Box::new(move |auto_start| {
+    preferences_clone.set_has_selected_auto_start_option(true);
+
+    if auto_start {
+      match util::configure_auto_start(true) {
+        Ok(_) => true,
+        Err(error) => {
+          eprintln!("Service register returned error: {}", error);
+          false
+        }
+      }
+    } else {
+      true
+    }
+  });
+
   let is_add_path_page_enabled =
     if cfg!(not(target_os = "linux")) && !preferences.has_completed_wizard() {
       if cfg!(target_os = "macos") {
@@ -133,6 +151,7 @@ fn launcher_main(args: CliModuleArgs) -> i32 {
     || is_move_bundle_page_enabled
     || is_legacy_version_page_enabled
     || is_migrate_page_enabled
+    || is_auto_start_page_enabled
     || is_add_path_page_enabled
     || is_accessibility_page_enabled
     || is_wrong_edition_page_enabled
@@ -144,6 +163,7 @@ fn launcher_main(args: CliModuleArgs) -> i32 {
       is_legacy_version_page_enabled,
       is_wrong_edition_page_enabled,
       is_migrate_page_enabled,
+      is_auto_start_page_enabled,
       is_add_path_page_enabled,
       is_accessibility_page_enabled,
       window_icon_path: icon_paths
@@ -162,6 +182,7 @@ fn launcher_main(args: CliModuleArgs) -> i32 {
       handlers: WizardHandlers {
         is_legacy_version_running: Some(is_legacy_version_running_handler),
         backup_and_migrate: Some(backup_and_migrate_handler),
+        auto_start: Some(auto_start_handler),
         add_to_path: Some(add_to_path_handler),
         enable_accessibility: Some(enable_accessibility_handler),
         is_accessibility_enabled: Some(is_accessibility_enabled_handler),
diff --git a/espanso/src/cli/launcher/util.rs b/espanso/src/cli/launcher/util.rs
index 3a93e0c..e4fd3b0 100644
--- a/espanso/src/cli/launcher/util.rs
+++ b/espanso/src/cli/launcher/util.rs
@@ -19,13 +19,14 @@
 
 use std::{path::Path, process::Command};
 
-use anyhow::Result;
+use anyhow::{bail, Result};
 use espanso_path::Paths;
 use thiserror::Error;
 
 use crate::{
   exit_code::{MIGRATE_CLEAN_FAILURE, MIGRATE_DIRTY_FAILURE},
   lock::acquire_legacy_lock,
+  util::set_command_flags,
 };
 
 pub fn is_legacy_version_running(runtime_path: &Path) -> bool {
@@ -106,3 +107,26 @@ pub fn show_already_running_warning() -> Result<()> {
   child.wait()?;
   Ok(())
 }
+
+pub fn configure_auto_start(auto_start: bool) -> Result<()> {
+  let espanso_exe_path = std::env::current_exe()?;
+  let mut command = Command::new(&espanso_exe_path.to_string_lossy().to_string());
+  let mut args = vec!["service"];
+  if auto_start {
+    args.push("register");
+  } else {
+    args.push("unregister");
+  }
+
+  command.args(&args);
+  set_command_flags(&mut command);
+
+  let mut child = command.spawn()?;
+  let result = child.wait()?;
+
+  if result.success() {
+    Ok(())
+  } else {
+    bail!("service registration returned non-zero exit code");
+  }
+}
diff --git a/espanso/src/cli/service/win.rs b/espanso/src/cli/service/win.rs
index 3fa25dd..f41b383 100644
--- a/espanso/src/cli/service/win.rs
+++ b/espanso/src/cli/service/win.rs
@@ -24,6 +24,7 @@ use std::path::{Path, PathBuf};
 use std::process::Command;
 use thiserror::Error;
 
+use crate::util::set_command_flags;
 use crate::{error_eprintln, warn_eprintln};
 
 pub fn register() -> Result<()> {
@@ -145,13 +146,15 @@ fn create_shortcut_target_file(
   target_path: &Path,
   arguments: &str,
 ) -> Result<()> {
-  let output = Command::new("powershell")
-            .arg("-c")
-            .arg("$WshShell = New-Object -comObject WScript.Shell; $Shortcut = $WshShell.CreateShortcut($env:SHORTCUT_PATH); $Shortcut.TargetPath = $env:TARGET_PATH; $Shortcut.Arguments = $env:TARGET_ARGS; $Shortcut.Save()")
-            .env("SHORTCUT_PATH", shortcut_path.to_string_lossy().to_string())
-            .env("TARGET_PATH", target_path.to_string_lossy().to_string())
-            .env("TARGET_ARGS", arguments)
-            .output()?;
+  let mut command = Command::new("powershell");
+  command.arg("-c");
+  command.arg("$WshShell = New-Object -comObject WScript.Shell; $Shortcut = $WshShell.CreateShortcut($env:SHORTCUT_PATH); $Shortcut.TargetPath = $env:TARGET_PATH; $Shortcut.Arguments = $env:TARGET_ARGS; $Shortcut.Save()");
+  command.env("SHORTCUT_PATH", shortcut_path.to_string_lossy().to_string());
+  command.env("TARGET_PATH", target_path.to_string_lossy().to_string());
+  command.env("TARGET_ARGS", arguments);
+
+  set_command_flags(&mut command);
+  let output = command.output()?;
 
   if !output.status.success() {
     return Err(ShortcutError::PowershellNonZeroExitCode.into());
diff --git a/espanso/src/preferences/default.rs b/espanso/src/preferences/default.rs
index e7747c1..d04ccca 100644
--- a/espanso/src/preferences/default.rs
+++ b/espanso/src/preferences/default.rs
@@ -28,6 +28,7 @@ const HAS_COMPLETED_WIZARD_KEY: &str = "has_completed_wizard";
 const HAS_DISPLAYED_WELCOME_KEY: &str = "has_displayed_welcome";
 const SHOULD_DISPLAY_TROUBLESHOOT_FOR_NON_FATAL_ERRORS: &str =
   "should_display_troubleshoot_for_non_fatal_errors";
+const HAS_SELECTED_AUTO_START_OPTION: &str = "has_selected_auto_start_option";
 
 #[derive(Clone)]
 pub struct DefaultPreferences<KVSType: KVS> {
@@ -80,4 +81,12 @@ impl<KVSType: KVS> Preferences for DefaultPreferences<KVSType> {
   fn set_should_display_troubleshoot_for_non_fatal_errors(&self, value: bool) {
     self.set(SHOULD_DISPLAY_TROUBLESHOOT_FOR_NON_FATAL_ERRORS, value);
   }
+
+  fn has_selected_auto_start_option(&self) -> bool {
+    self.get(HAS_SELECTED_AUTO_START_OPTION).unwrap_or(false)
+  }
+
+  fn set_has_selected_auto_start_option(&self, value: bool) {
+    self.set(HAS_SELECTED_AUTO_START_OPTION, value);
+  }
 }
diff --git a/espanso/src/preferences/mod.rs b/espanso/src/preferences/mod.rs
index 569fb37..5739217 100644
--- a/espanso/src/preferences/mod.rs
+++ b/espanso/src/preferences/mod.rs
@@ -31,6 +31,9 @@ pub trait Preferences: Send + Sync + Clone {
 
   fn should_display_troubleshoot_for_non_fatal_errors(&self) -> bool;
   fn set_should_display_troubleshoot_for_non_fatal_errors(&self, value: bool);
+
+  fn has_selected_auto_start_option(&self) -> bool;
+  fn set_has_selected_auto_start_option(&self, value: bool);
 }
 
 pub fn get_default(runtime_dir: &Path) -> Result<impl Preferences> {